Every Episode of Monk, Ranked

The original blue-sky show balanced darkness and humor better than any of its successors.

It’s a jungle out there. Randy Newman’s jaunty theme song warns us as much at the beginning of (nearly) every episode of Monk. Across eight seasons, the USA procedural showed us just how dirty and dangerous the world is — or at least that’s how it appears through the eyes of its germophobic main character, Adrian Monk. Tony Shalhoub plays the titular detective with severe obsessive-compulsive disorder, who was discharged from the San Francisco police department following a mental breakdown when his wife, Trudy (Melora Hardin), was murdered. With the help of Captain Leland Stottlemeyer (Ted Levine), Lieutenant Randy Disher (Jason Gray-Stanford), and a spunky assistant — originally Sharona Fleming (Bitty Schram) and later Natalie Teeger (Traylor Howard) — and the support of his beloved psychiatrists Dr. Kroger (Stanley Kamel) and Dr. Bell (Hector Elizondo), Mr. Monk is called in as a consultant to solve the cases that stump the SFPD. He does this work in the hopes of getting reinstated to the police force and, in some ways, to atone for the fact that Trudy’s murder still remains a mystery. If it’s not clear from that description, it’s also a really funny show!

Monk is the progenitor of the blue-sky shows, a term given to the breezy procedurals that populated the USA Network during the mid-aughts to distinguish them from the grittier dramas found elsewhere on basic cable. Monk’s writing staff was (mostly) able to balance its dark premise with light humor, setting the template for shows like Psych, Burn Notice, and Suits. The show’s creator, Andy Breckman, wrote for Late Night With David Letterman and Saturday Night Live before developing Monk and brought on writers with a similar background in comedy in addition to more traditional mystery writers. The team wrung every ounce of comedy and drama out of their lead’s fears and compulsions, tempering his sadness and vulnerability with a wry yet goofy sense of humor. The show is at its best when a big bully underestimates Monk, dismissing him as a sad, strange little man, only to be outsmarted with a smirk and a, “Here’s what happened.”

Ultimately, though, Monk is a show about love. Monk’s love for Trudy compels him to keep working, but the people who love Monk help keep him living. A new movie on Peacock, Mr. Monk’s Last Case: A Monk Movie, doubles down on that theme, finding Monk the most depressed we’ve ever seen him after COVID lockdown. When Trudy’s daughter, Molly (Caitlin McGee), needs Monk’s help solving her fiancé’s mysterious death, Monk is reminded how much he matters to the people in his life. The show’s signature blend of dark humor is still potent nearly 15 years after its series finale aired, if not more so. As several of his friends point out in Mr. Monk’s Last Case, post-COVID the whole world is living like Mr. Monk. To get excited for the movie, now streaming on Peacock, I ranked every episode of the series, with that core thesis in mind. You’ll thank me later.

119. Season 1, Episode 6: “Mr. Monk Goes to the Asylum”

It’s inevitable that a show occasionally has to break up its core cast, usually due to budget restraints or scheduling conflicts. Monk has a few episodes where Mr. Monk is separated from the captain et al., and they’re usually some of the weakest. “Mr. Monk Goes to the Asylum” is the weakest of the bunch. Add in a half-assed bad doctor villain and an unusually passive Mr. Monk, and you get this, the weakest of the weak of the series. Monk is institutionalized after accidentally breaking into Trudy’s old house in a fugue state, where he figures out that the hospital’s director, Dr. Lancaster (Dennis Boutsikaris), killed his partner several years ago and framed a patient for it. Solving the mystery is just kind of frustrating rather than rewarding, as Dr. Lancaster manipulates Monk into thinking he’s going crazy, but the solution isn’t especially clever or outrageous. Without the grounding presence of Stottlemeyer and Disher, Monk’s heightened character has nothing to bounce against. Quite the contrary, in fact, he’s surrounded by other heightened characters in his fellow patients, which pull focus from Monk without much payoff. It’s a shame, because Kevin Nealon is doing great work guest starring as a fellow patient who’s a pathological liar.

118. Season 4, Episode 6: “Mr. Monk and Mrs. Monk”

Mr. Monk makes a lot of false starts on solving Trudy’s murder over the course of the show’s eight seasons, and it’s always a bummer, but this episode is a bummer without any satisfying payoff. Natalie sees a woman who looks just like Trudy in a diner and overhears that she faked her own death when she was being threatened over a story she was working on about corruption in the local dockworkers union, and now she needs to get back some documents from her co-writer. When the man she was talking to turns up murdered, several clues at the crime scene point to Trudy. The murder is ancillary to the actual mystery of whether or not Trudy is alive, and it’s never all that convincing. At no point did we actually think that Trudy was alive, so when we learn that she was a doppelgänger hired by the union leaders, the reveal doesn’t feel interesting or clever. Many Monk episodes are sad — this one is sad and boring.

117. Season 8, Episode 9: “Happy Birthday, Mr. Monk”

There is just way too much going on in this episode and it never quite gels together. Natalie is trying to throw Monk a surprise 50th birthday party, which he keeps thwarting. A maintenance man is killed in an apparent accident, but Monk isn’t convinced. John Carroll Lynch guest stars as an inventor of a self-cleaning vacuum whose patent attorney is murdered, and Monk figures out that the attorney stole the idea for the vacuum from the maintenance man and then the inventor killed the attorney to keep all the money himself. And I haven’t even mentioned the introduction of T.K. Jensen (Virginia Madsen) yet, who will become Captain Stottlemeyer’s love interest for the remainder of the series. Plus, while it’s a common joke that you can tell who a procedural’s murderer of the week is by recognizing the famous guest star, it’s especially obvious when the famous guest star is John Carroll Lynch. The fact that the solution is a common brain-teaser — Lynch’s character poisoned the ice cubes in his attorney’s drink, which would kill him once they melted — is just insulting.

116. Season 6, Episode 6: “Mr. Monk and the Buried Treasure”

In a session, Dr. Kroger admits to Monk that his son Troy (Cody McMains) has been getting into trouble at school. Later, Troy and his friends show up at Monk’s door asking for help solving a treasure map that he says is for school, but he actually found it in a car next to a dead guy who appears to have robbed a bank and then had a heart attack. Monk, of course, figures it out quickly, but it turns out the robber had a partner who follows them and buries Monk and Troy alive. Troy talks Monk through his extreme claustrophobia until the captain and Randy arrive to rescue them. The experience is so formative for Troy that he tells his dad he has decided he wants to be a therapist.

Setting aside Dr. Kroger’s egregious ethical breaches here, it’s just not that interesting. We have no reason to care enough about Troy to be moved by his growth in this episode — it’s only our second time meeting him — and other episodes have done a better job playing off Monk’s claustrophobia. This isn’t even the first time he’s been buried alive! (See: “Mr. Monk vs. the Cobra.”)

115. Season 2, Episode 3: “Mr. Monk Goes to the Ballgame”

When a billionaire and his wife are murdered, Monk figures out that she was the prime target. He tracks down a pro baseball player she was having an affair with, Scott Gregorio (Christopher Wiehl), who had been about to beat the single-season home-run record but is so distraught by her death that he’s hit a slump. Monk quickly determines that Gregorio is a good guy who didn’t kill his girlfriend. He even comes to help Sharona’s son Benjy (Kane Ritchotte) with his Little League games. Instead, it was a memorabilia collector (a pre–The Office Rainn Wilson) who wanted to sell the previous record-breaking ball, which would become worthless if Gregorio beat it.

There are some funny moments here, especially the parallels between the Little League and the Majors, but it’s always kind of a letdown when the murderer turns out to be someone completely random. It’s more fun when we at least have the possibility of figuring out the mystery ourselves before Monk does. Plus, Stottlemeyer is a real dick at the Little League game, and while we love our Captain a little gruff, yelling at 11-year-olds is a bridge too far.

114. Season 8, Episode 6: “Mr. Monk and the Critic”

Most of this episode, in which Natalie has to convince Monk and the team that a theater critic, John Hannigan (Dylan Baker), who gave her daughter Julie (Emmy Clarke) a bad review, is the murderer they’re looking for, is perfectly fine. There are even some fun moments, like when Monk is dazzled by the theater’s fastidious bathroom attendant (Bernie Kopell), but the opening shot is so jarring that it sets a sour tone for the remaining 40ish minutes. It’s filmed as a continuous shot from Hannigan’s POV, showing him meeting Callie, played by Erin Cahill, in her hotel room and proposing to her on the balcony before pushing her over the railing. I appreciate a hard swing of a directing choice, but Cahill is tasked with a lot of heavy lifting here, acting-wise, since the camera is trained on her face the whole time, and she doesn’t nail it. Rather than creative, it just looks cringe.

113. Season 5, Episode 15: “Mr. Monk and the Really, Really Dead Guy”

The FBI are called in when a serial killer is on the loose in San Francisco and they’re given 36 hours before he’ll strike again. The Feds are arrogant and mean, taunting Monk for his luddite tendencies and berating him for focusing on another case — a pharmaceutical rep killed inside a gas station — instead of the so-called Six-Way Killer. It’s a good thing he did, though, because he figures out that the 36-hour deadline was a ploy to keep the cops from investigating the woman’s death and checking out the contents of her stomach, which would identify a distinctive dessert that she ate the night she was murdered.

Mr. Monk and his brain versus the Feds’ fancy technology is a fun face-off, but there’s a reason Monk doesn’t typically do serial killers. Tracking down a cold, random killer Criminal Minds–style is a much different vibe from the more Columbo-y deducing of motive, means, and opportunity. Though it ends up not to actually be a serial killer, that’s the tone we’re steeped in for most of the episode, and it just doesn’t feel like Monk.

112. Season 1, Episode 5: “Mr. Monk Goes to the Carnival”

Police procedurals inevitably take a cop’s-eye view of the world, with all the baggage that entails. Monk was never going to have a nuanced perception of policing, but it is still pretty hard to stomach this story line about trying to exonerate a cop with a history of violence. To the writers’ credit, Monk himself is disgusted with the accused Lieutenant Kirk (Stephen McHattie), but that doesn’t feel like enough when the show implies that this is just one guy with an anger problem and leaves it at that.

111. Season 8, Episode 7: “Mr. Monk and the Voodoo Curse”

It seems like, for the final season of Monk, the writers just ran with every wild idea they’d pitched in previous years that was dismissed for being too silly. Some of them are silly in a fun way (see: “Mr. Monk Is Someone Else”), but this one is silly in an eye-roll-y way. Voodoo dolls seem to be predicting accidental deaths, and Natalie is convinced they’re really magic. Of course they’re not — it turns out a paramedic was planting them so she could kill her rich uncle and blame it on the dolls — but the real meat of the story is in the way Monk dismisses Natalie’s fears. The show has played with that hypocrisy before but without the vague racism that brings down this episode.

110. Season 6, Episode 10: “Mr. Monk and the Man Who Shot Santa Claus”

Christmas episodes often give television writers the opportunity to get sentimental and fanciful as the time of year makes everything seem a little more magical. It’s a missed opportunity here, though, as the premise that Monk shot (a man throwing toys off of a roof dressed as) Santa in a fit of rage never really held water. Sure, he’s a curmudgeon, but he’s not a monster. The episode doesn’t show us what actually happened on that roof, so we have to take Monk’s word for it — but why wouldn’t we? He’s Monk! There’s no tension there, so when we find out that Santa is in cahoots with some jewel thieves, it’s not especially satisfying.

109. Season 8, Episode 2: “Mr. Monk and the Foreign Man”

Monk is often very sad, but this season-eight episode takes things a bit too far when it goes out of its way to make us fall in love with the victim, watch her die in a hit-and-run, and meet her grieving husband, Samuel (Adewale Akinnuoye-Agbaje) all in the span of about two minutes. Monk, naturally, sees a lot of himself in this man whose wife was senselessly murdered, but their relationship is undermined by a weird extended bit where Monk makes Samuel, who is visiting from Nigeria, think that his eccentricities are just how things are done in America. The show is typically great at balancing its tone, but this one was a swing and a miss.

108. Season 3, Episode 9: “Mr. Monk Takes His Medicine”

The instinct to explore what Mr. Monk would look like without his phobias and compulsions is a good one, but this episode is a bit too heavy-handed in its approach. Monk finally agrees to take medication for his OCD after he accidentally lets a suspect who shot Stottlemeyer run past him. Tony Shalhoub is very funny as a newly relaxed (and obnoxious) Monk, and sells the disappointment when he realizes no one likes the new him — including his memories of Trudy. But it’s not worth the implication that psychiatric medications change your personality for the worse, and the writers do a much better job of altering Monk’s personality to comedic effect later on. (See: “Mr. Monk Gets Hypnotized.”)

107. Season 8, Episode 8: “Mr. Monk Goes to Group Therapy”

Monk has a lot of fun with putting its hero up against people who are just like him — and showing us how much he fucking hates it. The show’s writers frequently explore that dynamic in Monk’s relationship with his nemesis, Harold Krenshaw (Tim Bagley), so this episode in which Monk has to join a therapy group since his insurance company is putting a lifetime cap on his sessions doesn’t really tread new ground. It mostly serves to wrap up his rivalry with Harold, who selflessly agrees to find a new therapist so that Monk can have the group therapy sessions to himself. (The rest of the group members were all murdered by a fellow patient. It’s a whole thing.)

106. Season 7, Episode 9: “Mr. Monk and the Miracle”

Another Christmas episode that tries for holiday magic but just kind of fizzles, “Mr. Monk and the Miracle” does have the distinction of being the only episode where we see Captain Stottlemeyer without his mustache. The captain is suffering from an injured back and his medication isn’t working, but he starts to feel better when he drinks from a fountain at a local monastery. Here we learn that Leland originally wanted to be a priest, and he quits the police force to become a monk and pursue spiritual healing. Sure, the monk/Monk wordplay is fun, but that’s a lot of character development to cram into one episode. It comes as a relief when we learn that Stottlemeyer’s pharmacist was giving him placebos before he drank from the fountain, in order to prevent it from being dug up and revealing the body of a partner he killed years earlier. We’re not, in fact, losing Stottlemeyer to the Lord, and Monk’s perception of the world remains unchallenged.

105. Season 4, Episode 8: “Mr. Monk and Little Monk”

We hear some depressing anecdotes about Monk’s childhood throughout the series, but this episode is the first one where we actually get to see it. When a childhood crush, Sherry (Donna Bullock), comes to him for help solving her housekeeper’s murder, Monk is transported right back to junior high, with all its attendant angst. In flashbacks, we see little Monk prove that Sherry didn’t steal the school’s bake-sale money, intercut between grown-up Monk figuring out that Sherry’s ex-husband hired some guys to deface a painting in her house, which the housekeeper interrupted. It was all a ploy to get her to visit an art restorer (Brett Cullen), her own middle-school crush all grown up, so that they’d get together and he wouldn’t have to pay alimony anymore. It’s kind of a neat mystery, but the flashbacks drag on a little long and cut the main story’s momentum. Middle school was hard enough for all of us, we don’t need to relive it!

104. Season 8, Episode 1: “Mr. Monk’s Favorite Show”

If the flashbacks in “Mr. Monk and Little Monk” overstayed their welcome, the season-eight opener’s gimmick strikes a better balance. We get a scene of Mr. Monk (in a dream sequence) inserting himself into his favorite show, The Cooper Clan, casting himself as the cool older brother who can do no wrong. Too bad that the long road to get there is a slog. Monk is hired as the body guard for Cooper Clan actress Christine Rapp (Elizabeth Perkins) after she starts receiving death threats while promoting a new tell-all book. Monk is soon disillusioned with Rapp when he reads her book, and eventually figures out that she’s also a murderer — she’s been sending the death threats to herself so that she can kill a fan named Victor who had previously helped her rig an awards-show vote that revitalized her career.

Monk’s writers usually excel at this kind of self-referential Hollywood meta-humor, so it’s perplexing that this episode is otherwise a bit of a whiff. It’s dull up until the Cooper Clan dream sequence, with a healthy sprinkling of slut-shaming thrown in for good measure. Elizabeth Perkins is fabulous as the boozy, washed-up child actress, though.

103. Season 6, Episode 8: “Mr. Monk and the Wrong Man”

Monk occasionally plays with the idea that Monk’s wild theorizing would be untenable in the real world, but it’s kind of a cop-out here, because he’s not actually wrong. Monk feels guilty when a man named Max Barton (Tim DeZarn), who was convicted of murder on evidence Monk provided, is exonerated by DNA. There are a few funny scenes as Monk tries to help Barton rebuild his life, including when he interrupts his ex-wife’s wedding to a new man and begs him to take Barton back, only to interrupt their wedding when he figures out that Barton actually did commit the murder. He just had an accomplice, and that’s whose DNA was found.

102. Season 7, Episode 16: “Mr Monk Fights City Hall”

By season seven we’re in a bit of a holding pattern with Trudy until Monk finally solves his wife’s murder in the series finale. So this episode just kind of feels like Monk spinning its wheels. It’s an enjoyable ride, though, as Monk tries to keep the parking garage where Trudy died from being demolished in case there’s still evidence to be uncovered. When Eileen Hill (Tamlyn Tomita), the city councilwoman who was going to vote to preserve the garage, is found dead, Monk scrambles to both solve her murder and get the remaining city council members on his side. Unfortunately for Monk, that includes the councilman Harold Krenshaw. By the end of the episode Monk is no closer to solving Trudy’s murder, but he does figure out that Eileen was killed by her boyfriend when she (falsely) told him she was pregnant, and while the garage is demolished, the park that replaces it is dubbed “The Trudy Monk Memorial Playground.” Sweet!

101. Season 2, Episode 2: “Mr. Monk Goes to Mexico”

Here’s another episode where Monk is largely separated from Stottlemeyer and Disher when he’s called to Mexico to investigate a seemingly impossible death — a kid from San Francisco died in a skydiving accident … by drowning — but their absence is less egregious here as they’re replaced by some very funny counterparts. Beloved Mexican actor Tony Plana is a delight as Captain Alameda, who also has a distinctive mustache and gets exasperated with his lieutenant Plato (David Noroña). (In case the joke isn’t clear, plato is Spanish for plate … or dish.) The mystery is also pretty clever. The medical examiner who determined that the boy drowned midair was a fugitive. Monk’s testimony helped convict him of insurance fraud in the U.S., so he concocted the impossible case to lure Monk to Mexico, where he planned to kill him in revenge. Unfortunately, though, this episode is ranked so low due to some pretty racist Mexican stereotypes that are super unnecessary and make this one a bummer on re-watch.

100. Season 8, Episode 12: “Mr. Monk Goes Camping”

As one of the final few episodes in the series, “Mr. Monk Goes Camping” has a lot of heavy lifting to do, plot-wise. It has to be a fun murder-of-the-week mystery, while also setting up Monk’s reinstatement in the next episode. (See: “Mr. Monk and the Badge.”) It’s successful on the latter front, with a young Alex Wolff starring as the son of Frank Willis, an officer on Monk’s review board who still had reservations about reinstating him to the force. Monk joins Randy on a camping trip with a group of boys including the young Willis, whom he wants to win over. It’s admittedly pretty funny to watch Monk try to make a good impression while surrounded by everything he hates. But the concurrent story line about a pair of bank robbers trying to recover some shotgun shells they left around the campsite falls flat. It’s essentially a retread of Man of the House starring Chevy Chase and Jonathan Taylor Thomas, which is not a compliment.

99. Season 2, Episode 9: “Mr. Monk and the 12th Man”

When a string of bizarre homicides with seemingly random victims sweeps San Francisco, Monk notes that they’re a little too random: He suggests that they were all on a jury together. It’s a pretty by-the-book episode, with Monk eventually deducing that the defendant in the case was killing off jurors because one of them was blackmailing him but he didn’t know which one. There’s a fun subplot with Sharona dating the deputy mayor, who’s kind of a jerk, but she keeps dating him because she’s getting attention. But there’s a character here — a handyman who has a piece of pipe stuck in his head and keeps yelling non sequiturs and thinking he hears the phone ring — that just feels too stupid. I say this with affection as a lover of stupid things, but it doesn’t quite feel like Monk’s sense of humor.

98. Season 2, Episode 5: “Mr. Monk and the Very, Very Old Man”

It’s a recurring joke in this episode that Captain Stottlemeyer’s wife, Karen (Glenne Headly), made a boring documentary about a really old guy that the captain has a hard time sitting through. Unfortunately the episode isn’t much more interesting. It’s mostly notable as the first real glimpse we get of Leland’s marriage, and it’s a pretty grim one. Glenne Headly is always a treasure, though.

97. Season 7, Episode 5: “Mr. Monk Is Underwater”

Natalie and Monk initially bond over their shared widowhood — Natalie’s husband, Mitch, was a navy pilot killed in action — but we don’t get too much of his backstory until the middle of season seven. Mitch’s friend Lieutenant Steven Albright (Casper Van Dien) looks Natalie up and they share a palpable romantic tension, but he admits that he’s actually there to ask for Monk’s help proving that a fellow officer’s suicide was actually murder. He invites Monk to come aboard his boat to check it out but doesn’t tell him that it’s a submarine. Monk’s claustrophobia keeps him on edge while onboard; he hallucinates Dr. Bell to cope, and people have to keep asking him to repeat what he imagined Dr. Bell saying. But the mystery is kind of lame and the submarine journey is bookended with some truly awful CGI backgrounds when the gang finally disembarks. They couldn’t have found a dock to shoot at for a day instead of this technology that was (literally) not ready for prime time?

96. Season 7, Episode 14: “Mr Monk and the Bully”

The other Monk flashback episode is superior to “Mr. Monk and Little Monk,” both because it uses the flashbacks more sparingly and because the present-day conflict is more interesting. This time it’s Monk’s middle-school bully, Roderick (Noah Emmerich), who is now a successful businessman and needs his help investigating his new wife, Marilyn (Julie Bowen), who he suspects of having an affair. Monk doesn’t usually take on this kind of domestic case, but he revels in the opportunity to hurt Roderick. The resolution is a classic whodunnit twist: Marilyn has an identical twin named Patrice. The sisters were adopted as infants, and when Patrice learned that she had a twin married to a millionaire, she decided to kill them both and take the money. It’s so ridiculous I have to applaud the moxie, even if the resolution doesn’t quite feel earned.

95. Season 8, Episode 4: “Mr. Monk Is Someone Else”

Here’s the silly season-eight episode that I have the most affection for, even if it’s too much of a mess to be ranked any higher. It’s another doppelgänger episode, but this time it’s Monk with the double — who happens to be a high-end hitman named Frank DePalma. The opening of the episode is genuinely very funny, as we see (what appears to be) Mr. Monk get hit by a bus as he walks across the street. (I don’t know why it’s always funny to see someone hit by a bus!) The jokes keep coming as Monk is asked to go undercover as DePalma, who was actually run over, and we get to see Tony Shalhoub’s mobster persona, as translated through a very nervous Mr. Monk. But the episode loses points in comparison, as it’s the second mob-related episode in the show’s run. While this one has The Sopranos’ Vincent Curatola and Louis Lombardi as guest stars for a fun, meta nod to the gangster genre, “Mr. Monk and the Godfather” has Philip Baker Hall. There’s just no beating that.

94. Season 5, Episode 2: “Mr. Monk and the Garbage Strike”

For a show written by television writers (as many television shows are), Monk has some unfortunate portrayals of unions as corrupt and violent. “Mr. Monk and the Garbage Strike” is one such episode — though not the most egregious example (see: “Mr. Monk and the Captain’s Wife”). It’s a shame, because the rest of the episode is a lot of fun, with Mr. Monk spiraling when a strike by San Francisco’s sanitation workers leaves the streets full of garbage. The union suspends negotiations with the city when their leader is found dead, and Monk is so discombobulated about being surrounded by trash that he starts throwing out random theories, including that Alice Cooper murdered the boss for his wingback chair. (Cooper cameos in the reenactment, which is just delightful.)

93. Season 6, Episode 5: “Mr. Monk and the Birds and the Bees”

With apologies to Emmy Clarke, I just don’t care enough about Julie to be invested in her high-school romance. The mystery hinges on a boy manipulating Julie to break up with her boyfriend so that she’ll stop wearing a T-shirt with a photo of their faces on it, because in the background you can see the episode’s bad guy meeting with the man he hired to break into his house so he could get away with killing his wife. There is one funny scene where Monk has “the talk” with Julie, but otherwise it’s not as moving as the writers wanted it to be.

92. Season 6, Episode 13: “Mr. Monk and the Three Julies”

This has the same Julie problem as “Mr. Monk and the Birds and the Bees” but edges it out for two reasons. One is that the stakes are much higher, as there appears to be a murderer on the loose killing women named Julie Teeger. Natalie, naturally, panics. Which leads us to the second reason for this episode’s slightly higher ranking: an extended bit where Natalie hears about a dead Julie Teeger and hijacks the captain’s brand-new car to rush to the crime scene. She smashes up the car in her haste, and Stottlemeyer grudgingly reassures her that any parent would do the same. And then it happens again. Ted Levine sells the mix of understanding and exasperation so well, it’s hard to believe this is the same guy who once said, “It rubs the lotion on its skin or else it gets the hose again.”

91. Season 1, Episodes 1 and 2: “Mr. Monk and the Candidate”

The two-part Monk pilot is kind of like watching a TV movie that was later turned into a series. It doesn’t look quite right, the pacing is a little slower, and the tone a little drier, and the characters aren’t fully formed yet. Captain Stottlemeyer doesn’t even like Monk! But it does a great job of setting up the type of detective show it’s going to be, introducing Monk’s OCD as “a gift … and a curse.” He notices things no one else does but also lets a perpetrator get away because he’s afraid of heights. Then he’s able to overcome his fears, briefly, when Sharona is in danger. We also learn the stakes of Trudy’s unsolved murder and the potential for Monk to be reinstated. It was good enough to get picked up for a series order, and that’s all that really matters!

90. Season 6, Episode 4: “Mr. Monk and the Bad Girlfriend”

Captain Stottlemeyer’s love life has always been a disaster — his marriage to Karen ends in season four — so it was only a matter of time before things went south with his new girlfriend, Linda Fusco (Sharon Lawrence). Because this is Monk, naturally she turns out to be a murderer. The episode is notable more for how it tests the relationship between Stottlemeyer and Monk, though, as the captain refuses to believe that Linda killed her real estate partner and is furious at Monk for suggesting as much. Whether Leland can forgive Monk for accusing his girlfriend of murder is the episode’s main source of tension, since it’s pretty clear she did it from the moment the title pops up in the opening credits. A very bad girlfriend indeed.

89. Season 8, Episode 3: “Mr. Monk and the UFO”

Okay, now we’re just being silly. Mr. Monk thinks he sees a flying saucer when Natalie’s car breaks down in the Nevada desert. Naturally, UFO enthusiasts flock to the site and begin to think Monk is an extraterrestrial himself. It’s an absolutely unhinged episode, and while it stretches credulity that Natalie would actually think Monk is an alien, I’m not mad at it. It’s fun!

88. Season 5, Episode 13: “Mr. Monk Is on the Air”

Monk’s writers often make in-jokes about Hollywood, and occasionally parody real-life figures. This episode does both, to mixed results. Howard Stern–esque shock jock Max Hudson’s wife dies from a gas leak while he’s on the air. Her sister is convinced Hudson killed her, though, and enlists Monk’s help to solve it. Steven Weber turns in a great performance as Hudson, who needles and bullies Monk so badly that it’s immensely satisfying when the tables are turned and Monk nails him for his wife’s murder. The main knock against this episode is that the jokes about the radio industry don’t feel as specific and grounded as the jokes about the television industry in episodes like “Mr. Monk and the TV Star,” which makes sense, given that the show is written by people in the television industry.

87. Season 3, Episode 8: “Mr. Monk and the Game Show”

Whenever John Michael Higgins shows up you know you’re in for a good time. Here he guest stars as an unscrupulous game-show host who’s helping a contestant cheat and who murdered a production assistant who found out their scam. But this episode’s main purpose is to give us more of Trudy’s backstory. Her dad, Dwight (Bob Gunton), is the show’s producer, and he’s the one who asks Monk to figure out how they’re cheating. We get flashbacks to Adrian meeting Trudy’s parents for the first time, and it’s very sweet to see the bond between these two men united in grief.

86. Season 6, Episode 14: “Mr. Monk Paints His Masterpiece”

For all of his self-hatred, Monk does have a chip on his shoulder about being perceived as the best at what he does. “Mr. Monk and the Other Detective” is a better exploration of Monk’s ego, but this season-six episode takes another stab at it. Monk begins to think he’s an artistic genius when he starts painting as a creative outlet, and an eccentric collector (a perfectly cast Peter Stormare) keeps buying up his work. It’s fun to watch everyone around Monk start to flatter him, only to be relieved when they find out the collector is a Russian mobster and the canvases are made of counterfeit money. A pretty good Monk episode that’s also a commentary on the subjectivity of art? Now that’s art.

85. Season 7, Episode 12: “Mr. Monk and the Lady Next Door”

A solid contender for second-funniest cold open (after the bus crash in “Mr. Monk Is Someone Else”), this episode begins in a Guinness World Records museum where a security guard is pushed over a railing and impaled on a swordfish. But the real meat of the episode is a new relationship Monk strikes up with his neighbor, Marge. Played by special guest star Gena Rowlands, Marge has the kind of sweet, maternal vibe that Monk never got from his own mother, but he self-sabotages when he starts to think she must have an ulterior motive for hanging out with him and accuses her of being the murderer’s mom trying to steer him away from solving the case. The goofy set pieces (a competitive egg-eater factors into the mystery) juxtaposed with deep sadness is quintessentially Monk, even if the balance is a little off here.

84. Season 1, Episode 4: “Mr. Monk Meets Dale the Whale”

This is a tough one. It’s our first introduction to Monk’s Moriarty; the show is at its best when Mr. Monk faces off against a powerful foe who gets under his skin, and there’s no more powerful foe than Dale “the Whale” Biederbeck. (It’s Adam Arkin here, but he’s recast every time we see him.) But there’s our problem. The villain is a grotesque caricature of a fat person, and it’s extremely hard to watch all our heroes be as disgusted by his body as they are by his horrific actions. Without the fatphobia, this would be a top-ten episode. As it stands, it’s hard to get through.

83. Season 7, Episode 15: “Mr. Monk and the Magician”

Tony Shalhoub’s performance may be the heart of Monk, but the show’s eccentric recurring characters are its lifeblood. One of my favorites is Kevin Dorfman (Jarrad Paul), Monk’s upstairs neighbor who never stops talking. His first appearance in “Mr. Monk and the Paperboy” is the quintessential Kevin episode, but this is his swan song. Tragically, Kevin is murdered in “Mr. Monk and the Magician” by (who else?) a magician (played by real-life magician Steve Valentine). Watching Monk avenge his pal is a lovely full-circle moment for their friendship; Kevin drove Monk crazy most of the time, but this episode proves he really did love him.

82. Season 5, Episode 16: “Mr. Monk Goes to the Hospital”

This season-five finale is probably the most high-stakes example of Monk’s “gift” becoming a “curse” and vice versa. He makes Natalie take him to the emergency room for a bloody nose but ends up discovering that a doctor killed his colleague and framed a patient for it. Monk, naturally, starts looking into it, so to get Monk out of the way, the doctor admits him to the hospital and attempts to poison him with a medication he’s allergic to. This episode loses points for being a rehash of the killer doctor story in “Mr. Monk and the Asylum,” and it’s not the most exciting season finale in the show’s history, but it’s still fun to see Monk validate his own paranoia.

81. Season 6, Episode 3: “Mr. Monk and the Naked Man”

This episode is good for two reasons: Diedrich Bader and Alfred Molina. The former guest stars as a nudist named Chance Singer who’s a thorn in the side of the latter, a billionaire named Peter Magneri who wishes the view from his beach house featured fewer naked people. When a woman turns up murdered outside of Singer’s trailer, Monk is convinced the nudist killed her, with little evidence other than the fact that he hates nudity. Singer points the finger at Magneri, as the woman was trying frantically to get into his beach house on the night she was murdered. It turns out neither of them did it — it was the woman’s roommate, an X-ray technician who knew Magneri was seriously ill and started short-selling his company; she killed her roommate when she found out and planned to tell him — but their petty sniping is fun to watch in the meantime.

80. Season 7, Episode 13: “Mr. Monk Makes the Playoffs”

If Monk is weakest when its titular character is separated from the people who keep him grounded, this episode in which Monk is forced to spend some one-on-one time with the captain is the tonic. It’s not an especially great mystery — a pro football player’s chauffeur steals his playbook to sell to the other team, then kills him when he finds out — but the mutual reluctance between Adrian and Leland to hang out without a buffer is a great little exploration of their relationship. Also, Bob Costas plays himself as a good friend of Monk’s, which is just a great cameo.

79. Season 7, Episode 4: “Mr. Monk Takes a Punch”

Monk has a few homage-y episodes, which work best when they highlight an interesting parallel or new facet of Monk’s personality, but we’re scraping the bottom of the barrel by the time we get to season seven’s ode to Rocky. What’s the connection to Monk, other than the fact that the writers really like Rocky? (As does everyone with a heart.) Still, the montages of the episode’s imperiled boxer (James Lesure) helping Monk train for a physical are so funny and sweet, they almost make up for the fact that the Rocky of it all doesn’t make much sense.

78. Season 1, Episode 3: “Mr. Monk and the Psychic”

Early episodes of Monk lean into his curmudgeonly tendencies, including this one — the first episode to air after the pilot — where Monk is frustrated that a psychic named Dolly (Linda Kash) seems to help the cops locate a body. Unable to accept that such a thing is possible, Monk sets out to prove that she’s lying. She’s not lying … but she’s also not psychic. A man who killed his wife by causing her car to go flying off the road had to recover the body after a mudslide and drove a sleeping Dolly to the scene. This episode does a lot of good work in establishing Monk’s frustration with bad cops — the murderer is the former SFPD commissioner — and his willingness to confront powerful men in the pursuit of justice. But the supernaturalness of it all kind of muddles the mystery.

77. Season 8, Episode 11: “Mr. Monk and the Dog”

Okay, obviously it’s adorable to see Monk interacting with a dog. He’s a very lonely man, and so when Natalie insists that he take in a murdered woman’s dog, it is of course delightful to watch him slowly open his heart to Shelby (the dog) and protect her when she gives birth to puppies (that turn out to be solid evidence in the woman’s murder). And yet! This episode comes after “Mr. Monk and the Kid,” one of the show’s best, and just seems like a watered-down version of that story line. Plus, Natalie’s extended family is supposed to be extremely wealthy, and a family reunion in the park with matching T-shirts is not a rich-people activity. Maybe if they promised a poor kid a million dollars if he made a home run …

76. Season 6, Episode 12: “Mr. Monk Goes to the Bank”

There are a handful of standout Randy episodes over the show’s run, including this season-six highlight. The writers have a lot of fun with our trusty lieutenant being so insecure about people taking him seriously that he inadvertently turns himself into a joke. That happens here when a living statue ignores Randy’s questioning, so Randy tries to prove he could do a better job standing still for long periods of time. It’s only fitting that Randy’s ongoing rivalry with the street performer is what saves his life, along with Monk, Natalie, and Stottlemeyer, who’ve been locked in a vault after figuring out that the bank’s entire staff planned a robbery.

75. Season 4, Episode 9: “Mr. Monk and the Secret Santa”

If “Mr. Monk and the Miracle” and “Mr. Monk and the Man Who Shot Santa Claus” suffer from reaching for implausible premises, the season-four Christmas episode aims right down the middle with a killer Secret Santa. Fun! A cop is killed by a poisoned wine meant for Stottlemeyer, who immediately thinks he knows who tried to kill him — the brother of a bank robber whom Stottlemeyer killed while arresting him. But in between Christmas-y high jinks, including acting as a mall Santa to try to extract info from the suspect’s daughter, Monk figures out that the poison was never meant for Stottlemeyer. It’s a little queasy to see our favorite captain so zealously pursue an innocent man, but the fact that he’s proved wrong is a Christmas miracle.

74. Season 5, Episode 14: “Mr. Monk Visits a Farm”

Brooke Adams, Tony Shalhoub’s wife, appears here as her third Monk character … and the first one that actually likes Mr. Monk. That real-life connection is sweet, but this is Randy’s episode. He quits the force after making a major mistake that almost ruins a case, going to become a farmer on the ranch his uncle left him after dying in an apparent suicide. A few days later, though, Randy calls Monk to investigate the death, which Randy thinks is suspicious. The farm life clearly doesn’t sit well with Monk, which gives us some funny scenes (including one in which Mr. Monk thinks he’s accidentally gotten high), but it’s Randy’s investigation that provides the best jokes. Mirroring Mr. Monk’s standard line, “Unless I’m wrong, which, you know, I’m not,” Randy presents his theory with, “Unless I’m wrong, which I probably am.” Monk even lets him believe that he solved the case himself, which is just the confidence boost Randy needs to return to the force.

73. Season 7, Episode 11: “Mr. Monk on Wheels”

Bradley Whitford is perfectly cast in this episode as Dean Berry, a crunchy biotech CEO whose bike is stolen from outside his lab. But his case takes a backseat to Natalie’s relationship with Monk, which is strained nearly to its breaking point. Monk is shot in the leg while pursuing the suspect who stole the bike, which Natalie insisted on investigating. Natalie feels intense guilt for inadvertently getting Monk hurt and nearly kills herself caring for him. He’s being a real dick to her, showing us an ugly side of his personality that gets a little hard to watch. Ultimately, though, he sees how cruel he’s being, and apologizes to Natalie before solving the case. The episode ends on a perfect button when Natalie accidentally shoots Monk in the other leg while pursuing the bad guy (Berry’s assistant, played by Pamela Adlon). At least now they’re even!

72. Season 1, Episode 11: “Mr. Monk and the Earthquake”

Because many Monk writers are comedy guys, they frequently get fellow comedy guys to guest star. Case in point: Amy Sedaris, who’s an absolute joy as Sharona’s younger sister, Gail. This episode introduces her character, who is shown to be competitive with Sharona — from accusing her of following her to San Francisco (Sharona insists Gail begged her to move here) to flirting with Randy (who has an obvious crush on Sharona). This isn’t Gail’s best episode (see: “Mr. Monk Goes to the Theater”), but it establishes her as a major figure in Sharona’s life, fleshing out her character and explaining what a woman with such a strong New Jersey accent is doing on the West Coast.

71. Season 2, Episode 16: “Mr. Monk Goes to Jail”

Our second run-in with Dale the Whale (played here by Tim Curry) bogs down what is otherwise a really fun season finale. The first time we see Monk go undercover, he poses as a new transfer to a local prison when a death-row inmate is poised right before he was scheduled to be executed. He apparently owed money to Dale, which makes him the prime suspect, but he swears he’s not the culprit — and will give Monk information on Trudy’s death if he can prove otherwise. Monk gets a tip about a dangerous inmate named Spyder Rudner (Danny Trejo), but that’s a dead end as well. By the time Monk figures out that the prison’s librarian is the bad guy, he’s made friends with Rudner, just in time for Rudner to save him from a Nazi gang that the librarian sent to take him out.

70. Season 3, Episode 4: “Mr. Monk Gets Fired”

Monk typically doesn’t get too gruesome in the way a procedural such as, say, Criminal Minds does. This episode is the closest Monk gets to that grittier tone, with some chainsaw-induced blood splatter and a detailed description of a torso found in the San Francisco Bay. (There’s also a close-up of a kid coughing, which is also gross, just in a different way.) That grimness is exacerbated by the overarching subplot about a new police commissioner (Saverio Guerra) who fires Monk and the depression that Monk falls into after losing the thing that gives his life meaning. The darkness is punctuated by a satisfying conclusion, though, as Monk solves the case of the recovered torso by matching its DNA to a toupee worn by the commissioner, which Sharona rips off his head when he refuses to admit he’s wearing a piece. Not to worry — this is still a very silly show.

69. Season 1, Episode 9: “Mr. Monk and the Marathon Man”

In season one the writers are still experimenting with figuring out Monk’s background, and this episode takes a fun swing at establishing him as a former track star who quit after he lost a race because he was fixing his uneven shoelaces. He’s so obsessed with running, in fact, that he’s pumped to see his hero, professional marathoner Tonday Mawwaka (Zakes Mokae) participating in the San Francisco marathon — that is until Mawwaka allegedly helps a fellow marathoner kill his mistress during the race. Of course, Monk figures out that he’s innocent, and Mawwaka gives Monk a pair of shoes and encourages him to start running again. The only negative is a weird subplot where the marathon workers keep thinking Monk is being racist in a series of misunderstandings. It’s not, like, offensive, it’s just not very funny.

68. Season 3, Episode 7: “Mr. Monk and the Employee of the Month”

We hear snippets of information about Monk’s time on the force in the first few seasons, but this episode does a lot of background dumping when we’re introduced to his former SFPD partner, Joe Christie (Enrico Colantoni). Christie, now working as a security guard for a Megamart superstore, suspects that an employee was murdered, but Monk initially doesn’t want anything to do with him. We learn that soon after Trudy’s death, Christie was discharged when a brick of cocaine went missing from a case he worked. Monk reluctantly agrees to help, though, and it’s touching to see him warm to his old friend. Once they solve the Megamart case, Monk even helps figure out what happened to the drugs and clears Christie’s name. It’s a shame that we never see Christie again, most likely because Enrico Colantoni was too busy on Veronica Mars. (In a fun crossover nod, his character gives a fake name of “Adrian Monk” in a later Veronica Mars episode.)

67. Season 1, Episode 8: “Mr. Monk and the Other Woman”

The first time we see Monk start to have feelings for another woman sends him spiraling in this season-one episode. A woman (who looks remarkably like Trudy) needs his help when she’s accused of murdering her neighbor and his lawyer over a property line dispute. It’s pretty shocking — in a good way! — to see Monk on a date, but the surrounding mystery is less interesting than the romantic tension, which will be explored more thoroughly in later episodes. (See: “Mr Monk Falls in Love” and “Mr. Monk and the Blackout.”)

66. Season 2, Episode 14: “Mr. Monk and the Captain’s Wife”

The second strangely anti-union episode is more forgivable because the union boss doesn’t actually turn out to be involved in this one — it’s all collateral damage from an unrelated criminal named Evan Coker (Daniel Goddard), who needed to recover evidence from his car that was being towed by a scab driver. But the emotional core of the episode is Leland’s relationship with his wife, as indicated by the title. When Coker shot the tow truck driver, it caused an accident that left Karen in a coma, which sends the captain into a hole of rage and grief. We get plenty of glimpses of the hurting heart behind Leland’s gruff exterior, but in this episode it’s completely exposed.

65. Season 4, Episode 12: “Mr. Monk and the Captain’s Marriage”

And here’s where Leland’s heart finally breaks. While checking out a crime scene, the captain punches a cop named Ryan Sharkey (Nicky Katt) for making innuendo that he’s having an affair with Karen. Stottlemeyer is sent to anger management classes and asks Monk to follow Karen to see if she is indeed having an affair. He tracks her to a restaurant where she’s having lunch with a man, but the classes actually worked. Leland tells Karen he forgives her and they can work through her infidelity. But she reveals that she wasn’t meeting Sharkey — she was meeting a divorce lawyer. Sharkey was the murderer, and just picked a fight with Stottlemeyer so his DNA would be at the scene.

64. Season 3, Episode 10: “Mr. Monk and the Red Herring”

Natalie’s first episode comes midway through season three, after Bitty Schram, who played Sharona, left abruptly, reportedly over a contract dispute. Natalie first shows up as an accidental killer — she stabs an intruder whom she found trying to steal Julie’s fish in the middle of the night. She asks Monk to help figure out why someone would want to steal an ordinary pet fish, but he’s been having a hard time since Sharona moved away. (In the fiction of the show, she got back with her ex-husband and moved to New Jersey with him and Benjy.) The title of the episode is a pun, though, as the guy was not after the fish but the “fake” moon rock in the tank, which turned out to be real and worth a ton of money.

That’s a really clever premise for a mystery, and the episode does a good job of introducing Natalie as a capable replacement for Sharona in Monk’s life, but the writers are still figuring out her character. Here she’s just kind of mimicking Sharona’s brash personality. We’ll eventually come to love Natalie for who she is in her own right, but at this point it’s just highlighting how much we miss Sharona.

63. Season 5, Episode 3: “Mr. Monk and the Big Game”

Obviously I am biased, but the joke in this episode about Julie having two friends named Emily gets me every time. Still, it’s otherwise a solid episode, with Julie and the Emilys asking Monk to investigate the death of their beloved basketball coach, which was ruled an accident. In the meantime, Natalie steps in as coach of the basketball team, with Monk reluctantly joining as her assistant coach. Because this is Monk, there’s a sad little subplot about how he never won a trophy despite his mother cleaning off the mantle to make room for some, and the episode ends with Natalie and Julie presenting Monk with 100 trophies representing all the cases he solved. (This sets up a continuity error for “Mr. Monk’s 100th Case” in season seven, though, which would drive Monk crazy.)

62. Season 5, Episode 5: “Mr. Monk, Private Eye”

Let this be a lesson to all of us: Never break up with someone when you’re alone on a boat with them! This episode opens on a doctor named Jay Bennett (Frederick Weller) killing his mistress and dropping her in the bay. We don’t check back in on the murder until later, though. First, Natalie convinces Monk to open a private detective agency since work from the police department has been scarce. He’s hired by Linda Fusco, in her first appearance, to investigate who dinged her car, which Monk feels is beneath him. Turns out, though, it’s none other than Dr. Jay Bennett. It’s an enjoyable little episode overall, but it feels like a missed opportunity for more nods to classic hard-boiled detective stories.

61. Season 7, Episode 6: “Mr. Monk Falls in Love”

This episode loses points for retreading a story line we’ve seen before, with Monk developing feelings for a woman who isn’t Trudy (see:“Mr. Monk and the Other Woman”), but gains points for doing a better job of it. This mystery is easier to follow since the woman, Leyla (Joanna Pacula), is a suspect immediately. It also makes the tension more straightforward, with Monk refusing to believe that Leyla is a murderer, despite all evidence to the contrary, including Leyla admitting to the crime. He finally figures out that her mother was the real culprit, and that her victim was a war criminal who butchered her people in the fictional country of Zemenia. Leyla was just trying to protect her mom by confessing. Unfortunately for Adrian, most relationships would have a hard time bouncing back from accusing their mom of murder, and Leyla tells Adrian to go back to his life/wife.

60. Season 6, Episode 9: “Mr. Monk Is Up All Night”

Another episode where Monk becomes obsessed with a woman, though this time it’s not explicitly romantic. “Mr. Monk Is Up All Night” has an enticing noir-y vibe, a style that was admittedly executed better in the season-five episode “Mr. Monk and the Leper.” Monk can’t sleep because he can’t stop thinking about a woman he passed on the street and witnesses a murder while wandering around late at night. It turns out that the woman had a cornea transplant — she has Trudy’s eyes. Sure. This episode does get bonus points for my favorite character actor, Donal Logue, who steals the show in a single scene as a grifter who bets he can guess where Monk got his shoes. (The answer: “You got your shoes … on your feet.”)

59. Season 3, Episode 11: “Mr. Monk and the Cobra”

One of the better homage episodes, “Mr. Monk and the Cobra” is a love letter to kung fu movies, highlighting the monklike discipline (pun very much intended, obviously) that Monk follows in his own life. It’s elevated by the late actor Mako, who guest stars here as a teacher whose student, martial artist and movie star Sonny Chow, seems to have come back from the dead. The biggest bummer of the episode is the stinginess Monk shows toward Natalie, who’s still getting to know her new boss, in refusing to pay her expenses. Monk’s miserly tendencies are one of the uglier aspects of his personality, and it doesn’t always read as the quirky eccentricity it’s presented as.

58. Season 7, Episode 3: “Mr. Monk Gets Lotto Fever”

We’ve already touched on Monk’s inflated ego in “Mr. Monk Paints His Masterpiece,” but this episode reveals that Natalie’s ego is just as easily puffed up. She’s asked to present the lottery numbers on TV when the previous lotto girl is found murdered and starts acting like a bit of a diva. Natalie’s attitude drives Monk crazy since she’s getting more attention than he is, but it doubles as the catalyst for Monk solving the case. Natalie gets the sound operator fired when she chides him for leaving cords on the ground, but he had rigged the lottery balls by covering certain numbers in metallic paint and hiding a magnet in the mics. He murdered the actress who found out about the scheme and then framed Natalie for the cheating. It’s a neat little mystery, made more satisfying by the Natalie and Adrian role reversal.

57. Season 8, Episode 10: “Mr. Monk and Sharona”

Natalie was Monk’s assistant for longer than Sharona, but she never quite fills the shoes of his original nurse and companion. So it’s a funny, meta moment when the two finally meet for the first time near the end of the series and butt heads over how to handle Monk’s eccentricities. It’s really good to see Sharona again, so we can forgive the somewhat boring mystery about her uncle falling on a golf course, since it’s an excuse to get her to California. Her arrival has another purpose, though. It’s close to the finale and we need to start setting up everyone’s happy ending. Randy’s is, delightfully, moving to New Jersey to be with Sharona, who he’s had a crush on for years. Awwwwww.

56. Season 3, Episode 1: “Mr. Monk Takes Manhattan”

A big part of a Monk writer’s job is figuring out how to trigger Monk’s phobias, and they got the biggest bang for their buck by dropping him into Manhattan, with all its noise and grime and people. (Greatest city on earth!!!) He’s here to track down Warrick Tennyson (Frank Collison), whom Dale the Whale told him was involved in Trudy’s death. But he’s stymied by the New York district attorney, who needs the dying Tennyson to testify in a federal racketeering case. Their NYPD liaison strikes a deal that if Monk can solve the recent murder of a Latvian ambassador, he can meet with Tennyson. He, of course, does, and the final scene with Tennyson is chilling as Monk learns that he was hired to murder Trudy by a six-fingered man and then turns off his morphine. He watches as Tennyson’s pain comes flooding back, before telling him, “This is Trudy, turning [your morphine] back on.”

55. Season 6, Episodes 15 and 16: “Mr. Monk Is on the Run,” Parts 1 and 2

The pursuit of the six-fingered man is Monk’s main goal for most of the series, which comes to a head in this season-six two-part finale when Monk thinks he’s tracked him down. It’s a ploy, though; Monk is framed for murdering the man by a small-town sheriff named Rollins (Scott Glenn) and goes on the run to clear his name. The first episode of this two-parter ends with Captain Stottlemeyer appearing to shoot the fugitive Monk, only to reveal at the beginning of the next hour that they planned the whole thing to give Monk cover to investigate. It turns out that Rollins was hired by none other than Dale the Whale. It’s a fittingly dramatic finale that gives Monk new leads to chase in Trudy’s murder, even if the two-part format makes it sag a bit in the middle.

54. Season 3, Episode 12: “Mr. Monk Gets Cabin Fever”

For as many powerful criminals as Monk crosses, it’s a wonder he doesn’t go into hiding more often. In this episode, Monk is taken into witness protection after he sees a mob hit go down. It’s a good opportunity for the writers to put him in a classic fish-out-of-water scenario, as the feds place him in a remote lakeside cabin to wait until trial. But murder follows Monk everywhere, and he soon suspects his neighbor across the lake of killing her husband. Both cases come to a head when Randy inadvertently leads the mob’s hitmen to the cabin after a fortune cookie convinces him Monk’s in danger. The fortune-cookie thing is a bit heavy-handed, but it does lead to a funny dual-summation by Randy and Monk, with the two talking over each other to explain, “Here’s what happened.”

53. Season 2, Episode 13: “Mr. Monk and the Missing Granny”

One of the few episodes where no one actually dies, “Mr. Monk and the Missing Granny” sees Monk tracking down a kidnapped elderly woman. Her law-student granddaughter, played by Rachel Dratch, says she doesn’t have enough money to pay Monk but promises to help Monk get reinstated to the police force in exchange. Dratch’s signature style of nervous comedy plays great against Monk’s own, and the solution to the crime is clever — the antique dealers who kidnapped her assumed everyone would be so relieved when she was found that they wouldn’t remember the valuable chair they stole from her house. The only sour note is the implication that Monk possibly getting his job back through ADA accommodations is taking a shortcut.

52. Season 8, Episode 5: “Mr. Monk Takes the Stand”

In the majority of Monk episodes — and police procedures generally (with the notable exception of Law & Order) — once the crime is solved, it’s over. Credits roll; the good guys won. This season-eight standout reminds us that there’s a whole legal process to sort out before the bad guy is convicted and makes the logical leap that Monk’s outlandish theories don’t hold up well in court. Jay Mohr guest stars as a wonderfully punchable defense attorney who needles Monk on the witness stand and defends the man who (allegedly!) murdered his wife. He’s acquitted, but Monk finds a way to convict him on another murder, which also resolves a sweet subplot involving Randy and a kid he mentored who was being pegged for the crime.

51. Season 1, Episode 7: “Mr. Monk and the Billionaire Mugger”

The first of Monk’s parody characters, the victim in this episode is a Bill Gates–type computer genius named Sidney Teal (J.C. MacKenzie) who is shot to death in a mugging — he was the mugger. No one can figure out why a billionaire was shaking down a guy for a few bucks, but Monk eventually connects Teal to the man who shot him, a fraternity brother who was sleeping with his wife. It’s a neat enough little mystery, with a funny subplot about the captain trying to track down the “fraidy-cop” who was seen running from the scene of the crime, but the most interesting element is in hindsight, as we see Silicon Valley’s rising impact on San Francisco when this episode aired in 2002.

50. Season 5, Episode 11: “Mr. Monk Makes a Friend”

Another pretty standard Monk episode elevated by a perfectly cast guest star, “Mr. Monk Makes a Friend” brings on Andy Richter as a man named Hal who becomes friends with Monk after running into him outside a grocery store. Natalie and the captain are suspicious that anyone who didn’t already love Monk would willingly hang out with him. Of course they’re right; Hal is just buddying up to Adrian so he can intercept his mail, which would tie him to a murder. Watching Adrian virtually become a giddy kid with a new BFF is classic Monk — an addicting blend of sad and silly — since we know he’ll be crushed when he finds out Hal doesn’t actually care about him or even like him. (Though the writers dip a toe into too-silly territory when Monk starts treating Hal like a childhood crush, asking him to be his best friend as if he’s asking him to go steady.)

49. Season 6, Episode 7: “Mr. Monk and the Daredevil”

Monk’s competitive relationship with Harold Krenshaw is well documented, so when it appears that Harold has been living a double life as a daredevil known as the Frisco Fly after falling off a building in a green morph suit, Monk spirals. He visits Harold in the hospital to try to figure out how he got over his fear of heights, but soon realizes that Harold was set up: Someone tried to kill him by dressing him up and throwing him off a roof. David Koechner guest stars as Harold’s cousin who tried to murder him so he’d inherit all of their uncle’s money. The episode kind of sags in the middle once it’s clear that Harold isn’t the Frisco Fly, but the premise is so fun that you almost don’t notice. Plus, we get the best summation of Harold and Monk’s relationship when Natalie says, “They’re good friends, they just don’t like to admit it.”

48. Season 5, Episode 7: “Mr. Monk Gets a New Shrink”

By the time season five rolls around, we all love Dr. Kroger as much as Monk does, so it’s genuinely upsetting when he announces he’s quitting. His office cleaner is murdered after hours, and Dr. Kroger blames himself since everyone assumes that a patient did the crime. Tony Shalhoub turns in one of the funniest scenes of the series when he goes through all of the stages of grief in the span of about 90 seconds … only to cycle right back around to denial as soon as he reaches acceptance. Naturally Monk solves the case — the murderer wasn’t a patient after all, it was a drug dealer who worked in the same office park — and we blessedly get another season and a half of Dr. Kroger’s wisdom.

47. Season 5, Episode 12: “Mr. Monk Is at Your Service”

This is a really fun example of Monk’s Columbo-style episodes in which we know who the killer is from the beginning, so the main narrative tension comes from wondering how Monk is going to catch them. That allows guest stars to really lean into their villainy, since they don’t have to maintain the mystery of who the bad guy is. Sean Astin takes on that role here, and commits hard as an obnoxious rich guy who killed his father and stepmother, stealing the inheritance from his stepsisters. He’s also been carrying a torch for Natalie since childhood (we learn in “Mr. Monk Goes to a Wedding” that her family is extremely wealthy) and is perfectly smarmy as he tries to woo her.

46. Season 7, Episode 2: “Mr. Monk and the Genius”

Monk’s brilliance is most effective when it’s squared up against an equally brilliant (evil) mind, like Sherlock and Moriarty. In this episode, that metaphorical chess match becomes literal. The villain is a chess master, Patrick Kloster (David Strathairn), whose wife dies of an apparent heart attack while he’s at a tournament miles away. Monk knows Kloster did it, though, because his wife hired Monk to solve her murder days earlier. Kloster had been taunting her, telling her he was going to kill her soon. Monk figures out how he did it by studying Kloster’s favorite chess move — the poison pawn — and deduces that he poisoned a secret bottle of wine his purportedly sober wife had stashed in the bedpost. Monk’s “Here’s what happened” might as well be “checkmate.”

45. Season 3, Episode 15: “Mr. Monk and the Election”

We’ve only known Natalie Teeger for five episodes before we get the first attempt on her life. She’s running for school board, when someone shoots up her campaign office and leaves a note demanding that she drop out of the race. But Monk notices that the shooter’s letter refers to her as Natalie Teege, matching a sign in the window of the campaign office that had lost its “r,” and figures out that it’s not actually about her. The scanner Natalie bought at police auction had a dangerous arms dealer’s client list stuck in it, and the shooter was trying to get her to drop out so they wouldn’t discover the evidence. The experience helps Natalie and Monk understand each other a little better, as Natalie admits to her boss that she’s refusing to drop out of the race because she learned that her husband may have deserted his unit when he was killed in action: She doesn’t know what to believe, but she wants to be brave in case he wasn’t.

44. Season 7, Episode 10: “Mr. Monk’s Other Brother”

Monk’s brother Ambrose (John Turturro) is one of the show’s most beloved side characters, so it was a big risk to introduce another brother so late in the series run. Luckily Steve Zahn is up to the task. He shows up to Monk’s house covered in sewage and introduces himself as Jack Jr., a half-brother Monk’s father told him about in “Mr. Monk Meets His Dad.” He’s a con man who needs Monk’s help proving that he didn’t murder a social worker when he escaped from prison. Monk reluctantly agrees, and there’s a really fun tension as Monk tries to figure out how much Jack is lying to him. It’s just a shame we couldn’t get Ambrose to join this family reunion.

43. Season 5, Episode 8: “Mr. Monk Goes to a Rock Concert”

Mr. Monk has plenty of candidates for least-favorite place on earth, but a music festival is a strong contender. He has to suck it up when Stottlemeyer’s son, Jared (Jon Kyle Hansen), runs away to a “rock show,” and Monk’s excited to attend because he thinks they’re talking about a geology exhibit. He begrudgingly sticks around when a roadie named Stork (Terry Fradet) dies of an apparent overdose, but a friend insists he was clean and sober. The episode is mostly about Leland and Jared’s relationship, though. Jared is angry and hurt by his parents’ divorce, and the captain gets a wake-up call that he needs to be more present with his kid.

42. Season 5, Episode 4: “Mr. Monk Can’t See a Thing”

Another episode in which Mr. Monk is pushed way outside of his comfort zone, this one opens at a fire station with Monk losing his eyesight when an intruder throws a corrosive acid in his eyes after murdering one of the firefighters. References to Mr. Magoo abound, including Natalie rebranding the classic cartoon character as a famous blind inventor to make Monk feel better about his handicap. Though he falls into a depression that is somehow also funny, thanks to both the well-calibrated writing and Shalhoub’s fine-tuned performance, Monk still figures out who blinded him and solves another murder in the process. In a rare moment of humility, Monk admits he’s no Magoo.

41. Season 7, Episode 7: “Mr. Monk’s 100th Case”

One hundred episodes is the traditional threshold for television syndication, and Monk celebrated this milestone in a delightfully meta way by setting the episode at a watch party for a TV show about Mr. Monk solving his 100th case. While watching the show, in between Natalie bickering with Leland over flipping channels to watch basketball and Randy flirting with the actress in the reenactments, Monk notices that something was off with one of the murders. He figures out that the show’s host (Eric McCormack) planted evidence while following the investigation, so that he could murder his mistress and blame it on the serial killer Monk is tracking. That means Monk technically solved 101 cases, which drives his OCD crazy and means he’ll have to solve 99 more to retire at an even 200. Thus the syndication celebration doubles as a called shot. (So we’ll need 59 more Monk movies to catch up. Get working on it, Andy!)

40. Season 4, Episode 3: “Mr. Monk Stays In Bed”

It’s a common joke that men are babies when they get sick. That’s doubly (maybe quadruply) true for Mr. Monk, who treats coming down with the flu like he has the bubonic plague, becoming more demanding and paranoid than usual. Monk holes up in bed surrounded by humidifiers, tissues, and his preferred brand of water bottles, even when the entire force is called up to investigate a judge’s disappearance. Monk’s invalid status gives the writers an opportunity for some fun role reversal: Natalie does Monk’s job of investigating when her pizza-delivery driver turns up murdered, and Stottlemeyer does Natalie’s job of taking care of Monk, which he absolutely cannot handle.

39. Season 4, Episode 13: “Mr. Monk and the Big Reward”

Monk’s assistants are (rightfully) frustrated that he refuses to use his talents for monetary gain, so when Natalie needles him into tracking down a stolen diamond to collect the reward, Monk drags his heels — until it becomes a competitive race as other detectives seek to get in on the action. It’s fun to see Monk compared to other classic detective tropes: a Sherlock Holmesian British inspector, a burly bounty hunter, and a geeky tech whiz who relies on gadgets. In the end none of them get the reward. Instead, the police station’s cleaner, Gladys (Davenia McFadden), finds the diamond, which was stuck with gum to the bottom of an interrogation room table by the museum security guard who stole it. It’s a moment of karmic justice for Monk, as he had been harassing Gladys to clean under tables. A clever solution and a reminder to always be nice to your cleaning lady!

38. Season 2, Episode 7: “Mr. Monk and the Sleeping Suspect”

The mystery of this episode — in which the lead suspect in a series of mail bombs has been in a coma for four months — is so compelling, I can forgive the fact that it doesn’t make much sense. The suspect, Brian Babbage (Matt Winston), wanted to kill his siblings so he’d inherit their parents’ entire estate. He figured out how long a parcel would stick to the top of a city mailbox by gluing ketchup bottles to his ceiling and waiting to see how long they’d take to fall. If you think about it for longer than a few seconds, there are so many variables that would affect how fast glue would give out, but whatever. Brian then planned to be in prison when the packages were eventually mailed. We see him at the beginning of the episode flipping off Randy and Leland, leading them in a car chase. He didn’t plan to get hit by a truck while driving away and falling into a coma, but that alibi worked just as well. Or it would have, if Monk didn’t figure it out.

This episode is also the first hint we get that Sharona might not stick around forever when her ex-husband shows up in San Francisco to try and convince her to move back to New Jersey with him, and it establishes her flirtation with Randy. It takes a while for the latter to pay off, but it’s very sweet when it does! (See: “Mr. Monk and Sharona.”)

37. Season 4, Episode 4: “Mr. Monk Goes to the Office”

One of the comedy writers Breckman hired on Monk is fellow Late Night alum Nell Scovell, creator of Sabrina the Teenage Witch and author of a fantastic memoir about the not-so-funny parts of working in a writers’ room. “Mr. Monk Goes to the Office” is the best of the three episodes she penned (“Mr. Monk On Wheels” and “Mr. Monk and the Election” are the other two). It features both a brain-tickling mystery — we see the bad guy force someone to crush their hand in a car door but don’t find out why until Monk’s summation — and a funny workplace comedy pastiche. Mr. Monk goes undercover at a generic office job to find out who crushed the boss’s hand (and killed the parking garage attendant) and it’s like he’s been dropped in the middle of an episode of The Office, complete with a too-intense kiss-ass who’s a stickler for the rules. Somehow, it’s not Mr. Monk.

36. Season 3, Episode 5: “Mr. Monk Meets the Godfather”

Monk has a few run-ins with the mafia over the course of the show’s run (see: “Mr. Monk is Someone Else”) but this encounter stands out thanks to a home-run performance by Philip Baker Hall. The legendary actor plays a Don Corleone-type figure who needs Monk’s help figuring out who shot up his barber shop (that he was using as a front for money laundering, naturally). In addition to featuring perhaps the show’s best single-episode guest star, we also see Monk’s first standoff with a slimy FBI agent and get a sweet Randy and Sharona moment in which he lets her know that the mobster she’s dating was caught on tape admitting to lying to her. The gangster stuff gets a little muddled when the mafia guys suspect a Chinese gang was responsible for the hit, but this episode’s biggest sin is that there’s not enough Philip Baker Hall.

35. Season 8, Episode 14: “Mr. Monk and the Badge”

It’s a testament to the writing that this penultimate episode, in which Monk is finally reinstated to the SFPD only to realize he doesn’t actually want the job, feels both surprising and inevitable. We feel his relief and excitement when he gets the badge back, his frustration at being put on desk duty instead of working a high-profile case, and his loneliness when he’s kept at a distance from Randy and the captain, who aren’t allowed to “babysit” him anymore. He learns what we probably should have known from the beginning — he’s chasing something that doesn’t fit him anymore. It’s a fitting way to wrap up that story line, which leaves the finale free to focus entirely on solving Trudy’s murder.

34. Season 7, Episode 8: “Mr. Monk Gets Hypnotized”

While “Mr. Monk Takes His Medicine” has too much baggage to be fully enjoyable, “Mr. Monk Gets Hypnotized” is just a blast. Monk is reverted to his childhood personality when a hypnotist encourages him to take his mind back to before his pain started. Natalie is shocked when her boss starts jumping in puddles and picking up frogs and overall acting very un-Monk-like. He’s acting so erratic, that when he figures out immediately that a woman is lying when she says her ex-husband kidnapped her and she killed him in self-defense, Stottlemeyer doesn’t believe him and banishes him from the police station. The signature Monk blend of sad and silly is especially strong here, when the little-kid Monk starts to shoulder adult Monk’s loneliness as he wanders the city.

33. Season 2, Episode 10: “Mr. Monk and the Paperboy”

In our first introduction to Kevin Dorfman, Jarrad Paul comes out swinging with his performance as the endearingly annoying quirky neighbor. He’s an excellent foil to Monk’s own eccentricities. We’re mostly just watching Monk read the newspaper in this episode — when his paperboy is murdered, he deduces that someone doesn’t want him to see a certain news story — which doesn’t sound very interesting … on paper. But it’s made dynamic by Kevin’s constant chatter about how he’s fallen in love, distracting the analytical Monk. He solves several cases, including a murder in France, before figuring out that it was actually Kevin whom the murderer wanted to keep the paper away from. He had won the lottery, and Kevin’s new girlfriend was just trying to keep him distracted long enough to kill him before he saw the winning numbers. It’s always lovely when Monk has to acknowledge how much he cares about people in his life — even the people who drive him crazy — which he does in dramatic fashion here, diverting a train from hitting Kevin’s car.

32. Season 3, Episode 14: “Mr. Monk Goes to Vegas”

Randy and Stottlemeyer are in Sin City for a fellow cop’s bachelor party, when a Hangover-style adventure follows (four years before The Hangover was released). The captain drunkenly calls Monk, telling him to meet them in Vegas because he solved a murder, only to have no recollection of the night before once Monk arrives. They have to piece the narrative together while Leland and Randy nurse their hangovers and while dancing around the awkwardness that Monk wasn’t invited to the party to begin with. The episode is essentially a 42-minute ad for the Las Vegas tourism bureau, but it’s a supremely entertaining one.

31. Season 4, Episode 7: “Mr. Monk Goes to a Wedding”

We learn that Natalie’s family is wealthy when she’s left without a date to her brother Jonathan’s (Rob Benedict) wedding and she takes Randy as backup. (“Davenport, like the toothpaste,” the captain remarks upon hearing Natalie’s maiden name. “Not like the toothpaste, we are the toothpaste,” she replies.) Natalie insists that she’s never taken a dime from her parents, but the privileged upbringing adds a new layer to her character, who we’re still getting to know as someone who’s not just a knockoff Sharona. Holland Taylor is perfectly cast as Natalie’s cold, critical mother, helping us understand why Natalie doesn’t have much contact with her family even as we can’t help but be charmed by Taylor’s perfectly calibrated bitchiness. (It’s giving Emily Gilmore.) Unfortunately the black-widow story line falls a little flat, as we never quite believe Jonathan will be murdered by his sinister bride-to-be.

30. Season 2, Episode 6: “Mr. Monk Goes to the Theater”

Sharona’s sister Gail returns in season two, when she’s accused of murdering her co-star in a play. She was supposed to stab him with a stage knife — which she swears she did — but he collapses onstage with a real knife in his chest. The personal connection makes the mystery more engaging, especially since we know how fraught Sharona’s relationship with Gail is. Tony Shalhoub also gets a very funny scene here, when Monk is asked to take the murdered actor’s place. It’s delightful to watch a talented performer acting like a bad actor, and the stakes are raised when Monk figures out that Gail’s understudy is behind the murder while onstage with her. She had rubbed peanut oil — which the actor was allergic to — on an apple he ate in the play; her father, pretending to be a doctor, rushed onstage and put a real knife in his chest. We’ll let it slide that anaphylactic shock looks nothing like being stabbed to death.

29. Season 4, Episode 10: “Mr. Monk Goes to a Fashion Show”

One of Monk’s most overtly satirical episodes is this season-four standout featuring Malcolm McDowell as a tyrannical fashion designer named Julian Hodge who murdered a model and pinned it on a delivery boy named Pablo Ortiz (Alejandro Chaban). Monk gets involved in the case when Pablo’s mother, his favorite shirt inspector, is so distracted that she starts to miss flaws in the garments. The case seems like a slam dunk since Pablo’s DNA was found at the scene and the model’s roommate said he was stalking her, but Monk eventually figures out that Hodge paid off the roommate and the SFPD’s forensic specialist (Scott Adsit) to help frame Pablo. While investigating the case, Monk is baffled when his friends try to impress the exacting and cruel Hodge, leading to a funny scene where Natalie and Randy compete to see who can look the most chic while visiting a fashion shoot. But it’s Julie who catches the designer’s eye, and he hires her to walk in an upcoming show. There are so many specific jokes about fashion that I have to assume the episode’s writer, Jonathan Collier, worked in the industry at some point. Either that or he just watched a lot of America’s Next Top Model.

28. Season 3, Episode 3: “Mr. Monk and the Blackout”

Monk is in the dark, literally, in this episode about a blackout that hits San Francisco. When the outage is found to be intentional — and seemingly an inside job — the power company’s PR rep, Michelle Rivas (Alicia Coppola), hires Monk to investigate. But she has an ulterior motive: She’s into Monk. This is the first time we see a woman actively show an interest in dating Monk, but she pretty quickly becomes disillusioned with the prospect when he refuses to take the elevator to a restaurant on the 52nd floor. The blackout is a clever way to throw Monk off balance, a tactic that the writers would use to more dramatic effect in “Mr. Monk Can’t See a Thing,” and there’s a fun callback to Monk’s Willie Nelson connection (see: “Mr. Monk and the Red-Headed Stranger”).

27. Season 5, Episode 6: “Mr. Monk and the Class Reunion”

We can forgive the fact that this story line, about Monk attending his college reunion, is sort of a reskin of “Mr. Monk Goes Back to School” for two reasons. One is that we see the beginnings of Monk and Trudy’s courtship, an essential piece in how Monk became Monk. The other reason is that the mystery is really good. Monk is confused when Trudy’s friend Dianne (Cynthia Stevenson) tells him that her husband, Kyle (Brian McNamara), is excited to meet him, but when Kyle arrives he doesn’t know that Monk is a detective. Other weird stuff keeps happening around Kyle, seemingly a series of coincidences that mirror Dianne’s experiences at college. Eventually Monk figures out that Kyle had found a suicide note Dianne wrote when she was depressed in school and came up with a plan to kill her at the reunion. He needed to re-create the events she wrote about in her note — including eating at a diner with Adrian and Trudy. (Kyle found a random woman named Trudy to join them.) The most satisfying Monk summations feel like puzzle pieces fitting into place, finally revealing the whole picture.

26. Season 5, Episode 9: “Mr. Monk Meets His Dad”

Monk’s season-five Christmas episode fully captured the spirit of the season: It’s about family, with all the magic and the baggage that entails all swirling together like a mulled wine. We finally meet Monk’s dad, Jack (Dan Hedaya), who left the family when Adrian was five, when he’s arrested on speeding charges on his way through San Francisco as a long-haul trucker. Jack asks for his son’s forgiveness — and help fixing the ticket — when Stottlemeyer convinces Adrian to join his dad on his route for some long-overdue father-son bonding. We see Jack’s boss at the trucking company murder his partner in the opening scenes of the episode, but crime solving takes a backseat to emotional storytelling, which means this episode spins its wheels for a while before Monk finally figures out what happened. (That was two truck puns. Merry Christmas.)

25. Season 3, Episode 13: “Mr. Monk Gets Stuck in Traffic

A handful of musicians have appeared on Monk, either as themselves (see: “Mr. Monk and the Red-Headed Stranger”) or as heightened, parodied versions of themselves (see: “Mr. Monk and the Rapper”). But the most delightfully incongruous musical guests on Monk are nü metal icons Korn, who open their tour bus bathroom to Julie when she has to pee while they’re stuck in traffic behind the scene of a car crash. Also delightful: Larry Miller, who plays a fellow traveler who follows Monk around as he tries to figure out what caused the crash, after observing that it couldn’t be an accident. A highway traffic jam is a clever take on a locked-door mystery, plus there are some compelling emotional stakes as a still-new Natalie nearly quits due to Mr. Monk’s lack of empathy when she sprains her wrist. He makes it up to her later by unbuckling his seat belt and leaning out the window while speeding down the highway in order to rescue her from a dump truck driven by the killer who staged the accident. They both agree that their relationship is a two-way street. (That pun is in the episode, I can’t take credit for it.)

24. Season 4, Episode 15: “Mr Monk Goes to the Dentist”

It’s always fun when Randy, who frequently throws out crazy theories that aren’t even worth a response from the captain, gets one right. Of course no one believes Randy when he insists that his dentist (Jon Favreau) and his assistant (Brooke Langton) killed someone while he was getting a cavity filled, since he was under anesthesia at the time. The dentist laughs off Randy’s accusation, insisting that people say all sorts of things while sedated, but Randy is so frustrated by his colleagues laughing at him that he quits the force in anger. It’s here that we get Randy’s best moment of the series: He revives his high-school band called the Randy Disher Project and writes a desperate song about how he’s “tired of sucking up” and he doesn’t “need your mustache.” It’s charming and cringe at the same time, just like Randy. (His song “I Don’t Need a Badge” is lovingly referenced several times for the rest of the show’s run and even pops back up in Mr. Monk’s Last Case.) Randy gets the last laugh, though, when Monk figures out that the murder really did take place; a patient had admitted to an armored-car robbery while under sedation and returned to confront his dentist after figuring out that he’d taken the stolen bonds. They weren’t lying about people saying crazy things on anesthesia!

23. Season 2, Episode 1: “Mr. Monk Goes Back to School”

Another great villain who thinks he’s smarter than Monk at his own peril, this Columbo-style episode heavily implies that science teacher Derek Philby (Andrew McCarthy) murdered his fellow teacher and mistress, Beth Landow (Erica Yoder), and made it look like she jumped off the school’s clock tower while he was proctoring the SAT, but we don’t know how he did it until Monk’s summation. And the “how” is extremely funny, with a sort of classic detective story logic. Philby had murdered Beth before the test, at 8:15 a.m., and laid her body out on the horizontal clock hand. As the minutes ticked past and the hand rounded the clock, the body slid off and hit Philby’s car, which he’d parked below the tower in order. McCarthy is so good as the arrogant bully who thinks he’s outsmarted Monk, it’s extra satisfying when Monk gets him to incriminate himself.

22. Season 4, Episode 1: “Mr. Monk and the Other Detective”

Monk’s ego faces its greatest test when another private detective seems to be even better at solving crimes than he is. Jason Alexander guest stars as Marty Eels, the other detective who shatters Monk’s already fragile sense of self when he shows up at a murder scene and appears to have all the answers. Not only is Alexander a fabulous choice to play the “professional pain in the ass,” according to Stottlemeyer, but little comments like that are a great example of how Monk writers build out their world. Rather than just some random guy showing up, they all know Marty as a hack, which makes his apparent brilliance even more annoying. As it turns out, Eels is “cheating” — his mom is an airline phone operator and heard the murderers discussing their crime while they were on hold buying tickets.

21. Season 3, Episode 2: “Mr. Monk and the Panic Room”

Some Monk premises you can just tell were green lit because they made the writers room laugh hard enough. “Monkey murderer” is one of those premises. Monk has to prove that a pet chimpanzee named Darwin didn’t kill his owner, music producer Ian Blackburn (Stewart Finlay-McLennan), when they were found locked together in a panic room, Blackburn with a gunshot wound to the back of the head and Darwin holding a gun. There are just so many avenues for comedy with a killer monkey, from Monk’s pristine apartment getting trashed by the wild animal to Stottlemeyer trying to provoke Darwin in order to prove that a chimp can shoot a gun. The side plot about Sharona proving to Benjy that it’s okay to stand up to bullies is a little ham-fisted, but who cares when we’re having this much fun?

20. Season 2, Episode 15: “Mr. Monk Gets Married”

Monk and Sharona’s relationship is the highlight of those early seasons. Though Natalie will become a vital character in her own right, the bond between Monk and the nurse who helped him through his mental breakdown when Trudy died is just too special to replicate. That relationship is put to the test in “Mr. Monk Gets Married,” when Monk and Sharona go undercover at a couple’s retreat to figure out what’s going on with Randy’s mom (Susan Kellermann), who recently got married in a whirlwind romance only for her new, much younger husband, Dalton Padron (Nestor Carbonell), to immediately insist they need couple’s therapy. While there’s never any romantic tension between Monk and Sharona, their blend of annoyance and affection is close enough to a marriage that the couple’s therapist (a perfectly cast Jane Lynch) insists they need special help.

19. Season 2, Episode 8: “Mr. Monk Meets the Playboy”

With apologies to all the other self-perceived geniuses who dismiss Monk as a strange nuisance, one of them stands out because he’s played by Gary Cole. The versatile character actor plays a sleazy computer nerd turned playboy mogul named Dexter Larson. The episode follows a classic Monk format, where we see a death happen that appears accidental. Larson’s publisher tells him that they’re going to cancel his men’s magazine, Sapphire; the next morning he’s strangled by a barbell in his home gym. Larson is obviously responsible, but how? He stood under the floor with a super-powerful magnet, of course. The solution is so dumb it’s brilliant, and Gary Cole sells Larson’s disbelief at being bested by Monk so, so well.

18. Season 7, Episode 1: “Mr. Monk Buys a House”

Real-life tragedy bled into Monk’s fictional sadness when actor Stanley Kamel died of a heart attack between seasons six and seven. Monk’s grief over losing his beloved psychiatrist surely mirrors the grief felt by the show’s cast and crew; Adrian struggles to find a new therapist because no one can fill Dr. Kroger’s shoes. In addition to the lovely tribute to Kamel, though, it’s got a really excellent mystery, with Brad Garrett guest starring as a handyman named “Honest” Jake, who really earns those scare quotes. Monk buys an elderly man’s house to get away from his neighbor’s piano playing, but he soon figures out that the man was murdered by his nurse when he admitted to her that there was money hidden somewhere in the house. She tells her boyfriend, Jake, about it, and he convinces Monk to let him smash up the house’s walls under the guise of finding structural problems he needs to fix. By episode’s end Monk finds a worthy enough replacement for Dr. Kroger — for both him and us — in Hector Elizondo’s Dr. Bell, who helps Monk realize that the piano was bothering him because it was a song that he used to hear in Dr. Kroger’s waiting room. Monk moves back into his apartment (and presumably has a hell of a time selling a smashed-up house).

17. Season 5, Episode 10: “Mr. Monk and the Leper”

USA aired two versions of this episode: one in color and the other in black and white, but the black-and-white rendition is far superior. As an homage to noir movies, the black-and-white take on the episode isn’t just a thematic novelty — it also works practically to help conceal the fact that the titular leper, Derek Bronson (Stephen Bogardus), doesn’t actually have leprosy. (In the color version it’s more obvious that his lesions are makeup, but that could fairly be attributed to TV magic.) He’s counting on Mr. Monk’s germophobia to keep him from looking too closely when he admits that he faked his death eight years ago, and asks Monk to help him destroy some papers that would indicate to his wife, Mandy (Sarah Joy Brown), that he was having an affair, which he says will crush her. It’s all a setup, though, and the man isn’t actually Derek Bronson — it’s Mandy’s boyfriend in makeup and bandages. They need a judge to believe that Bronson is alive and wants to leave his fortune to his wife instead of his nephews, as he wrote in his will. They knew that Monk would be an unimpeachable witness. The double crossings and secret identities play into the noir of it all, as does the over-the-top climax in which Monk dangles off the side of a hot-air balloon to avoid being shot by Mandy.

16. Season 2, Episode 11: “Mr. Monk and the Three Pies”

Ambrose is here! Monk’s very own Mycroft Holmes, Ambrose is just as smart and observant as his brother, but as an agoraphobe who hasn’t left his house in over 30 years, he makes his living writing instruction manuals. The relationship between the two brothers is the focus of the episode, as we learn they’ve been estranged since Trudy died. Adrian resents his brother for not reaching out when he was suffering, but Ambrose kept the distance because he blamed himself for her death since she was running an errand for him when she died. John Turturro and Tony Shalhoub convey those years of tension with a barbed sort of chemistry, and while “Mr. Monk Goes Home Again” develops that chemistry even further, this introduction to Ambrose is nearly as good for how it establishes Monk’s background while giving us a recurring character so beloved it’s easy to forget he only appears in these two episodes (plus a quick cameo in “Mr. Monk’s 100th Case”).

15. Season 4, Episode 5: “Mr. Monk Gets Drunk”

Drunk acting is an art — just ask Catherine O’Hara — and Tony Shalhoub proves to be an artist in this episode that sees Monk visiting the winery where he and Trudy honeymooned. The typically teetotaling Monk gets well and plastered when he drinks a full carafe of what he thinks is nonalcoholic wine in an attempt to loosen up a witness. He’s investigating a fellow guest’s disappearance — a guest whom the rest of the resort’s guests and staff insist never existed. In a classic whodunnit twist, everyone is in on the crime. The missing man (Daniel Roebuck) had stolen money from the mob and was hiding out in wine country when he died of a heart attack in his room. Rather than report his death, the guests who found him decide to split the money and pretend they’d never seen or heard of the man. It’s the most Agatha Christie–ish Monk ever got.

14. Season 6, Episode 1: “Mr. Monk and his Biggest Fan”

Sarah Silverman’s character of obsessed fan Marci Maven was so good in (spoiler alert) Monk’s best episode, she came back for an episode entirely her own. While the episode suffers a tiny bit from the Captain Jack Sparrow problem — moving a comic-relief side character into the spotlight, to diminishing returns — it’s packed with so many great meta jokes that it’s easily overlooked. Marci’s first episode, “Mr. Monk and the TV Star,” is the most self-referential Monk ever gets, but this episode is a close second. With references to previous episodes and Monk fanfiction, Marci’s obsession with Mr. Monk can be read as (loving) ribbing of Monk fans. (More on that later.)

13. Season 4, Episode 11: “Mr. Monk Bumps His Head”

“Mr. Monk Bumps His Head” breaks some rules for what makes a good Monk episode. Monk is on his own, without Natalie, Stottlemeyer, or Randy, for most of the episode, and it does a mean little bait-and-switch at the beginning by making us think Monk has a new lead on the six-fingered man. But it all works, thanks in large part to Laurie Metcalf, who was nominated for an Emmy for her guest performance as an eccentric woman named Cora. Monk is hit over the head and left on a truck bed by a con artist who gives him forged information about the man who killed Trudy. When he’s discovered by the trucker he has no memory of who he is. Unfortunately for Monk, Cora spots him and is more than happy to give him a new identity — as her new husband, Jerry. It’s so fun to watch Monk chafe against this new life while his natural talents for deduction shine through the amnesia, as he solves the disappearance of a local waitress. It’s even more fun to watch Cora scold him for it, insisting that he’s a roofer and definitely doesn’t have a fear of heights. Laurie Metcalf deserved that Emmy!

12. Season 6 Episode 2: “Mr. Monk and the Rapper”

Monk is especially enjoyable if you’re a little stoned, so it was only a matter of time before Snoop Dogg showed up. Snoop doesn’t just guest star as a gangsta rapper, unluckily named Murderuss, who’s accused of killing his rival, Extra Large (Marcello Thedford), with a car bomb. (Even more unluckily, Murderuss has a hit song called “Car Bomb.”) He also contributes a rap version of Randy Newman’s iconic theme song, which legitimately slaps. That’s not the only Snoop track that makes the episode though. Murderuss raps the “Here’s what happened,” explaining that he was set up and the bomb was planted by the head of Extra Large’s record label, who planned to kill his partner but forgot to account for daylight saving time when he set the timer.

11. Season 2, Episode 4: “Mr. Monk Goes to the Circus”

Good Monk episodes have both a compelling mystery and emotional stakes to keep you invested. Great Monk episodes, like this one, weave the two together in a neat little package. Monk has to visit the circus when its ringmaster is murdered by a masked acrobat. The main suspect, his ex-wife, Natasha (Lolita Davidovich), is a trapeze artist, but she has a broken leg from when she fell a few days earlier so couldn’t possibly have somersaulted away from the scene of the crime. While investigating, Sharona reveals that she has a deadly fear of elephants, which Monk dismisses as silly and tells her to “suck it up.” Obviously that’s extremely rich coming from a man with, by his own count, 312 phobias. The tension is ratcheted up even further when, while the elephant Dede’s trainer tries to prove to Sharona that elephants are harmless, Natasha commands Dede to step on his head with a walkie-talkie taped inside her ear. It turns out she didn’t injure her leg in the fall after all; she pretended to fall and then had the elephant step on her leg after she murdered her ex. The trainer saw her do it, so she killed him too. The trauma of witnessing something so brutal is enough for Monk to see that he needs to be more compassionate toward Sharona, and after they catch Natasha by finding her fingerprints on the walkie’s batteries, she even consents to feed Dede.

10. Season 4, Episode 15: “Mr. Monk Gets Jury Duty”

This 12 Angry Men homage was a slam dunk for Monk, with Tony Shalhoub playing an offbeat version of the Henry Fonda classic. Monk, like Fonda’s Juror 8, is the lone “not guilty” vote on a jury in what appears to be an open-and-shut case. As he tries to convince his fellow jurors of the young defendant’s innocence, he chafes at the experience of working as a team. Monk’s eccentricities are merely annoying when he’s brought in as an expert; to the jury of his peers, they’re a frustrating hindrance. Like the film it’s inspired by, “Mr. Monk Gets Jury Duty” is electric when it’s ratcheting up the tension between jurors, so we can ignore the fact that, as an active contractor for the SFPD, he probably would be dismissed from a jury pretty quickly.

9. Season 1, Episode 13: “Mr. Monk and the Airplane”

An enclosed space and a ticking clock give this episode a jittery momentum, as, while on a flight to New Jersey with Sharona, Monk becomes convinced that a fellow passenger killed his wife and replaced her with a doppelgänger. It’s not the most clever mystery — the doppelgänger is terrible at pretending to be the dead wife — but there are so many fun, meta jokes that the crime is almost an afterthought. Tony Shalhoub’s Wings costar Tim Daly is here playing himself, and Sharona is starstruck. When Monk asks her if the show was good, she replies, deadpan, “He was.” It’s also the first time we see Brooke Adams, as a flight attendant who absolutely cannot stand Mr. Monk. Add Garry Marshall and an annoying little girl (Haylee Wanstall) to drive Monk crazy, and you’ve got one of the most fun Monk episodes ever aired.

8. Season 1, Episode 10: “Mr. Monk Takes a Vacation”

It’s a beach episode! Sharona takes Monk on vacation with her and Benjy, forgetting the fact that murder follows him everywhere. Monk has some nice bonding with Benjy when the kid witnesses a murder through some beach binoculars, but no one believes him because the room where he saw a woman die is squeaky clean. The lack of Randy and the captain is made up for by Polly Draper as the hotel’s security chief, Rita Bronwyn, who is only too excited to solve a real crime. This is the platonic ideal of a Monk destination episode: We get lots of jokes about Monk made uncomfortable by new surroundings (a resort comedian roasts him for hitting the beach in a full suit), friction with a new authority figure who doesn’t appreciate Monk’s gifts (the resort’s manager, who just wants to avoid a scene), and a last-minute solve that ties everything together (Benjy saw the hotel’s maids murdering one of their own, who were able to clean up the scene so quickly, then hid the body in a suitcase in the lobby).

7. Season 3, Episode 6: “Mr. Monk and the Girl Who Cried Wolf”

The scariest episode of Monk is also one of its sweetest, as Sharona thinks she’s going insane when she starts to see a dead man following her around. There are some nasty jump scares (or as nasty as a blue-sky show will get) of the man with a screwdriver in his neck and other gory effects. Sharona, it turns out, is being gaslit by her creative writing teacher, who planned to use details from one of Sharona’s stories to murder her husband but needed to first discredit Sharona so she couldn’t tell the police about it. But before Monk figures that out, he’s at a loss for how to help his assistant — and friend — and it’s heartbreaking to watch them both feel so helpless. But this is Monk, so there are plenty of funny moments, too, especially when Sharona asks her friend Varla (Niecy Nash!) to fill in for her as Monk’s assistant. This is also the first time we, and Monk, meet Harold Krenshaw, when they run into each other in Dr. Kroger’s waiting room after a scheduling mix-up.

6. Season 5, Episode 1: “Mr. Monk and the Actor”

Tony Shalhoub is reunited with his Big Night costar Stanley Tucci in this episode about an actor who’s set to play Monk in a TV movie. It’s the most meta the show ever got, with lots of little in-jokes, most likely including some that went over our heads but were references just for the show’s staff. For example, allusions are made to an unseen producer named Hoberman, which is, of course, also the name of Monk’s producer. The TV movie in question is a reenactment of the “killer astronaut” case (see “Mr. Monk and the Astronaut”) and Tucci’s actor character, David Ruskin, wants to spend some time shadowing Monk to learn his ways. The method actor can’t handle Monk’s darkness, and the button on this episode-long joke is that Ruskin is in England playing a less depressing character — Hamlet.

5. Season 4, Episode 2: “Mr. Monk Goes Home Again”

The Ambrose-Adrian relationship gets its full due in this Halloween episode. With their awkward reunion out of the way, the writers have ample runway to explore these brothers’ relationship when Monk returns to his childhood home. Ambrose told him their dad called and wanted to see them. They act much more like brothers here — or at least like Monk brothers — pedantically one-upping each other (Ambrose keeps correcting everyone that the guy dressed as Frankenstein who tried to steal his candy should be referred to as “Frankenstein’s monster”) and bickering over whether they can clean out their dad’s office. When it becomes clear that the Frankenstein(’s monster) was trying to steal the candy because he poisoned one of the bars, it seems like Ambrose might be in actual peril, since he ate one of the candies. Monk and his assistants are often put into danger, but we can assume that they’ll be fine; the likelihood of a series regular getting killed off is pretty slim. There was an actual possibility that the Monk writers could kill Ambrose after wrapping his story line. Instead, he pulls through, and comes back home to a note on the door from Jack, saying that he didn’t blame them for not wanting to see him, and that he was proud of Ambrose for leaving the house. Someone hand me a tissue.

4. Season 1, Episode 12: “Mr. Monk and the Red-Headed Stranger”

I mean … it’s Willie Nelson. Next entry.

Just kidding, but the arrival of the “Red-Headed Stranger” does feel like a thrown-down gauntlet in this early Monk episode. The show is calling its shot for the quality of guest stars that it would feature across its run. As this list indicates, there are plenty of iconic performers that made their way to Monk, but this first one is the most special. It’s also just a really tight episode of television. Willie Nelson is accused of murdering his tour manager, Sonny (David Anderson), whom he caught stealing money, because a blind woman named Wendy (Jackie Richardson) identified his voice at the scene of the crime. But Monk figures out that she’s not really blind — she lost her vision in a childhood accident, and slowly regained it as an adult — when she laughs at a streaker who has been pissing off the captain for most of the episode. What could have been just a funny little bit is part of the whole puzzle, a great little trick that Monk frequently attempts, to mixed results. But the writers pull off a further trick with one of the rare instances where a murder feels somewhat justified; Sonny caused the crash that blinded Wendy and killed her parents, and she killed him in revenge. It’s a rare moment of moral ambiguity for the typically black-and-white procedural format, with the perfect bittersweet soundtrack to match.

3. Season 3, Episode 16: “Mr. Monk and the Kid”

We don’t hear much about Trudy and Adrian’s plans for children, but this, Monk’s saddest episode, explores Monk’s fears and hopes for parenthood when he reluctantly takes in a foster kid named Tommy (Preston Shores) who found a severed finger in the park. We watch Monk open his heart to this little boy and then watch it break when he realizes he can’t care for him the way he needs to be cared for, since he can barely care for himself. Monk verbalizes this all in a story he tells Tommy, which also doubles as the “Here’s what happened,” when he figures out that Tommy’s foster mother (Nicole Sullivan) had kidnapped a man and planned to present his severed finger as extortion. There are, of course, some very funny moments as Monk figures out how messy and stressful a toddler is, but rather than simply providing comic relief, they are later framed as evidence for Monk’s unsuitability as a father. It’s devastating, especially since it’s Monk himself coming to that conclusion, as we recognize the full extent of what Trudy’s loss took from him.

2. Season 4, Episode 14: “Mr. Monk and the Astronaut”

This is the platonic ideal of Monk’s Columbo-style episodes. It has it all! We know who the murderer is right away but not how he did it, providing us with a fun puzzle to solve while giving Monk a nemesis to square up against. And this nemesis, astronaut Steve Wagner (Jeffrey Donovan) is one of the worst/best we’ve ever seen. He outright bullies Monk in front of Julie’s class, calling him weak and encouraging the kids to aim their laser pointers at Monk, which would honestly annoy anyone. It is supremely satisfying, then, when Monk stops Wagner from destroying evidence by literally standing in front of his airplane. Not so weak, buddy! I can’t prove that this episode was so good it got Jeffrey Donovan his own show, but it aired in 2006 and Burn Notice premiered in 2007, so you do the math.

1. Season 2, Episode 12: “Mr. Monk and the TV Star”

Not to be confused with “Mr. Monk and the Actor,” “Mr. Monk and the TV Star” is the best episode of Monk for how it pulls together every element that makes the show great. There’s a winking but still goofy humor, quirky side characters, and enough personal stakes for Monk to give the mystery an emotional weight. Billy Burke guest stars as an actor named Brad Terry who plays the lead on a cop show called Crime Lab S.F. The Monk writers here do a lot of riffing on cop shows that allow us to feel like we’re in on the joke, especially with Crime Lab S.F. as an obvious stand-in for CSI, down to its made-up tech (Stottlemeyer scoffs at the show’s “spectroscope”). “We know this is just a show, it’s not really how cops act. That’s fine! It’s just TV,” the writers seem to be implying. Monk, more than any other procedural, acknowledges that tension, and takes it a step further by having fun with it.

This is also where we meet Sarah Silverman’s Marci Maven, who’s introduced as an obsessed fan of Terry’s. Cast before Silverman’s career took off, the character is openly mocking Monk viewers when she complains about Crime Lab S.F. changing their theme song; in real life, Randy Newman’s iconic “It’s a Jungle Out There” replaced a jaunty instrumental theme during Monk’s second season, which a vocal contingent of the fanbase was not happy with. (To be fair,  much of the fanbase is made up of boomers who fear all change.) But it’s a gentle mocking, which is exactly what makes Monk so fun. Please, roast me, Andy! Monk shows us that we can tease each other about our obsessions — and sometimes even annoy the crap out of each other with them — but they make us who we are. Loving our friends not in spite of their eccentricities, but as essential to what we love about them, should be Monk’s lasting legacy. That, and the fact that milk is actually really scary.

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