For the first road trip of his "Late Show" in all its glory, Stephen Colbert chose the place where he cut his comic teeth and the time when it would be commanding the world's attention.
The former Second City performer presided over four live episodes at the Auditorium Theatre, finding fun not just in the Democratic National Convention but also in the quirks of its host city. Here are five highlights from the week:
The host brought back an old character named Donny Franks — a living, breathing, nasal-talking Chicago stereotype created during a visit to Wrigley Field in 2016.
In aviator sunglasses, a shaggy wig and a goatee, Donny stopped by the DNC to hawk not just Vienna Beef but also ill-conceived political merch like a T-shirt reading "Ballz to the Walz."
He got a primary primer from Rep. Alexandria Ocasio-Cortez, drank Old Style with James Carville and quizzed Gov. JB Pritzker about his encased meat habits.
"Terrorists are gonna blow up the bean unless you have ketchup on a hot dog," he quizzed in a thick Chicago accent. "Do you eat ketchup on a hot dog?"
"Mustard only," the governor replied.
Said Donny, "That’s the right answer."
Wednesday's musical guest, Chance the Rapper, performed as Chicago artist Tyrue “Slang” Jones drew murals behind him.
Chance's song, “Together,” is a call for community and family connection that references Harold's Chicken Shack and the Bud Billiken Parade in reminiscing about the musician's Chicago youth.
The crowd cheered Chance's lyric calling out Barack Obama in support of community benefit agreements that ensure neighborhood benefits from developers: "We need CBA, CBA, CBA, Barry / Before they build another presidential library."
The week's heated demonstrations over the war in Gaza spilled into the Auditorium on Tuesday as protesters attempted to interrupt Colbert's interview with former Speaker of the House Nancy Pelosi.
Instead of ignoring the activists or snapping at them, Colbert calmly acknowledged them and even confronted Pelosi about their concerns, saying her diplomatic commentary about the war was clearly "unsatisfying" to the vocal folks in the crowd.
"They've said the United States should not have any role in supplying Israel with arms to kill the people of Gaza," he said, relaying what he was hearing.
"Israel has a right to defend itself," Pelosi responded, "and the hostages should be returned. But the part of it that's been so major for all of us for so many years is that there must be a two-state solution. We cannot have peace unless there's a two-state solution."
The outbursts resumed while she spoke, prompting Colbert to turn to the audience and order, "Please don't interrupt my guest."
To supplement the "Star Spangled Banner" renditions heard nightly at the DNC, Colbert and his team wrote alternate lyrics paying tribute to Chicago's greatest traditions (or, some might say, hoariest cliches), from Italian beef and deep-dish pizza to the dyeing of the Chicago River.
The host handled lead vocals in a music video, with help from Sean Hayes, Jason Sudeikis and Jennifer Hudson, who added a flourish to the Cubs-centric line "The Yankees can go to hell for taking Rizzo."
To wrap it up, Colbert bounced from Clark Street to Millennium Park to sing:
At The Wiener's Circle they surely lo-o-o-ove to swear
O'er the land of The Bean
And the home of Da Bears!
Of course, for those last two words, George Wendt and Robert Smigel chimed in, wearing full Superfans finery.
Just hours after she spoke to the Democratic National Convention, former Secretary of State Hillary Clinton scooted over to the Auditorium to tell Colbert the atmosphere at the United Center "was incredible. It was electrifying."
Replied Colbert, "I would say it's the second best audience in Chicago tonight."
The Maine South High School grad bragged that she has "a huge number of friends who still would never put ketchup on a hot dog."
Clinton urged her interviewer to return to town at least once a month.
"Every time I'm in Chicago I think, 'Why did I ever leave?' " Colbert said. "This is the greatest city in the world."
