This week, we’re highlighting 24 talented writers and performers for Vulture’s annual list “The Comedians You Should and Will Know.” Our goal is to introduce a wider audience to the talent that has the comedy community and industry buzzing. (You can read more about our methodology at the link above.) We asked the comedians on the list to answer a series of questions about their work, performing, goals for the future, and more. Next up is Chloé Hilliard.
Tell us a story from your childhood that you think might explain why you ended up becoming a comedian.
I was in eighth-grade math class. My teacher, Mr. Cracco, was making an analogy using Michael Jordan. This was 1993 — we’re talking the prime Chicago Bulls, back-to-back championships, Jordan era. Mr. Cracco asks, “What is Michael Jordan known for?” I yell out, “Gambling!” Mr. Cracco loses it. He’s laughing, but he has to compose himself and chastise me for being disruptive. I wasn’t trying to be funny. At that time, Michael Jordan was in the press for admitting to a $57,000 golf-gambling debt. I was stating the truth; I was answering the question. I was sent into the hallway on a “time out.” That’s when I learned that the truth is always the best punch line. “It’s funny because it’s true” is my favorite compliment to receive as a comedian.
If you were immortalized as a cartoon character, what would your outfit be?
A cropped vintage graphic T-shirt, jeans, white Chuck Taylors, cool shades.
What’s your proudest moment/achievement of your comedy career so far?
Independently producing my debut comedy album, Big Dick Energy, with my late friend and collaborator Tim Moore.
Which comedian’s career trajectory would you most like to follow?
Jordan Peele.
Tell us everything about your worst show ever. (This can involve venue, audience, other acts on the lineup, anything!)
Between 2013 and 2020, I spent most of my time on the road performing at colleges across the country. I was booked to headline a college in Florida. My opening act was a heavyset dude whose closing bit involved him stripping down to a hot-pink thong. I swore a facility member was going to flag it, because this is a grown-ass man stripping down to a thong in front of college kids, mainly freshmen. The students loved it — standing ovation. I go up with my jokes and walked two-thirds of the crowd within minutes. A grown man in a thong humbled me.
What have you learned about your own joke-writing process that you didn’t know when you started?
I can’t sit down and write a joke. When I first started, I’d dedicate time to write and come up with the hackiest shit — imagined premises, weird scenarios that never happened but for the purpose of the joke. It was so disingenuous and read as contrived onstage. As I grew comfortable in myself, I learned that my best material comes from life, encounters, observations, conversations, and research. I was a journalist for over a decade before I got onstage. My approach to comedy is Y’all see this!? I’m not crazy, right?
What’s the biggest financial hurdle you’ve encountered since becoming a comedian?
I was very fortunate that I started doing colleges early in my comedy career. I started out being paid $1,200 to do an hour. I didn’t have the hour, but I made it work, and over time I got better and could command more money. I made more money performing at colleges than I ever did as a journalist. That allowed me a financial and creative freedom to do what I wanted to in comedy. I could take risks, say “no,” and bet on myself.
At the end of the movie 8 Mile, Eminem’s character, B-Rabbit, starts his final battle rap by dissing himself so the person he’s battling has nothing left to attack. How would you roast yourself so the other person would have nothing to say?
I’m six-foot-one and been this height since I was 12. I can’t snap my fingers. I’m not having kids.
When it comes to your comedy opinions — about material, performing, audience, trends you want to kill/revive, the industry, etc. — what hill will you die on?
Stop with the “viral” crowdwork moments. It’s giving harassment. Setting up cameras and pointing at the audience sets off a domino effect of bad behaviors in the comedy club. The comedian isn’t bringing their A-game and is relying on the audience to do the heavy lifting. The audience gets entitled and expects to be the center of attention. At the end of the experience, there isn’t one joke or moment that you walk away with the feeling of Wow! That was an amazing experience. No one is retelling your crowdwork riff to their friends. Stop being lazy.
What is the best comedy advice, and then the worst comedy advice, you’ve ever received?
Best: When you’re onstage, you are in control.
Worst: I need to spend thousands of dollars a month on targeted social-media ads in order to grow my fan base.
