Comedian Lil Rel Howery has come a long way from Chicago’s West Side and from his early days as a standup comic here. But lately, he’s spent a lot of time on screen, with credits that include a role in Jordan Peele’s Academy Award-winning film “Get Out,” NBC’s “The Carmichael Show” and even his own sitcom, “Rel,” on FOX.
Now, he’s coming home. Last weekend, Howery filmed his latest standup special at Black Ensemble Theatre. The homecoming show is part of the What’s Funny Comedy Festival, running through Sept. 26, which Howery cofounded with his former manager Knowledge Beckom.
“Some of the best musicals I’ve ever seen have been at Black Ensemble,” said Howery. “I’ve been on Broadway. I’ve seen a lot of stuff. Nothing is better than a Jackie Taylor show. I’m really hoping to build a relationship with them beyond just this special.”
Beckom said the festival came about organically. In 2024, he casually mentioned the idea of a comedy festival to Howery, who just so happened to be looking for a way to give back to Chicago. “Once I understood where he was at, and where I wanted to go, it just made sense,” said Beckom. “We’ve been at it ever since.”
This year’s festival — hosted through Saturday at venues across Chicago — brings together experienced comedians and up-and-comers, such as Baltimore’s Cheja “Che Che” Tucker. The fest will honor legend Bill Bellamy with the 2026 Icon Award.
“We want a blended festival,” said Beckom. “I don’t want 90% men. I want women comics. About 40% of people performing this year are from out of town. We’re looking at them beyond just being funny on stage, but who looks like they have a story to tell? Chicago’s always been the market to show people who’s up next.”
Even with the heavy crop of talent traveling for the festival, the headline event will be the taping of Howery’s new special. And the content of his performance will hit close to home.
“My dad passed in January, and while I was planning the funeral, comedy kept showing up,” he said. “I told my brother after the funeral, ‘I want to do a special dedicated to dad.’ Everything I’m doing the next few weeks in Chicago — the comedy festival, and I’m shooting a limited series that I wrote and created — it’s a love letter to my family. It’s my love letter to Chicago and to the way I grew up.”
Chicago has established itself as a premier destination for comedy and for standups, specifically Black standups. The city’s clubs provide a fertile training ground where many notable comics earned their stripes.
“People get mad when we say this, but the best comedians come out of Chicago,” said Howery. “And the reason, I believe, is because of how segregated Chicago is. You have to know how to make so many different people laugh in this city, and not just Black people. Once you figure out that I can go to any spot in the city and make people laugh. … Chicago did this for me — I was able to be so confident coming to L.A. and going to New York because Chicago made me feel like a star already.”
Howery also gives a nod to a local legend on building confidence.
“Think about Bernie Mac,” he said. “For us Black comics, he set the tone for what being yourself looks like. And in Chicago we’re all comfortable in our own skin. That’s what makes us great comedians.”
These days, Howery lives in Los Angeles. But when he comes home, he likes to spend time in his old neighborhood.
“I like just driving up and down Madison. I did it yesterday. I do it every time I show up to Chicago,” he said. “It’s so many different parts of memories. If I drive to Western, I remember going to the laundromat on Saturdays with my mother, me and my brothers carrying our stuff. If I keep going further down, I see Providence St. Mel. My parents sacrificed to make sure I went to a better school. They didn’t even have it like that.”
He also makes a few unusual stops. Lately, he’s found himself stopping by the funeral home where his family held services when his father died.
“This gonna sound crazy,” he said. “I just wanted to stop there. I know he’s not there, but I built a relationship because I was there so much. You know how weird it is for me to just be there with some other people’s family?”
He continued: “I love what Chicago represents for me. I was driving up and down out west the other day and stopped to get some snowballs, and they was like, ‘Lil Rel what you doing on Central Park?’ And because they recognized me, I felt like I had to buy everybody snowballs, so I did.”
Howery has always maintained a close connection to the city, even after work took him away. When he filmed his sitcom, “Rel,” on FOX, the theme song was homegrown.
“One of my favorite songs is Crucial Conflict’s ‘In The Circle,’” he said, “because we all used to hang out in the circle, you know, on Madison and Central Park. It’s crazy, but I’m one of those lunatics. I said if I ever have a show that will be the theme song. So I had FOX call them, and pay them to remake it into a theme song.”
Looking forward to the festival, Howery said he’s eager for a chance to see the new crop of talented comedians.
“Chicago’s just a great place for standup comedy,” said Howery. “And not only standup. Like legendary sketch actors also come from Chicago. Every part of comedy, the best have come from here.”