West Side comedian and actor Lil Rel Howery returned to Chicago on Sunday to film his newest stand-up special at the Black Ensemble Theater in Uptown as part of the What’s Funny Comedy Festival.
The week-long festival runs through Sept. 26 and brings comedians, performers and entertainment industry professionals to venues across Chicago. It features comedy showcases, headline performances, industry panels, networking events, live podcast recordings, content screenings and the annual Black Tie Brunch.
“It means a lot being born and raised in Chicago. This is where my roots are. This will be the fourth special I’ve shot here. It’s a love letter to my family, and honestly, it’s a love letter to Chicago, which is why we’re back again with the festival,” Howery said.
Howery added that he thinks Chicago has the best comedy audience in the world.
“My favorite part of performing for a Chicago crowd is really the energy. When you give them something to really laugh at, they’re going to laugh hard, and there’s nothing like a roaring Chicago crowd,” Howery said.
Family and faith have also played a role in Howery’s comedy. His uncle, Marshall Hatch, is a pastor at New Mount Pilgrim Missionary Baptist Church and inspired one of Howery’s comedy characters.
“Even with some of the feature films and other projects I’m working on, I’m practicing doing things with ownership in mind. Ownership is really important to me now,” Howery said.
After independently financing and co-directing “Rel Talk” during the 2024 festival and later licensing it to Tubi, Howery learned the value of the licensing process and the long-term benefits of owning his comedy content.
The festival was founded by entertainment executive Knowledge Beckom and Howery, who have worked together to build the event into a platform for comedians to perform, network and connect with entertainment industry professionals.
“Knowledge was my original manager for years. I wouldn’t be where I am without Knowledge. As the years have gone on, we’ve been trying to figure out something to do together, and this was the ideal. He’s one of the best, smartest businessmen I know,” Howery said. “I learned a lot from him as far as business goes, from the time I met him when I was 23 or 24 to where we are now. He’s a really smart businessman, and he’s so open-minded.”
Howery said he can throw out “crazy ideas” and that Beckom has always been open to them, which he believes has helped make their partnership successful.
One of Howery’s favorite parts of the festival has been watching comedians come together, laugh, network and share jokes with one another. Seeing those connections develop has been especially meaningful to him.
The special was filmed at the historic Black Ensemble Theater, a Chicago institution that is celebrating 50 years of using the arts to address racism and promote cultural understanding.
Howery praised Jackie Taylor, the founder of the Black Ensemble Theater, for her contributions to Chicago’s arts community and the legacy she has built through the theater.
“I’ll be the first special to be shot there. It just means a lot because Jackie Taylor, to me, what she’s accomplished historically has been amazing. That theater, along with her, deserves to be celebrated. That’s really one of the big reasons,” Howery said.
The theater also stood out for its production capabilities, with Howery’s team finding lighting, sound and other equipment already available in-house.
And though Howery filmed his latest standup special in Uptown, he still visited the neighborhood he grew up in.
“When I land in Chicago, I still take a drive down Madison. I go all the way to Oak Park, then I turn around on Jackson and go right back down. I’m so grateful to be from the West Side,” Howery said. “The West Side is where all my personality and energy came from. You can see it in my material.”