Chicago gave Lil Rel Howery a room before Hollywood gave him a stage. At 19, he found his first open mic by searching listings in the Chicago Sun-Times Weekend Plus, eventually landing at a small bar called the Lion’s Den. He does not remember whether he killed or bombed that night. What he remembers is getting through it.
“I was just happy that I went on stage,” Howery said. “I was just happy I went up there, did my time and got off.”
Years later, the comedian, actor, writer and producer is back home as the third annual What’s Funny Comedy Festival continues across Chicago through Sept. 26. On Sunday, Sept. 20, Howery taped his latest stand-up special at Black Ensemble Theater, adding another Chicago institution to the list of hometown venues where he has filmed his comedy. The taping was one piece of a festival that Howery says is ultimately about more than putting recognizable names on stages.
“We wanna make stars,” Howery said. “We wanna make stars and give opportunities. That’s what this is about.”
Howery is more involved in finding those stars than audiences may realize. He estimated that more than 200 comedians submitted for consideration this year, and said he personally watched every submission before comparing notes with longtime collaborator Knowledge Beckom and selecting performers. “I don’t know why people think that I just threw my name on that,” Howery said. “I watch every single submission.”
One comedian who immediately caught his attention was Baltimore comic Chi Chi. Howery said he called Beckom after watching her tape because something stood out. He later brought her in to open for him while headlining in Baltimore and came away even more impressed. For Howery, that discovery process is part of the fun, but it also reflects what he wants What’s Funny to become. He points to comedians who have participated in the festival and gone on to find representation, return to stand-up after stepping away or land opportunities in other projects. He has also brought festival talent into his own work and says he plans to continue creating new projects and opportunities in Chicago.
That investment does not necessarily come with an immediate financial reward. Howery said the festival has largely operated around the break-even point, sometimes requiring him to put his own money behind it even as sponsorship support grows. “We haven’t made a real profit or anything from it, honestly,” he said. “We kind of break even.”The response from his business team when festival season arrives has become something of a running joke, but Howery is clear about why he continues doing it.
“It’s my love letter to Chicago and my love letter to comedy.” Chicago remains central to how Howery understands his own career. When he eventually began traveling to Los Angeles and New York for showcases, people noticed how confidently he entered those rooms. From his perspective, he had already been tested by an audience that mattered deeply to him.
“Chicago made me feel like a star before I went to any other city,” he said. “It’s just time for letting the rest of y’all know what I can do.”That relationship with the city also helps explain why Howery continues bringing major moments in his stand-up career home. He has filmed several specials in Chicago and said the work has provided a way to return when a busy schedule might otherwise keep him away.
“I work a lot, so I don’t get a chance to come home often,” Howery said. “These specials have been like an easy way for me to come home.”
His decision to film at Black Ensemble Theater carried meaning beyond finding the right room. Howery spoke at length about founder Jackie Taylor, the theater she has sustained for decades and what he believes Chicago sometimes fails to do when discussing its own Black institutions.
“We just got to do a better job of talking about our historic landmarks and places, especially Black folk,” Howery said. For him, the larger question is not simply how to preserve those institutions, but how Chicago can build on what already exists. He talked about attracting major productions to Black Ensemble Theater while also creating work locally with the potential to move onto larger stages.
“We should have our own Black Broadway here,” he said.
That respect for the people and institutions that helped shape Black entertainment also shows up in the festival’s What’s Funny Icon Award. This year’s honoree is comedian and actor Bill Bellamy, whose career Howery believes deserves to be considered beyond stand-up alone.
“He opened up doors for a lot of us,” Howery said. “People really don’t give that brother enough credit of how important he has been, not only to the comedy culture, but to the hip-hop culture and to just the culture in general.”
For anyone who came of age watching Bellamy during his MTV years, the connection is easy to understand. Howery sees him as part of a generation of entertainers whose work moved comfortably between comedy, music and popular culture, creating visibility that later performers inherited.
Howery’s own entry into that world began much more modestly. The Lion’s Den may have once felt enormous to a 19-year-old walking onto a comedy stage for the first time, but Chicago eventually gave him something larger than a place to practice. It gave him the confidence to believe he belonged when bigger rooms opened.
He traces some of that belief even further back to his family. His mother died in 2009, and Howery lost his father earlier this year. When asked where his confidence comes from, he talked about a family that made sure he knew who he was long before audiences knew his name.
“They made a little nerdy dude with glasses think he was really dope my whole life,” he said.
That sense of self is also wrapped into what Howery considers a Chicago state of mind. To him, Chicago carries an honesty, work ethic and confidence that becomes particularly important when opportunity finally arrives.
“A Chicago mindset, like, no, I’m going to go get it once you let me in the door,” Howery said. “I’m not going backwards.”
More than two decades after finding that first open mic, Howery no longer needs Chicago to convince him that he belongs on the stage. What’s Funny gives him an opportunity to turn that relationship around by looking into the next room, watching the next tape and helping another comedian believe there may be a bigger stage waiting for them, too.