“I felt like a king,” Lil Rel says, still half-groggy in a suite at the Royal Sonesta on an unseasonably nippy August morning in his native Chicago. The night before he had taken the stage to do an hour of new stand-up comedy at the famed Chicago Theater with a king’s entrance, backed by pre-recorded chants of “Rel” that crescendoed to a deafening buzz, a reference to the rapper Lil Flip’s classic track “Game Over.” It didn’t take long for the audience to start chanting in unison at the bespectacled, 42-year-old returning hometown hero standing before them, clad in a red and black suit—an homage to his comedy GOAT Eddie Murphy as well as Bobby Brown, who he considers the king to “dark-skinned brothers” of a certain age: “I’m not even lying to you,” he says. “I googled Bobby Brown outfits. It was between three of them.” Rel tore the house down in his two back-to-back sold-out shows: Walking onstage for his second is when he had the realization that “none of these motherfuckers are better than me.”
His impetus for doing a special came from feeling left out. He felt constantly aware of the absence of his name in “the conversation.” From the social-media-prompt memes that only make room for a quadrant of faces when they ask who’s the best or who’s gotta go, to decidedly offline but still culturally relevant barbershop discussions, his name wasn’t coming up in the debate over Best Comic Out debate, despite a solid 15 years of working the comedy circuit before Get Out blew up his acting career. Or at least, his name wasn’t coming up often enough for his liking. “Motherfuckers forgot how they met me,” Rel says matter-of-factly, his voice reduced to a hoarse low register.
Rel (whose real name is Milton Howery, or “Terry” to his family to avoid confusion with the three other Miltons in it) delivered one hell of a reintroduction: The two shows were filmed and combined to create his new HBO special, I said it. Y’all thinking it, which debuted this morning on HBO Max. “You saw my full skill set [last night],” he asserts in the Sonesta, assessing his performance. “I’ve [never] displayed it in [my previous] specials. For some reason yesterday, that shit happened. Like how I can just make up a song on the spot,” he says, referencing a bit that hinges on a pitch-perfect Bone Thugs N Harmony impression, “or the ants.” (A top joke of the night, it paints success as just having a different, higher class of insect invading your house.) His previous HBO special, 2019’s Crenshaw, showcased his knack for telling fully-fleshed out, longform stories with multiple characters and payoffs, with almost 45 minutes dedicated to a family member’s funeral that he reluctantly paid for. But this new hour has everything from ripped-from-the-headlines jokes (about the reemergence of polio), to a first-person account of the moment Verzuz jumped the shark, to, yes, his take on The Slap.
Anyone watching Rel’s back-to-back tapings would be struck by just how much of his show is created in the moment. Televised specials are usually the end result of a comic painstakingly crafting and testing a set before audiences, making sure every punchline lands when the cameras roll. Rarely do comedians use valuable taping time to remove the safety net and just riff. And yet here was Rel, inspired by a random yell from an audience member to reference the Morgan Freeman-starring Black Movie Classic Lean on Me, and then digress into a full five-minute bit about the film, from impressions of some of the ridiculously intense characters to leading the crowd in a sing-a-long of the title song. “None of that shit was planned,” he proudly says about his many improvs. Rel commands the stage masterfully, but casually, with no hint of grandiose self-importance or self-doubt. It’s as if he just wandered into his family’s living room to find a full couch, so he decided he might as well entertain them. Decades of performing have given him the ease to craft fully developed jokes on a whim that keep the crowd roaring.
Rel’s a big believer in divine intervention. Every setback, in retrospect, has had a silver lining. Getting passed over in 2005 for a crucial slot on Diddy’s Bad Boys of Comedy HBO showcase led to him being free to accept an unsolicited offer from Jamie Foxx’s Laffapalooza festival the next day. Even being hit by a car early in his standup career ended up being beneficial by forcing him to hone and refine his act in ways that didn’t depend on physicality. Coming up, he regularly hit Chicago clubs like Jokes and Notes to put a comic spin on his feelings, no matter how heavy (he once performed an impromptu set that was all about selecting his mother’s funeral casket earlier in the day). All this has brought him to a place of extreme assuredness, to the point where he could tell the apprehensive execs at HBO that notes and overthinking will just dampen his product. “The last time I did that dumb shit, I failed,” he remembers, shaking his head. “It was for the NBC Diversity Standup Showcase finale. I remember getting all these fucking notes that I tried to [adhere to] and it ended up as one of the worst sets I’ve ever had. After that, I [just] had to find a comedy club. We went to Kym Whitley’s spot… I just needed somewhere to go up and just be me. Went up there and went apeshit on stage. Killed that shit. The producers of Last Comic Standing walk up to me outside like, ‘Hey, we saw you at the showcase. Why didn’t you do that?’ I was like, ‘They told me I shouldn’t do this.’ They said, ‘Don’t do that again.’”
Rel moved to LA in 2014, but he says, “I thank God Chicago is the city I came up in, in comedy,” Rel says now. “Because niggas is beast out here. So you had to really be fucking good.” When asked if he’s referring to the hallmark Second City theater, he says, “Man, fuck Second City. I’m talking about the Black side of comedy like George Willborn, Damon Williams, Marlon Mitchell, you know what I’m saying?” But as much as he bleeds Chicago standup, Rel can’t begrudge anyone who thinks of him as an actor first. After all, everything is playing out just as he and his agent orchestrated it after his scene-stealing, star-making turn as the comic-relief TSA officer in Get Out. (“Jordan [Peele] called me when he was editing it and said, ‘Man, when this comes out, just know your price.’”) He handpicked his many subsequent supporting roles after having a come-to-Jesus conversation with his rep about his goals and ambitions. His agent pulled out a book of upcoming projects, “and about ten of the movies you’ve seen me in [recently], that day we pointed the motherfuckers out. It was all on a sheet. It’s a weird-ass book I guess only the good agents got. It’s full of movies,” he laughs. “I was like, what the fuck is this?” Since then Rel’s avuncular, bespectacled visage has become inescapable and undefinable, whether he’s counseling Ben Affleck on getting cuckolded in the erotic drama Deep Water, backing up Ryan Reynolds in the action-comedy Free Guy, playing the prude to John Cena’s wild swinger in Vacation Friends, or serving as the stable married foil to Issa Rae and LaKeith Stanfield’s messy lovers in The Photograph. He can play the straight man or the jester, and he can even do a hint of menace, as proved by his cameo in Judas in the Black Messiah. “You see [comic actors] doing the same exact characters in every fucking movie. They keep doing whatever they think the audience wants to see them as. I never wanna be like that, that’s why I pick all these different movies.” His CV has allowed for a slow but steady allotment of reach, influence and recognition, showing Rel that the impossible isn’t so unattainable anymore. Like, say, walking down the street while visiting his home town with his kids last year and looking up at the historic Chicago Theater marquee he spent his life admiring and casually concluding that, yeah, he could probably sell it out now—which brought him to this triumphant night. (His family, he laughs, didn’t realize his star reached that high. “Terry’s that famous?” he says his uncle remarked when he saw the line of people stretching down the block to get the night before.)
In the relatively short five-year span since he rescued Daniel Kaluuya from racist body jumpers, Rel has gone from comedy journeyman to Hollywood fixture and inner-circle favorite, much like his pal Jerrod Carmichael, who gave him an early break with a role on his 2015 NBC sitcom The Carmichael Show. Now he gets messages from Adam Sandler praising Crenshaw, and invitations to ultra-private screenings of Black Panther with Ryan Coogler, Jay-Z, Beyoncé and Tina Knowles. Miss Tina now calls him or pre-records her vaulted pre-show prayers before he does a big gig. He’s got showbiz stories galore, like the time, while filming Deep Water, when he sensed that Ben Affleck and Jennifer Lopez would get back together before it actually happened. “He was giving advice [about navigating celebrity] to [Jacob Elordi] and the way he was talking about [his time with] J.Lo, and how [the media attention] was a lot for them, you could tell he still cared about her.’” Unlike a hilarious story about seeing a certain famous rapper snub Al Sharpton backstage, the Affleck anecdote didn’t make the new special…though there is an extended bit about 40-year-old guys trying to keep up when dating women almost half their age. Considering the pre-J. Lo relationship that Affleck hatched during Deep Water, it seems like that chunk could be Ben inspired, but the premise is actually more based on Rel’s own experience. Divorced from his wife of nine years back in 2017, Rel has given up the exhausting dating-divorced-dad life and is now happily Brady-Bunched up with a woman his own age, with her own four children to match Rel’s three. Embracing maturity is a big theme of the special, evident even in his sartorial choice, which is a pointed swerve from the fresh sweatsuit and Jordans he wore in Crenshaw, when he joked that he could finally afford the “90s drug dealer look” he always aspired to. Now, Rel is through cashing in on childhood dreams as he plots the next phase of his 15-year career. Step 1: Remind everyone that when it comes to comedy, he can’t be fucked with.
“I got so good at acting,” Rel says matter-of-factly. “That’s what made me do this big conglomerate comedy show because, how the fuck am I not in the conversation? I’m like, really good at comedy.” Inspired by Carmichael’s “fearless” Emmy-winning special Rothaniel, Rel took equal energy from other peers who he felt were talking out of turn, not naming names but not mincing words either. “They all talking shit about being better than [Eddie]. ‘Oh, I’ve done more specials.’ N-gga, but eight of them motherfuckers ain’t good. So, like, and?”
Rel does a few pointed Slap barbs that Chris Rock may or may not take a certain way. Rel—who has a relationship with Rock, citing a memorable heavy conversation they had, commiserating over divorce—shrugs off any static that may result. “That’s what stand-up is. It’s not about just talking shit or being defensive. I appreciate my friends because they just live in fearlessness. None of these niggas run shit. You know what I’m saying? I can say whatever I want to. What you gonna do?”
As for what comes after the new special, Rel expects his next projects to feature him even higher on the call sheet. The one-and-done season of his multi-cam throwback FOX sitcom Rel hasn’t dissuaded him from hatching a return to television that he promises will be “in a big way.” And working with Carmichael, who directed Crenshaw, is always in the cards, assuming he can find him. “I called him [recently] and he was in Greece. I said, ‘What the fuck you doing in Greece?’ and he said ‘What’s the point of being a rich n-gga if you can’t just fly to Greece for no reason?’”
But for now, consider his new special a notice to any naysayers, doubters, or those who had no idea he even was a stand-up. “I just watched how everybody else has been moving. No one treated shit like [the] big deal [it’s supposed to be] anymore. Everybody’s making their specials, they all look like the same shit. Sometimes they’re overproduced. I’m standing alone. I ain’t combining forces with nobody. It’s just me. The only people I look up to are Richard [Pryor], Eddie [Murphy] and Bernie [Mac]. And that’s why I showed a lot of Bernie last night. So think about that, right? You’ve got this fucking suit on. Those lights come up. The chants play. Who the fuck this n-gga think he is?” It’s Rel. Game over.
Photographs by Aaron Sinclair
Hair by Corey Hill
Grooming by Meagan Hester