Published by the American Bar Association
The Dealmaker's Ten Commandments provides a practical, no-nonsense
Lil Rel Howery has a hard time listening. At first glance you’d assume it’s because he’s so engrossed in his mobile device, which the actor/comedian’s eyes have been squarely locked on since exiting his Lyft. As we try to make our way across the street, Rel is too focused on his text exchange to heed this journalist’s repeated warnings about the cars barreling down the block. In fact, he has to be pulled back on the curb at least twice to avoid getting hit by oncoming traffic.
Once safely upstairs and tucked away in a quiet breakout room at Complex’s Midtown Manhattan offices, it quickly becomes apparent that distractions aren’t the problem. Lil Rel just doesn’t make a habit of listening to anything that detracts from his own vision. So starting a conversation with a question about why a 38-year-old man, with a scene-stealing role in the 4x Oscar-nominated Get Out, would continue to bill himself as “Lil Rel” instead of something more “professional” immediately gets dismissed.
“People been tellin’ me to do that but nah, man—I’m not,” Rel says flatly. “The brand is what it is. The only thing I did was just add my last name, and that was my plan the whole time anyway—to make it ‘Lil Rel Howery.’ It’s a big thing about just being yourself. I never switch from whatever I thought people wanted to see; I been doin’ me this whole time and I believe that if you do you, people will create things for you.”
Blocking out detractors and speaking things into existence is a strategy that’s continued to work for Rel over the years. Born Milton Howery on the West Side of Chicago, he grew up watching shows like A Different World, In Living Color, and Saturday Night Live. Rel was drawn to the way his faves—including Kadeem Hardison, David Alan Grier, and Eddie Murphy—were able to make people laugh with their words and expressions, and quickly became “addicted” to the art of comedy. As with any vice, Rel eventually went to extremes to get his next fix.
“I think I was 13 or 14 when I bought Richard Pryor’s book, Pryor Convictions: And Other Life Sentences... I ain’t even gonna lie about it, I actually stole the book and ran home,” he recalls with a hearty chuckle. “But I read that and was just blown away. And then my father had a bunch of Richard Pryor albums, and I started listening to ’em. Then I saw [Eddie Murphy’s] Delirious for the first time, and that’s when I was sold. Eddie Murphy was just so funny. I was like, ‘That’s the style of comedy I’ma do. I’ma do characters.’”
While the seeds for Rel’s future career path were planted in that moment, his revelation didn’t fully manifest itself until his senior year at Crane Medical Prep High School. After doing a few church plays and expressing an interest in writing characters to his teachers, Rel got the opportunity to pen his own scenes for a school production. He killed the performance and won over his rowdy classmates, who were notorious for heckling everyone that hit the stage. Rel immediately became the man on campus and decided right then and there that he had found his true calling.
“I’ll never forget the moment of sitting in the dark by myself in the auditorium after the play,” Rel says. “That’s the moment when I told God, ‘This is what I wanna do.’ I don’t know how I’m gonna start, but I specifically said, ‘I wanna be a standup comic, actor, and a writer.’ And I just stared up there. Even though that sounds like this deep thing, I really did that. That’s exactly what I said out my mouth in that auditorium to myself. I’ll never forget that, because I didn’t know where to start. Nobody in my family did this. So it was just like, ‘Alright, we’ll figure it out.’”
Rel did more than figure it. Shortly after turning 20, he started hitting the local open mic circuit, including famed spots like The Lion’s Den and Riddles Comedy Club. The latter was a Chicago hot spot that was MC’d by future comedy star DeRay Davis, who gave Rel the opportunity to do a five-minute set every Sunday in exchange for helping seat patrons during the show. “I remember other comics giving me shit because I was seating people,” says Rel. “They were like, ‘Man, that’s degrading.’ But I’m like, I get the chance to go up at the hottest comedy club in Chicago every week; fuck you talkin’ bout?”
Once again, Rel’s penchant for not listening paid off. When DeRay made the move to LA to further his acting career it left his hosting gig at Riddles up for grabs. It wasn’t long before Rel, whose five-minute sets consistently had the crowd in stitches, stepped in to the vacant spot. After a few years at Riddles, Rel graduated to the city’s only Black-owned comedy club, Jokes and Notes, where he went from opening act to headliner before becoming the host of a weekly open mic. The Wednesday night show became so popular that it was common to see NBA and NFL players in the audience. As much as people came to have a good time and be seen, the real draw was Rel, who was quickly becoming known as the funniest cat in Chicago for his ability to roast people on the spot and create character-driven bits that were just as relatable as they were funny.
“Chicago made me a star first,” Rel says. “Because of Chicago, I ended up having the confidence to go... Like, I knew I could kill it anywhere. So when I used to come to LA [to do stand-up], they’d be like, ‘Dude, you’re up there goin’ crazy.’ I’m like, ‘I know. Chicago already made me feel like I was dope. So if I could make it there, I’m good.’”
By 2012, Lil Rel had racked up several national television appearances, including Comic View, The Bad Boys of Comedy, Bill Bellamy’s Who Got Jokes?, and Last Comic Standing, among others. But the gig that got him most excited was when comedy legend Keenen Ivory Wayans chose Rel to be part of the proposed reboot of In Living Color for Fox. The original sketch comedy series was a cult classic that was responsible for launching the careers of stars like Jamie Foxx, Jim Carrey, and Jennifer Lopez back in the early ’90s. So getting cast on the new series had the potential of turning Lil Rel into a household name.
“I told Keenen when I first met him that in my sophomore year, this was actually what I saw myself doing—I wanted to be a star on In Living Color,” says Rel. “So, for that to happen was just crazy to me.”
Unfortunately, the show wouldn’t be the vehicle that would propel Rel into the national spotlight. Although a pilot episode was shot, Fox announced at the top of 2013 that they had decided to cancel the series before it even aired. “The bar for In Living Color is so high that, if I didn’t feel like we could sustain that, then I did not want to move forward,” Keenenexplained in an interview with The Post. “I just feel like we’re in a different time.”
Despite the disappointing news, Rel was able to use the connections he made working on the show to land his big break on truTV’s sketch comedy show, Friends of the People. Not only would Rel appear on camera as a series regular, but he would also serve as a writer and executive producer of the show, which ran for two seasons before going off the air in 2015. Friends of the People may have had a short run but it provided Rel with valuable experience both in front of the camera and behind the scenes.
Meanwhile, Rel was continuing to develop his stand-up routine and eventually started catching the ear of Hollywood power players. The first was Kevin Hart, who backed the Chi Town native’s debut comedy special, Kevin Hart Presents Lil Rel: RELevent. Then there was Jerrod Carmichael, who cast Rel in his critically-acclaimed sitcom, The Carmichael Show. But the one who gave Rel his most impactful role was Jordan Peele, whose directorial debut Get Out really put the comedian on everyone’s radar.
Released in February 2017, Get Out was one of the first films of the Trump presidency to tackle race in a unique and impactful way. In addition to sparking a timely dialogue about blackness in America, the social thriller also got people talking about TSA Agent Rod Williams, the funny-as-hell character that represented the audience’s perspective as the voice of reason. Portrayed by Rel, Rod provided some much-needed comic relief as the horrific and emotionally-heavy plot unfolded. It was a small but memorable role that propelled Rel to the top of people’s search queries.
“What Get Out did was make people go research me, like, ‘Who is this dude?,’” he says. “After the movie my comedy special numbers went up on Netflix, and people started buyin’ it more on iTunes. I’m like, ‘Damn, I got one of the top-selling iTunes albums now?’ But it was based off of people asking, ‘Who is this dude?’”
Rel’s talent and on-screen presence was undeniable, and as the film got bigger so did awareness of its breakout star. “That little, small role [in Get Out] made me a movie star, but Jordan said it would,” says Rel. “After the first few cuts he saw, he texted me and was like, ‘Whatever you want, money-wise; they gotta pay you now. You about to be that next black movie star.’ I was like, ‘For real?’ But, yeah, he was right. I think the first time I realized what Rod meant to people was when I went to the premiere, and I walked out that theater and people were bum-rushing me, like, ‘Oh, my God, he was in the movie.’ That was the first time I realized that this was gonna get crazy.”
Get Out set the stage for a busy year for Rel. In addition to filming the third and final season of The Carmichael Show, he landed a recurring role on Issa Rae’s HBO hit Insecure as well as a cameo in Jay Z’s Friends-inspired music video for “Moonlight.” For some, it seemed like Rel had blown up overnight, but it was just all those years of grinding finally paying off.
“Nobody just appears out of nowhere if you put in the work and Rel’s been doing the work,” says Tiffany Haddish, Rel’s longtime friend and The Carmichael Show co-star. “What is it about last year? He did the work all the years before, that’s what he was doing. If you plant a fruit tree today you’re not gonna get no fruit from it for seven years. But you still have to water it, fertilize it, nurture it, and do the work to keep it alive. It always shocks me when people are like, ‘Oh, my god, this was the year.’ No, [he] had many years—you just didn’t know about it.”
In the wake of the Get Out buzz, Rel’s phone has been ringing non-stop. Some of the projects currently on his plate are Bird Box, a post-apocalyptic drama for Netflix starring Sandra Bullock and John Malkovich, and Brittany Runs a Marathon, an indie film about an underachiever who finally decides to take control of her life. There’s also Rel’s first leading role in this summer’s Uncle Drew, a basketball comedy inspired by NBA All-Star Kyrie Irving’slong-running Pepsi ad campaign. Rel plays Dax, a down-on-his-luck street baller who convinces Uncle Drew (Irving) to come out of retirement to help him win the Rucker Park tournament’s cash prize.
“Working on Uncle Drew was one of the greatest things I’ve done yet, ’cause I’m a big basketball fan,” says Rel, who also got to act alongside NBA greats like Reggie Miller, Chris Webber, and Shaquille O’Neal. “It was like being in a fantasy camp I paid for. Like Kyrie is amazing, man. That’s what surprised me, too. I didn’t know what I was gonna get, as far as actors, like, ‘Oh, I guess I’m gonna have to carry this movie.’ [Laughs] But they all were really good. It was surreal, man. I couldn’t believe I was working with them.”
That’s not the only Dream Team Rel is currently a part of. He and Jerrod Carmichael have joined forces once more to create a new comedy series for Fox. Loosely based on Rel’s life, the still untitled show follows a Chicago comedian trying to juggle his career, being a long-distance dad, and dating after finding out his wife was sleeping with his barber. Minus the cheating scandal, the show’s premise mirrors Rel’s real life pretty closely.
After several years of marriage, Rel and his ex-wife Verina finalized their divorce in 2016. Despite living apart the past four years, Rel, who now spends most of his time in LA, maintains an active role in the lives of the daughter, 8, and son, 7, he shares with Verina, as well as an infant son from a different relationship. “Nowadays, there’s no way you should be a deadbeat dad,” says the proud father of three. “You can at least FaceTime your kids. [Laughs] There’s no reason not to see your kids at all—no reason.”
While Rel has a good grip on co-parenting, he admits that being single and dating is something he’s still getting used to. “It’s tiring, especially since my position has changed—there’s a dollar sign [attached to my name], and I’m just like, ‘Yo, I can’t…’ I don’t wanna be out here no more,” he laughs. “Marriage is a beautiful thing, though. I would do it again in a heartbeat; I just don’t think you should get married at the age of 30. You gotta know exactly who you are by the time you say, ‘Alright, let’s combine these worlds, so that if we do bump heads, we’re gonna handle it maturely.’ But my ex-wife is dope; we’re still good friends. It’s a little annoying, because it’s like, how did we get cool afterwards? [Laughs]”
Sporting a color-blocked sweater, khaki pants, and a crisp pair of Air Jordan XII Retro Bordeaux, Lil Rel makes his way down the hall to Complex’s photo studio. Once there, he’s greeted by the photographer, who asks if Rel has a preference for mood music. “Anything ’90s hip-hop,” he replies. A few moments later the opening track to Nas’ 1994 opus Illmatic comes blaring through the speakers and Rel nods in approval.
As the album continues to play, Rel runs through the full gamut of poses in his arsenal—from the Birdman hand rub and classic mean mug to the more stoic and comical. The various looks are about more than just hamming it up for the camera, but representative of the type of range Rel wants to display as his career progresses. “The last few roles I’ve been playin’ these scenes, and I’m like, ‘Yes, yes! I get to show heart,’” he explains between shots. “One of the next movies I do I wanna do somethin’ where I get to do more heartfelt stuff. That’s why I love Robin Williams so much; he did a good job of mixin’ that up where he did funny, but he did stuff with heart in it, too.”
Once the shoot is wrapped, Rel hops right back on his phone, replying to texts and figuring out what’s next on his agenda. He’s got a full plate, but after praying to God all those years ago in his high school auditorium to be in this very position, Rel wouldn’t have it any other way.
“Chris Rock gave me some great advice about pacing yourself,” he says mid-text. “You don’t have to say yes to everything—and I try not to—but it just happened to be some of the things I’m saying yes to are things I already wanted to do, and people I wanted to work with. But I’ma make sure I pace myself, though. I don’t wanna burn myself out.”
Hopefully, Lil Rel will be able to listen to his own advice.