When Milton Howery, Jr. was balling out on the court in high school, friends and family back home on the West Side of Chicago were reminded of his older cousin, Darrel, and nicknamed him as such. While Lil Rel had trouble getting out of his cousin’s shadow on the basketball court, he’s been able to carve out quite the career for himself in the comedy arena. From sold-out stand-up tours to beloved roles in The Carmichael Show and Jordan Peele’s Get Out, Lil Rel’s more than two-decade-long career has culminated in a number of coveted awards and now, his first HBO special.
The 90’s were spent studying the elites, from Eddie Murphy and Martin Lawrence to Louie Anderson. Instead of indulging in all of the tempting activities happening in the neighborhoods of West Side Chicago, Rel focused on perfecting his craft, even starring in the school play. That early validation he received from both teachers and his peers would eventually give Rel the confidence to continue performing and pursue his ultimate goal: to make the world laugh.
Lil Rel’s Live in Crenshaw special premiering on HBO is a dream come true for the veteran comedian. Directed by friend and collaborator Jerrod Carmichael, the special was celebrated with a screening and Q&A moderated by Terrence J at Neuehouse in Hollywood. Lil Rel arrived with his family in matching Crenshaw t-shirts, paying homage to the late Nipsey Hussle.
I caught up with Howery on the red carpet to discuss the making of his new standup special and the time we ran into each other at The Dime on Fairfax.
What are you most excited about as Live in Crenshaw hits HBO?
First of all, HBO is where some of the greatest comedians I’ve ever seen do specials. It still feels surreal, looking at the screen now. All my heroes in comedy have done HBO specials so to have one is so crazy. I’ve done all these movies and stuff but this feels like the biggest thing I’ve ever done.
Why did you decide to record this at Susan Miller Dorsey High School in Los Angeles?
You know, Jerrod Carmichael said he found a spot. He said “look, this is crazy, don’t get mad at me. I think you should shoot it in a gym.” I said “a gym? A gymnasium?” He said “yeah.” When we went to see Dorsey, as soon as I walked in, it just looked beautiful. Beautiful windows. He’s like, “we’re going to shoot it during the day, the sun will set at some point.” Bro, you’re brilliant. I told them “it’d be nice if we do it in the community, if we’re going to shoot it here.” To do it in the community, the energy was crazy.
I didn’t name it Live in Crenshaw until we were in the editing room. The first title was Live at Dorsey. They said we couldn’t say Dorsey because it’s a high school and I was cursing. So, legally I couldn’t do it, which was a blessing in disguise. “Can I say Live in Crenshaw?” Then, people said, “Crenshaw is not a place!” But the energy I felt in that room, the way Nipsey always described it — watching Boyz in the Hood, you see the description of what Crenshaw is. I felt that energy when I did the show, and that was the only way I could explain to people where I was. If I had said Baldwin Hills or anything else, you wouldn’t have understood. It just hits because it’s an experience. Crenshaw’s not a place, it’s an experience.
What did Nipsey mean to you? Did you know him?
I met Nipsey once. He was cool but it’s even bigger than that. It’s so funny, that’s why I wanted to do the special there because people were out here hurting. They were really messed up. Me and Jerrod talked about this like, “yo wouldn’t it be cool if we brought laughter to them?” Hopefully.
What did it mean to have your kids here?
Well, they’re consulting producers on the special. That’s why they’re here, they’re working. [Laughs] Nah, one of the reasons I went with HBO is because I wanted to make sure my kids had producer credits. They were there. They were actually at these tapings, giving their opinions on things. They’re 10 and 9, this is what they love to do. They love this stuff.
Were you intimidated at all by the students?
It wasn’t a bunch of students there, it was the neighborhood. It was people from the Crenshaw District there. Dorsey High School, Crenshaw High School, it was crazy. Once again, that’s why I named it Live in Crenshaw. It felt like I was in some type of rally. Like Dr. King could’ve went up after me — I felt like I was opening up for Dr. King. “Give it up for Martin Luther King!” [Laughs] That’s what it felt like.
Were you nervous at all?
Nah, which is weird. But I’ve been preparing for this my whole life.
How is your standup influenced by your own real-life experiences?
I tell true stories, stuff that’s based on my life, 99 percent of it is influenced by that. Characters that really existed.
How does performing stand-up in Chicago compare to LA?
You know what’s funny? I’m bout to say something real tough. I’ve been trying to explain community to people. A lot of people are the same everywhere. I mean, not like that. I think we all have the same struggle, same everything. Why was it so important for me to do it here? Because I could’ve done it in Chicago, but I wanted to prove to everybody that the community is a community. You understand? So it felt the same. It felt crazy, to be honest with you. It felt like I’m from there. They embraced me. I can’t wait for you all to see this, the energy was crazy.
What are your favorite venues in the city?
I love the Improv on Mondays at DeRay’s spot. Chocolate Sundaes at Laugh Factory. The Comedy Store is always going to be the Comedy Store. Actually, that’s where I love to watch comedy. I like to just pop in and sit there. Not going up, just watching.
What do you like to do on your day off?
I like to go to amusement parks with my kids.
I ran into you at The Dime recently. What do you like about that dive on Fairfax?
Let me tell you something, they might have to do a documentary on The Dime. They should write some type of dope, scripted… it’s really like a new Cheers. A new Cheers, but our Cheers. The hip-hop generation’s Cheers.