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Comedian Donnell Rawlings Talks About Chappelle’s Show and Being a Stand-Up Dad

Allen Zaki
Comedian Donnell Rawlings performs this weekend at the Addison Improv, but you've also seen him before on TV and movies.
Comedy Central's Chappelle's Show and HBO's The Wire are two shows that often get mentioned in lists and analyses about programs that changed the course of television. Comedian Donnell Rawlings is an important part of both of them.

He played characters like Ashy Larry and helped shape sketches like “Black Gallagher” on Chappelle's Show hosted by Dave Chappelle. The show started discussions on uncomfortable subjects through comedy. The Wire, created by David Simon, was a crime drama depicting both sides of America's never-ending drug war with an uncanny attention to detail and brutal, unapologetic honesty.

"It's easy for me to talk about it," Rawlings says referring to fans who recognize him from the shows. "I see the excitement when they talk about it. There's always a good story attached to it.

Even with a long list of acting roles, Rawlings is still touring with his stand-up, including five shows this weekend at the Addison Improv. He’s been featured on just about every major comedy stage a comedian can hope for like Just for Laughs and the upcoming Netflix is a Joke: The Festival. Rawlings has also filmed comedy specials for television and streaming channels Amazon and Netflix and built an impressive list of roles in shows and movies. Some of his most recent performances include parts in Pixar's Soul and in the HBO sports chronicle Winning Time: The Rise of the Lakers Dynasty helmed by Oscar winning director Adam McKay.

"It makes me look at it like this: I'm a part of history, and after 27 years of the relationships I've built, it makes me want to make my own history," Rawlings says. "I'm being more empowered to put my own Winning Time together." Even with such an accomplished career in competitive show business, Rawlings branched out to producing his own podcast and serving as the senior content advisor to the Vyre Network streaming app.

"I wanna be the mac in the back," he says. "With my 27 years of experience, I feel like I'm starting all over."

It's impressive to imagine just what Rawlings wants to build and create given the steps he's made to get there starting with his time on Chappelle's Show — as have other names who built new phases of their careers on the groundbreaking comedy series.

"It was just a lot of people who played in the league for a long time like Michele Armour, Bobcat Goldthwait, Rusty Cundiff," Rawlings says. "When it came together, it was just electric. "

Rawlings makes an impressive presence on the screen no matter how much time he gets. He worked on Chappelle's Show as the announcer and a regular cast member with electrifying characters like the appropriately named Ashy Larry and the Jheri-curled "playa hater" Beautiful, which he also got to revisit when Chappelle hosted Saturday Night Live in 2016. He says he even helped create some of the show's most memorable moments starting with "Black Gallagher" in which Chappelle plays a version of the fruit-smashing comedian.

"For some reason, I said this motherfucker looks like David Chappelle," Rawlings says. "David Chappelle is a black Gallagher. That's all I said. Other times, I took hours to do a pitch but this was just one goddamn sentence. It taught me a lesson, like keep it short, sweet and trim the fat off of it."

Rawlings also played a small but crucial dramatic role in Simon's The Wire as Damien "Day-Day" Prince, an aide and driver for corrupt Maryland Sen. Clay Davis played by Isiah Whitlock Jr. Rawlings' part singlehandedly introduces the influence that politics can have on law enforcement efforts, especially when it comes to money.

"Originally on The Wire, the role of Omar [played by Michael Kenneth Williams] came down to me and Mike for Omar," Rawlings says. "Then the Baltimore tourism board came down and it went from the towers to the docks in one season. When that happened, the character got lost and I was so ready for it.

"I don't know how important a role is at the time but I do know what's important is for me to kill it," Rawlings says with a laugh. "I consider myself the Busta Rhymes of acting. You don't see me do a lot of albums. I'll come in here, I'll spit out 16 and I'll move. I never look at it like I'm never gonna have another scene or I'm never gonna have another job. Do the best you can when you have it.

"When people see you for the first time, they gotta go nuts. I did not know I was going to be Ashy Larry until the day before. I blew that dust out and the place went ape shit."

No matter what's next for Rawlings, he says his "biggest accomplishment" is becoming a father to his 6-year-old son Austen who, Rawlings says, is developing his own ear and voice for comedy.

"He would try to be funny at my expense," Rawlings says about his son, who recently appeared on his podcast. "Yeah, roast anybody, but your father, motherfucker? He was answering a question and paying attention. My son could be a natural, and I'm not forcing it by any means, but when I say I'm going to work, he knows what I'm doing.

"Becoming a father really makes me realize why I do everything that I do," Rawlings says. "Every year has been good. Every year, it feels like it gets better. I love it so much that I never feel like that's the best I can do."