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For comedian Donnell Rawlings, doing stand-up with Martin Lawrence a ‘bucket list’ opportunity

The “Chappelle’s Show” alum, coming to Chicago with the LIT AF Tour, continues to stay busy with an ever-growing list of acting and performance gigs.

Donnell Rawlings performs in New York in 2017.
Jason Kempin/Getty Images

Since the end of “Chappelle’s Show” in 2006, comedian Donnell Rawlings has stayed busy over the years.

Rawlings, known as Ashy Larry and other characters on the hit Comedy Central series, calls his upcoming appearance on Martin Lawrence’s LIT AF Tour 2021 (Oct. 23 at the Credit Union 1 Arena) the chance of a lifetime.

“When I found out that it was an opportunity to tour with Martin — in my area of comedy — it’s almost one of those bucket-list things you want,” said Rawlings. “You either want to act with Martin or share the stage with him. When I started, he was the first comic I saw that I said, ‘This dude is talking about all the things I do.’ It’s so simple, and he just makes it look easy. [Lawrence] was the first person who inspired me to do what I want to do.”

Rawlings will appear on the tour’s Chicago stop with comedians Earthquake, B. Simone, and Benji Brown — an opportunity to put things in perspective, he says.

“I just can’t rely on large performances [always happening],” said Rawlings. “But one thing as a comedian who has been doing this as long as I’ve been doing it, you can book your calendar a year out; you’re pretty confident that you’ll be good. But [COVID-19] made me put things in perspective. You got to have other avenues to be able to support yourself. Nobody wants to see money go out with no money coming in. And then also it really made me realize how overrated Hollywood is at this point in my career.

“When I first started to be seen, you had to be in Hollywood. Now with social media and people doing a lot of things, you can create Hollywood wherever you are.”

Rawlings says he loves Chicago — except for the winters.

“I’ve been coming to Chicago for years,” said Rawlings. “Chicago has always treated me right. I love the spring and summer in Chicago. Y’all can have the winters [laughs]. I used to do shows with Deon Cole out there. I’m excited to come back years later and to be on a tour that’s hosted by one of the dopest comedy minds in the business.”

The Washington, D.C. native’s first live performance during the COVID-19 pandemic was last month, opening for old friend Dave Chappelle at Milwaukee’s Summerfest. And like all content creators, he too had to pivot in the midst of the gig economy.

“Every comic is saying: ‘What am I going to do for money? What I am going to do for stage time?’ Dave called me up and he said: ‘I got an idea. I want to do a show in a cornfield,’ ” said Rawlings. “To that, I said: ‘What strain of weed he smoking?’ Because I didn’t know how excited people will be about doing the show in the middle of a cornfield.’ But this summer turned out to be probably the best experience of my career. Getting in touch with nature, being able to hang out with friends, and being able to do three or four sets a night.

“I know COVID was not good for a lot of people, but for me, it was a game-changer and it was a life-changer in so many ways.”

Rawlings points to his work on “Chappelle’s Show” and the cult hit HBO series “The Wire” — along with his appearances on the Showtime documentary “B---hin’: The Sound and Fury of Rick James,” the new STARZ series “BMF” and the upcoming HBO limited series detailing the 1980s “Showtime” era of the Lakers as proof of success.

“Not to brag or anything — and I’m not a superstar by no means — but my resume is kind of dope [laughs],” said Rawlings. “I think Entertainment Weekly and one of the publications did a Top 50 to 100 shows in the history of television, and ‘The Wire’ and ‘Chappelle’s Show’ both made the list. I say myself: ‘If that isn’t history enough to a career, I don’t know what is.’

“For 25 years, I’ve constantly been able to have somewhat of an impact on television, and more importantly, an impact on stand-up [comedy] in general.”