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Donnell Rawlings: From Underdog to Hitmaker in Comedy

Explore the comedic journey of Donnell Rawlings, from his breakout roles on 'The Wire' to unforgettable moments on 'Chappelle's Show' and 'Guy Code.'


Apr. 1 2024, Updated 2:32 p.m. ET

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Comedian and actor, Donnelll Rawlings' career has evolved since his early days on the HBO drama show The Wire and Comedy Central sketch comedy sitcoms Chappelle's Show and Guy Code. One of his iconic sayings was, "I'm rich, biaaaaatch," he appeared as Little Richard with his Jheri curl or Ashy Larry from the Chappelle Show.

Rawlings presents his versatility on sitcoms, and it has progressed to the point where he appeared on Snoop Dogg's F*cn Around Comedy Special.

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In November 2023, he performed at Funny Bone Comedy Club in Virginia Beach and was presented with his own Netflix special, co-produced by Dave Chappelle. He says his Netflix special is in a different boat than his previous comedic works within the last 32 years. He has been a road comic for 20 years but was thinking about working on a special when Dave Chappelle approached him with the idea during the pandemic.

"I was in Ohio, doing 50 shows during the pandemic, and every night, Dave Chappelle would say, Donnie, I want to produce your special. Now, I wasn't even thinking about doing a special, but I said okay, and we set a date," said Rawlings.

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Rawlings and Chappelle did the special and worked on the release date, but two weeks before the official date, Chappelle asked Rawlings if they could do the special again.

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"My response was why, and his response was I can put you in front of any audience every day of the week, and you'll rip it; it doesn't make it a great special. We have a lot of COVID-related jokes to protocol to get into the show; it will cut our audience from 700 to 300," said Rawlings. Chappelle felt I could work on the jokes; they could be better. "Two years later, we're in New York, and everything's on point, though. There's no COVID protocol, and I listened to him, did my homework, and I think we have a great special."

Rawlings is confident about the special based on longevity in the game, respecting Chappelle's counsel, and the subject matters mentioned in the special. For Rawlings, it's all about giving him the best and delivering jokes that stand the test of time. It's his extraordinary resume because everything started lining up for the comedian.

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"I think my experience and connections lined up for the Netflix special, and everything connected for the right time for my fans," said Rawlings.

Rawlings has been candid in his segments throughout his career, and the Netflix special was no exception. On the special, he talked about mental health, toxic relationships, co-parenting, being an older father, and other subjects that people can relate to regularly.

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Although Rawlings has been in the industry for a long time, his definition of comedy has stayed the same, especially for stand-up. Back then, you got on a stage with a microphone and performed in front of a live audience. But, nowadays, you can also entertain an audience through humor through social media. Although comedians generate a more substantial buzz through social media, Rawlings knows he is a true comedian. He knows that without followers and social media engagement, he can entertain a crowd immensely without wavering.

"Is it safe to say that I am the s***? Did it cross your mind with the right platform? It's light out, and if your answer is yes, then there you go; you see me grow and evolve as a comedian," said Rawlings.

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Rawlings knew he was on the trajectory to win in 2023, but when he did his Netflix special, he felt like the people following him since The Wire and The Corner; Rawlings has to give people what they want.

"Where I'm now, I've never been as successful. I've never made as much money as I'm making right now. I've never seen me moving to Dallas much, so right now, my special only validates who I am, and you'll know who I am, period, front and center," said Rawlings.

Outside of comedy, Rawlings delivers an ode to fatherhood but uses the acronym D.I.L.F. (Dedicated, Involved, Loving, Father) and uses the acronym to use words that people associate themselves with and switch it up.

The acronym reflects who he is as a father, and his son, Austen, is the greatest inspiration behind the slogan. Rawling says the acronym would only be launched with his son.

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"At one point, I thought fatherhood would bypass me; I thought I would be a super uncle and devote my time to my career. Then, when my son came along, he made me think differently," said Rawlings. "I realized that this is the purpose of my life, and he changed a lot of stuff that I was doing, a lot of stuff that I'm doing now. I realized there's something bigger than me, and I have something in my life right now that I get unconditional love."

Austen also expressed his aspirations in entertainment to Rawlings. Still, he informed his son about the importance of strong character, told him there would be people who would not believe in you or your talent, and overcame rejection because it's a rigorous industry.

Austen understood his father's reasoning but expressed that at eight, his dad inspired his desire to be in entertainment. It was such a massive moment for Rawlings because although he told his son that he must be built correctly to be in entertainment, Austen recognized him as an inspiration.

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"It doesn't matter what I'm going through mentally. Whether I am mad about the business, his mother, or anything else, once I see his face, it's like complete relief, " said Rawlings. "I want to give him more opportunity than my dad gave me, but for me, it's okay; it's like I get to start over; I'm building another me in the world, but better."

Rawlings said his goals are set for 2024 because he is winning, especially since he is releasing his Netflix special in February or March 2024. Rawlings has tunnel vision for 2025 and will continue to do stand-up for comedy lovers. As a veteran of comedy, he wants to make sure that he can have his name on the screen where people can watch him do stand-up. He says he doesn't need a small film or sitcom; that's it for him in a nutshell.

"All I want to do is go out and rip the stage in front of the audience, make my motherf****** money, and make sure my son is good; that's it because I'm already winning," said Rawlings.

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