Comedian Donnell Rawlings has come a long way since Ashy Larry

July 2024 · 5 minute read

After two decades of being known as “Ashy Larry” from “Chappelle’s Show,” Donnell Rawlings says he’s gone from “ashy to classy.” These days, the 56-year-old stand-up comic and actor from Alexandria rocks a tailored suit with a pocket square onstage, where his unmistakably boisterous voice and expressive eyes bolster the hard-hitting jokes audiences have loved throughout his career.

Rawlings is eager to share his latest material with his hometown crowd at the Howard Theatre on Sunday, just days after Tuesday’s premiere of his first solo Netflix special, “Donnell Rawlings: A New Day.” With those famous Nina Simone lyrics as his mantra, Rawlings says he’s “feeling good” about his set, in which he satirizes “therapy speak,” co-parenting and traveling while Black in New Zealand. “A New Day” is the third installment in a series of specials executive produced by Rawlings’s friend and longtime collaborator Dave Chappelle.

Rawlings, known for his roles as Damien “Day-Day” Price on HBO’s “The Wire” and Alvin on the Starz show “BMF,” says he learned what made his special special when Chappelle made him rework his routine before giving his stamp of approval.

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“Two years ago, we shot a special in North Carolina where I got a standing ovation,” Rawlings told The Post. “A month before deciding if it was going to air, Dave pulled it. He said, ‘I could put you in front of an audience and you’ll destroy the room, but it doesn’t make it a great special.’ I had to listen to this little constructive criticism, not get in my feelings and understand what he was saying.”

In response to questions sent through his publicist, Chappelle simply says, “I’ve known Donnell for decades and have always enjoyed working with him. He’s one of the most earnest comedians I’ve ever met.”

Rawlings says his fellow D.C. comics, like Chappelle and Earthquake, whom he met through the city’s comedy scene, have helped him avoid gimmicky acts and form a lasting connection with audiences who wouldn’t see him as a “flash in the pan.”

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“Twenty years ago, I would have felt like I needed a special for people to be introduced to who I am,” he says. “But with this, I feel like people are rooting for me.”

Rawlings spoke with The Post about the pressure to deliver laughs in D.C., moving from Hollywood to Ohio and how he stays rich with opportunity.

This interview has been edited for clarity and length.

Q: You were deemed a breakout star of “Chappelle’s Show.” Your fans assumed that when the “Chappelle’s Home Team” series of specials was announced, yours would be the first. What took so long for your Netflix special to come to fruition?

A: You can’t rush it. Things happen when they’re supposed to happen. I just had to continue to position myself where Netflix would consider giving me an opportunity. You’ll make yourself go crazy being upset about when was the right time. The time I was able to do the special was the perfect time for me.

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Q: What do you and Chappelle bring out of each other creatively?

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A: Staying true to the artistry of what we do. Not just giving in to trends. We push each other. It’s a very, very healthy competition. Dave sees me do a set. I might get a standing O. I know that’s going to make him want to give it his all. Same thing with me and Earthquake. We went on tour together last year, and we alternated who would close the show. We push each other to be great. It’s no days off when we work with each other.

Q: You’ve compared your style to the late Robin Harris. How did he inspire you?

A: Robin seemed like the uncle that everybody wants to hang out with. He could roast you, he could do a stock joke, he could improvise. If you go to a family reunion, everybody has one story that the entire family knows, but it’s only one person that you want to hear tell that story, and that was Robin Harris. In my family, it’s me.

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Q: What’s it like performing for your hometown crowd?

A: I do an annual show at the DC Improv for Thanksgiving weekend, and it’s one of my toughest ones because you’re not just performing for an audience but you’re performing for your aunt, your uncle, your classmates. You’ve got to be so truthful because these guys know your history. I always feel a little pressure when I come to D.C.

Q: During the pandemic, you moved from Los Angeles to Yellow Springs, Ohio, where Chappelle is also based. Why make such a drastic change?

A: I realized Hollywood is overrated. You can create a good lifestyle for yourself not being there. So I went from the streets to the creeks and from the hoods to the woods. I made the transition from Adidas to Tevas, and I found some sense of peace.

Q: And now you’re coming back home. What can Washingtonians expect from your show?

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A: Dave said, “If you want to see a comic, come and check him out after he’s filmed a special because now it’s a new process.” It literally is “a new day.” I can’t use those jokes I used in the special. I’ve got to go deeper. This is a time when comics really test their armor. After dropping a special on Netflix, I know people are like, “What can he come with now?”

Q: The Post did a piece for Black History Month about 14 meaningful Black D.C. landmarks. Is there one of particular significance to you?

A: I’m excited about doing the Howard Theatre. Back in the day, I grew up listening to go-go music, and it was one of the hottest spots to have a good time. I have so many memories of dope musicians and performers there. So for me to be able to go back to relive those days and be connected with that history — I’m excited about that. And I plan on tearing the house down.

If you go

Donnell Rawlings Live at the Howard Theatre

The Howard Theatre, 620 T St. NW. thehowardtheatre.com.

Date: March 3 at 7:30 p.m.

Prices: $40-$80.

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