Fans of Chappelle’s Show may not know his name, but they definitely know who he is.

Whether they know Donnell Rawlings as the character Ashy Larry or for his quotable, “I’m rich, b*tch!” catchphrase that closed each show, he’s been making people laugh for decades.

If not from Chappelle’s Show, maybe you saw the Netflix special he did this year, A New Day, or remember his character Damien “Day-Day” Price on The Wire. 

Well, from Oct. 5-6, you can swing by Summit City Comedy Club to catch him live.

Taking a dare

Born in Washington, D.C., Rawlings grew up in Alexandria, Virginia, where he would go on to join the Air Force, where he was seeking guidance.

“When I was in the Air Force, my life goal was to not go to jail,” Rawlings said in a phone interview with Whatzup. “That was like, mission accomplished. 

“I really didn’t know what I wanted to do at that age. I knew I didn’t want to be walking the streets. I knew in the case of a lot of Black people, the military was a nice option if you weren’t going to go to college or had a nice skill. It was a way to make a transition to make a skill and be trained in something.”

While he did receive training and learned skills, it’s pretty safe to assume those were not in making people laugh. Instead, that was a talent he honed on his own.

However, being funny is one thing. Being paid to do it is another. He actually learned he could transition his humor into monetary gain in an unconventional way.

“I was funny, but I never thought I could do it in a sense of being a professional,” he said. “It started off as a dare. I would go to a comedy club and heckle comedians. The club owner wanted me to shut up. They challenged me to go on stage, and 30 years later, it’s what I’m continuing to do.”

Dual threat

While working on his craft at comedy clubs, Rawlings also took a stab at acting, where he found his first role where many actors do: Law & Order. He played the character of Etienne in a 1998 episode.

 “It was always about trying to be a comedian, but it was something where I was like, ‘Yo, let me see if I can do this,’ ” he said. “Early on in my career, I booked more roles as a dramatic actor than as a comedic actor. It wasn’t until I did Chappelle’s Show that people even knew I could be funny in front of the camera.”

Following his time on Chappelle’s Show, in which he appeared in 18 episodes, including playing Beautiful in the “The Playa Haters’ Club” sketch, his comedic timing was called upon more in Hollywood.

He’s appeared in the acclaimed comedies Black Dynamite and Black Jesus to name a couple, while also supplying the voice of Dez in the 2020 Pixar film Soul. He also appeared in the HBO series Winning Time: The Rise of the Lakers Dynasty and Starz hit show BMF.

Showing he can get it done in front the camera, it’s stand-up that he falls back on and what he’s constantly working on.

“Before this (A New Day) dropped, I was already 30 minutes into a new one,” he said about the work he puts into stand-up sets. “That’s a constant thing. I do more road work than anything, so I never want to cheat my audience by doing the same jokes. 

“I’m pretty sure I’m one of the few comics to take it that serious. I know a lot of comics say, ‘I know what’s going to make them laugh and I’m going get this check.’ I really pride myself on making these people become fans of me, not just for one show, but for life.”

Fortunate

When he makes his stop in Fort Wayne, he enjoys to get out, saying he’s a foodie and likes to mingle with folks. And if you happen to mention some of the characters or catchphrases that have become part of pop culture, he won’t be upset with you.

“I understand how hard it is to be recognized or known for anything in this business,” he said. “I look at all the thousands and thousands of comics that haven’t appeared in a show that are known for something. 

“I don’t take myself that seriously. Ashy Larry is kind of like art imitating life — I do struggle with ashiness. So, if anything, if it can be true to my life, why not make some money off of it? Buy a ticket to Donnell Rawlings, Ashy Larry, Alvin — I don’t give a hoot. Just get the dag-on ticket.”

According to Rawlings, there’s plenty of occupations out there that are worse than telling jokes, and he’s grateful for where he is.

“At the end of the day, I just look at it like this: What I do for a living is something a lot of people love to do,” he said. “Everybody has a God-given talent. But can you identify with it and make it work for you? I’ve been able to do that. That’s why I say I can’t take myself too serious: I tell jokes for a living!

“I walk through the streets of New York hearing (making construction sounds). 

“I look at these people and say (to myself), ‘You’re lucky that you have this life and opportunity to meet new people, make people feel good, and create a good lifestyle. How can you lose?”

And what do those people on the streets yell at him when they see him? 

“They be like, ‘I’m rich b*tch! Ashy Larry,’ ” he said with a laugh.