From Airman First-Classy to Ashy: Interview with Veteran Donnell Rawlings

An interview I conducted with veteran and comedian Donnell Rawlings originally published in Veterans Journal in June of 2011.

Joshua M. Patton
4 min readNov 3, 2022
Image via Pittsburgh Improv

“Can we please not do ‘Mr. Rawlings,” says the voice familiar as Ashy Larry to any fans of Chappelle’s Show, “I’d rather you say ‘Son’ or ‘My Dude.” Donnell Rawlings has been a comedian for many years before gaining national attention on Dave Chappelle’s short-lived but much-beloved show, but before he was a comedian he was an airman. As a child he initially wanted to be an architect but after learning about all the schooling involved, thought maybe carpentry was more up his alley. “But, I kept banging my thumb with the hammer, so that was done.” His brother was an academically gifted student whose guidance counselors pointed him toward the Ivy League, but when Rawlings met with those same counselors they pointed him towards the Army, Air Force, or Marines. He decided to take the ASVAB test because he would miss two classes and once he received his scores he enlisted at 17 and became a Law Enforcement Specialist in the United States Air Force. I mention to him that when I served in Bosnia, I thought the Air Force Security Forces were actually Special Forces at first, with their black berets and “SF” on their sleeve. “We would use any title to try and make ourselves seem tougher,” he says with a laugh.

Like all of us, his time in the military changed him on a fundamental level. Along with exposing him to culture that he wouldn’t have seen otherwise — including serving in Korea — he says the Air Force, “made me grow up as a man a lot faster,” than he might have otherwise. He’d always been a funny kid, but his wit and humor helped him through the tough times in the military. He looked younger than most of his peers and even though he was small, Rawlings says “I had a taller personality. My mouth was my M-16.” He left the Air Force after four years, but the lessons he learned there stayed with him as he began to pursue a career in comedy. From the Air Force, he learned discipline, respect for chain-of-command and proper protocol, and a sense of rank even in the entertainment business. Rather than see those with more experience as adversaries, he saw them as people from whom he could learn the business.

In a 2003 appearance on the now-defunct Tough Crowd with Colin Quinn, Mr. Raw — er, My Dude, came out strongly in support of the Iraq War. When I ask if time had changed his opinion, he reaffirmed his belief in the need “to make America safe from terrorism.” Only now, with both Bin Laden and Hussein dead, Rawlings wishes that the burden didn’t have to be carried by so many troops. “[Some people] listen to a Bruce Springsteen song and [they] listen to Lee Greenwood and are like ‘Let’s go get ‘em,’ but the reality doesn’t set in until you start having some casualties.”

In fact, Rawlings is looking to get involved in the USO and perform some shows from the troops based on the heavy veteran draw he receives when he performs stand-up in various cities. “When you say you’re prior service it’s like saying what college you went to,” he says, referring to the vets that come up to him after his shows. Like myself, they mention his work on Chappelle’s Show which unearthed some laughs at a time and a place where not much was funny. “It’s interesting to see how much that show had an effect on popular culture. People really loved that show,” he says wistfully.

I tell him about the firing of LTC Jenio and SGM Puckett and ask for his thoughts on the matter. “When it comes to comedy,” he says with the heaviness of someone who has dealt with comedic backlash, “people are overly sensitive. It’s usually one or two people making decisions for everybody.” He is no stranger to saying things that could offend, but he never tries to hurt people’s feelings. He cites a classic George Carlin bit where he disagrees with the notion that awful things, such as rape, can’t be funny. Carlin argues that anything can be funny, all it takes is one over-the-top exaggeration and a sense of context. Rawlings not only agrees with this, but takes it a step further, lambasting the idea of it being “too-soon” for a joke, “People might think it’s the wrong time the day after but in three months it’s okay? But I want to be the first one to do it, so I’m going right in on it.” I ask if other than hurt feelings are there any lines he won’t cross for a joke. “That’s a tough one, man,” he says, then after a moment of thought, “I don’t think there’s a place I won’t go for a joke, because the people who are real artists for the stuff can make anything sound funny. People need to lighten up, in general, and just laugh, man.” Rawlings’s special From Ashy to Classy is now available on Amazon and you can see him live by checking the schedule on



Joshua M. Patton

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