When Donnell Rawlings and I connect by phone, he’s stoked to be chatting with High Times because the magazine holds a special place in his heart. “Years ago I was at The Stony Awards in New York with Charlie Murphy—may he rest in peace—and there was this one picture taken of us that showcased our friendship: I’m looking straight-faced and he’s laughing like shit. Whenever I think of High Times, I think of the ‘high times’ I had with my man, Charlie Murphy.”

Despite today’s “uncertain times” propagated by the coronavirus, Donnell remains optimistic about the future. “We’re going to get through this. It’s going to be a learning experience. People’s lives are going to be put into perspective and we have no choice but to grow from it.”

Over the course of our conversation, Donnell reveals how he’s used quarantine to channel energy into his podcast, “The Donnell Rawlings Show,” spend more time with his son, and most recently, become a fixture at “Dave Chappelle & Friends—An Intimate Socially Distanced Affair,” performing stand-up comedy for socially distanced crowds in Yellow Springs, Ohio. 

Seems like it’s all about finding the silver-lining in “negative” situations. 

Donnell Rawlings: You can’t appear to “enjoy” quarantine. Everyone’s so nervous to say anything positive about it, but there’s a factor—growth—that’s going to lead to people making better decisions in all parts of their lives. Health, family, love, business—everything. As much as people believe in God, they only believe in God when it comes to something good. No one understands what a curse from God is, and how you grow from it.

Let’s talk about growth but as it pertains to comedy. How did you get your start?

Donnell Rawlings: Growing up, I was a funny baby, a funny toddler, a funny teenager, and a funny adult. I’ve been funny in everything I’ve ever done. When I was younger, I didn’t have aspirations to be a comedian, but when I got out of the military, I was waiting to be a DC police officer and would go to this comedy club and heckle. I was an asshole heckler who only wanted to disrupt the show. Most hecklers want to pursue comedy but don’t have the balls to get up in front of people. They like to be in the shadows where there’s no pressure to be funny. In my case, I was a professional asshole. Nobody could fuck with me when I heckled. When I finally touched the mic for the first time, I caught a standing-O.

What gave you the courage to perform for that first time?

Donnell Rawlings: A six-pack of Colt 45 malt liquor and a joint. But I also wanted to challenge the people who thought I was going to fail.

Thefirst time I hit the stage, I knew I wanted to perform comedy for the rest of my life. It was exhilarating, it was energizing, and there was no turning back. I knew I wasn’t going to be a cop anymore, so I had to figure out a way to get fired from my job because I didn’t want to fuck up the oppotunity to collect unemployment. I needed that cushion to get my shit together and decide if I was going to move to New York.

When I first started, I never wanted to be famous. I didn’t think about fame, I didn’t think about money. The only thing I cared about was being good at stand-up. The only place I wanted to get respect was from the stage. That’s where I wanted people to connect with me. Anything in life, if you’re good at it, you’ll figure out a way to make money with it. You’ll figure out a way to meet the right people.

Hold up. How did you get yourself fired from your job?

Donnell Rawlings: I started to be unproductive. I was working security for this grocery store and there were times when there was an emergency in the store and I wouldn’t respond to it. I just wouldn’t pick my phone up. They were like, “Fuck that, we gotta get this guy outta here.” It worked in my favor and that was that.

So you move to New York, start comedy there. What was the path to “Chappelle’s Show?”

Donnell Rawlings: I left DC with an Air Force duffle bag, an alarm clock, and forty-dollars in my pocket and went to live with my friend in Brooklyn. I’d made a name for myself in DC and could’ve made somewhat of a living telling jokes there, but this was before social media where people could get to know you through a digital platform. The way people got to know you back then was through your reputation and people talking about you from the last city [you performed in]. I wasn’t established in New York outside of “I heard this guy’s funny,” so I had to start at the bottom of the totem pole and introduce myself to the clubs, producers and promoters.

It took me six to seven months before I started getting regular spots, and at the time, I was doing all Black shows. All urban shit, that’s what I connected with. Then, I had to make the crossover from the Black circuit to mainstream. The way you make that crossover is to be first and foremost funny, and then get referred by other comics to the more mainstream establishments. One day, I was in the stairwell of the Comedy Cellar, and I saw Barry Katz who represented Dave [Chapelle] at the time. I was like, “Barry, could you put in a word [with the Cellar]?” He was like, “Donnell, listen man. Just rip everywhere you go, and everything will fall into place.” And [while he didn’t make a call] he was right. I kept ripping and started getting passed at different clubs and people in the industry took a liking to me. 

I also started to have some success with acting and I’d booked a couple of episodes of “Law and Order” and was a regular on “The Ricki Lake Show” as an expert on relationships. Around that time, I auditioned for Neal Brennan, who was a talent scout for “In Living Color,” and he became a fan. Some time after that, he and Dave wrote “Half Baked,” and then went on to sell some other scripts. Neal wanted to get into directing, so he wrote a short script and reached out to my manager to see if I’d be part of it. I thought I was a big deal at the time, so I said, “Listen, I know you can’t afford me, but I’ll do this for you. If you’re ever in a situation where you can throw me a bone, do it,” which he was cool with. Some time after that, Neal hit me up about “Chappelle’s Show.” Although me and Chappelle had respect for each other and knew each other from DC, it was Neal Brennan who was the introduction to “Chappelle’s Show” for me.

Positive karma came full circle and Neal made good on his word.

Donnell Rawlings: People always assume I was on the show because of Dave, but that’s not the case. I’ll never stray from the reality that if it wasn’t for Neal Brennan, I would have never been part of “Chappelle’s Show.”

And as much as people want to say, “If it wasn’t for ‘Chappelle’s Show,’ where would you be?”— if it wasn’t for me, if it wasn’t for Charlie Murphy, Neal Brennan, the writers, production, craft services—that show would not have been what it was. Of course, Dave Chappelle is the name. Dave’s name is on the marquee. But producing a successful television show is a team sport. Nobody wins the championship just off of one person. What Dave and Neal did was they put together a championship quality team. Everyone was tuned in and on the same page to win a championship, and we did.

Let’s talk about cannabis. What role does it play in your life?

Donnell Rawlings: As cannabis loses its stigma, people are starting to understand all of its benefits. A friend of mine’s son is a kid with special needs and one of the only things that helped him with his seizures was cannabis. But he lived in a state where [weed] wasn’t legal, so my friend—who was a retired cop—had to break the law in order to get his son medicine that helped him live his life. I’m a supporter of cannabis—not just to get high—but for what it does for the economy, how it brings people together, it’s calming—it’s a whole bunch of things other than just the stoner image of Cheech & Chong.

I use weed as a tool in my creative process. I’m not dependent on it, but it definitely enhances my creativity. I mainly enjoy sativas because they open me up, and if I’m stuck with writer’s block, I’ll get a nice sativa-dominant hybrid. My favorite time to hit weed is early in the morning when I’m fresh and charged up. If I’ve got a bomb-ass sativa strain…man, my pen is flowing like Jay-Z.

Creatively then, does weed help inspire your material?

Donnell Rawlings: I’m an observational comic. For the most part, [inspiration] comes from the life I live, the things I see, and the conversations and encounters I have with people. That’s all the inspiration I need. Shit that I experience and see as funny, I bring to light.

The stage is an incredible outlet for me with regard to creativity. Because of COVID-19, I’ve been stifled from that live performance. But right now, I’m feeling so good about what I’m doing with “The Donnell Rawlings Show.” It’s my expression and it’s my brain, and it’s the one thing I’ve ever done in my career—other than stand-up—that I have one-hundred-percent creative control over. The name is “The Donnell Rawlings Show,” which means nobody can tell me to do shit. And as much as people call it a podcast, my idea of “The Donnell Rawlings Show” is that it’s a reality show about a podcast. It’s me not knowing if each episode will be well-received, but at the same time, I know that whatever I say, it’s authentic and true to who I am.

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