Donnell Rawlings is a BEAST! With over three decades in the game, he’s established himself as a force to be reckoned with on stage and off. Throughout his career, his hard work and dedication to his craft have never wavered. As a result, he’s emerged as one of the hottest tickets in comedy in addition to being one of its most recognizable faces. He’s living proof that good things come to those who wait (and keep grinding!) Laser-focused on the future, Donnell is kicking off a new era with the debut of his first stand-up special, ‘A New Day,’ on February 27th for Netflix, produced by his long-time friend Dave Chappelle.
‘A New Day’ is one of four specials Chappelle is producing for Netflix, who stated, “I’ve been doing this a long time, and comedians like Donnell are not only friends but have inspired my own career. Anyone in the comedy community knows these names and knows their time to shine is long overdue. I am proud to be a part of this moment.” Donnell is unapologetic about the fact that although this is his first special – which was recently filmed during the New York Comedy Festival at the Hard Rock Hotel – it is actually the 3rd time Dave had him shoot it. However, good things come to those who wait, as Donnell is now at the top of his game. Over the past few years, Donnell has been opening for Dave on the road and destroying audiences worldwide. Dave was captivated and was sure Donnell’s new material would be timeless and exceeded everyone’s expectations to the level it is today.
Donnell initially captured industry attention with his comedic sketches as Ashy Larry on ‘Chappelle’s Show.’ However, his acclaimed role as Damien “Day-Day” Price on HBO’s ‘The Wire’ solidified his standing as a serious actor and propelled him into the theatrical world. More recently, he has impressed audiences with his role as Alvin in the STARZ TV series ‘BMF’ and his return in the second season, along with portraying the snarky Mr. Earl in Adam McKay’s HBO series ‘Winning Time: The Rise of The Lakers Dynasty.’ Beyond television, Donnell received acclaim for his role as Dez in Pixar’s blockbuster film, ‘Soul,’ earning him The Redd Foxx Award at The African-American Humor Awards in 2021. It’s an exciting time to be a fan of Donnell Rawlings, and the most important thing to remember is that he’s just getting warmed up!
Jason Price of Icon Vs. Icon recently caught up with Donnell Rawlings to discuss the evolution of his comedy career, the making of his debut comedy special, ‘A New Day,’ and the lessons learned along the way.
You’ve been hard at work in comedy for over three decades. How did your love for comedy first take hold?
I never really thought about becoming a comedian when I was young. The first thing I wanted to do was be an architect, but I wasn’t good at math, so I knew that wouldn’t work. Then I said, “Okay, maybe I will be a carpenter.” After I busted my thumb, I understood that wasn’t going to work either, so my path was the military. Like I said, I never thought about becoming a comedian. I always knew I was funny, but becoming a standup comic or actor was never my dream. It was just something that happened, and everything began to evolve. Becoming a standup led to the acting, and the acting led to me becoming a podcast host, which led to all of the other stuff. I was always a fan of comedy, but I never thought I would do it. I used to love listening to George Carlin and Richard Pryor, and there wasn’t a black comic in the world who wasn’t a fan of Eddie Murphy. However, everything that happened to me was just by chance, and I was in the right place at the right time!
Like you, I grew up in the DMV. Tell us a little about coming up in the comedy scene in Washington, DC.
Oh, man! I love it. The next time I come to town, it’s crabs, chicken wings, and Mambo Sauce for everybody! [laughs] Ya know, the comedy scene in DC was very competitive and a great place to learn because we had a lot of guys who had been doing it for a while. These were guys who paved the way for comedians to have integrity. The thing about DC comics was that we were adamant about being good and respecting the art. It wasn’t like it is today, where you hear, “Oh, can you roast?” We were all about getting the material, getting the timing together, being able to perform for anybody, and being true to the game.
What lessons did you learn early on that resonate as you advance in your career?
One of the biggest things I learned early on was to be original. You have to understand that it’s a job, regardless of what is going on in your personal life. One of my good friends and mentors was “The Fabulous Fat Doctor.” who passed away some years ago. He said, “When we do our job, we all have some heavy stuff on our shoulders. We’re all going through stuff, but when you step out on stage, you go out there to perform for the audience and make them feel good. You can pick up your problems and deal with them when you get off stage.
When do you feel you came into your own as a performer?
The first time I ever did standup, I got a standing ovation. That was partly because I was a heckler, and people wanted me to do it. When I finally did it, it was received well. However, I continue to be a work in progress. For some reason, after doing standup for 31 years, I feel like I came into my own with this new special, “A New Day.” When I say that, I think my timing was there. I’m usually a rapid-fire type of guy, which I was, but I felt like I took these people on a journey. I felt like I captivated the audience and that they were glued to their seats. I didn’t have to rush a joke. I was relaxed with it but still had high-powered energy. There was just something special about this special, especially after getting the criticism from Dave [Chappelle] and some advice he gave me. It made me realize how to be a good standup, which is one thing. You’ve got a lot of guys out there who are good standups and club acts, but the minute you turn that camera on, something disappears. With this special, I realized I could be chill and that my voice doesn’t always have to be loud. I could respect its joke-writing ability and ensure that every word counts and means something! I know it’s weird to hear someone say who has been doing it as long as I have, but I think “A New Day ” resonates so much with the title, music, and jokes. I feel like it’s a new day, and now it’s time for me to go to a different level. I’m trying to break the stratosphere now.
I just watched “A New Day” last night. I have to say that it truly captures the energy of seeing you in a small club. It sucks you in visually, as well as with the energy you bring to the stage.
Thank you! I’ll tell you another thing. I had been doing an arena tour with Dave, so my energy was big. Robbie Craw from Netflix said, “The most important thing is the first two minutes of your set.” If you’ve been following my career, you know how much energy I bring. The first thing I said was, “I’m feeling good!” You can tell I am feeling good. You can see it in my face and by how I was dressed. I said, “You know why I’m feeling good? Because I ain’t ashy no more…” That right there was the calling card! That one phrase was the calling card. It’s not just me saying it. People who know me look, and the first thing they say is, “Damn! He ain’t ashy no more!” [laughs]
It’s important to note that it’s been a long road for you when it comes to bringing ‘A New Day’ to life! Tell us a little about how it evolved along the way.
Dave [Chappelle] approached me about doing a special about three years ago, during the middle of the pandemic. I had been working with him in cornfields all year. He said he wanted to do a special, but it was tough to find a place because you couldn’t go anywhere, and we were dealing with everything Covid-related. Then, when things started lightening up, we chose this venue in Charlotte, The Fillmore, if I’m not mistaken. We lost half of our audience because, for some reason, be it not having vaccination cards or something like that. So, our backs were against the wall with that. However, I did do two shows. The first show, I killed it. Dave was a little upset about Netflix turning these people away and said, “Look, if we have to do it again, we’ll do it again.” I was like, “No! I need this money now! I need this show right now!” [laughs] The second show, I went out there and killed it again. I got a standing ovation. Then we announced that Earthquake and I would have specials coming out.
Maybe a week after we announced the specials, Dave called me and said he wanted to do it again. I was like, “What do you mean?” He said, “Donnell, I can put you in front of any audience, and you’ll destroy it, but that doesn’t make a great special. With all the specials I’m producing, because of your connection with me and ‘The Chappelle Show,’ yours is the most anticipated. If we’re gonna do this, we want something evergreen, classic, and something that feels that it can stand the test of time.” At the time, we had shots of people in the audience with Covid masks and everything. If we had put that in, as a viewer, you would have automatically thought about that time period. So, we had to revamp it.
About a year after that, we were doing some shows in Napa Valley. Dave records all of his shows. He asked one of his producers how many cameras we had for the weekend. The producer said that we had five. So, Dave looks at me and says, “Do you want to shoot your special?” I was like, “When?” Dave said, “Tomorrow!” I’m like, “Ohhhhhhhh!” [laughs] I had to buckle down for that, but I was really excited about doing it under the radar and without anybody knowing about it. Then, he said he wanted to do it again because he didn’t like the production.
I said, “What are we doing? You are the producer! What do you mean? You don’t like yourself?” He said, “Donnell, let’s just get this right!” There was some small stuff that would have been an oversight on my part, but I was like, “I don’t care, it was funny.” He said, “Well, people are walking around. People aren’t settled, and it looks a little restless.” But I knew I had ripped it! So, that was the second time. Then I was like, “I don’t know if this special will ever come out, but at least I got the money! Netflix, if you want your money back, you’re gonna have to sue me!” [laughs] That’s what I’m thinking! Then I had a date for the New York Comedy Festival, and I knew the venue was an untapped venue for standup. I knew it was a nice joint and that if we dressed it, it would be good. We decided to do it then, and that’s what we got what we have right now. I think the show evolved, and I evolved as a comedian. I learned how to make my jokes better and understood the flow and timing of it all, so the third time was definitely the charm!
What goes into getting yourself into the right headspace before you take the stage?
First, I clear my green room. I don’t like to have people around me before I go on. I like to turn the lights off, burn a candle, and get ready to go. I heard Jay-Z say a few years ago that as a performer, you should already be thinking about where you want to be on that stage before you ever get out there. So, the first show I did that night was good, but it still wasn’t what I wanted. As we approached the second show, I thought, “Okay, this time right here might be the last time.” I had to get into it, man. I had to have the mindset of “This is it. You’re not turning back. You’re not shooting it again, and you know what you’re doing!” Even in my preparation for this, I was saying, “I want my jokes to resonate. Word for word. I want everything to mean something.” It all came together, and we have a finished product that really feels special.
You open the special with “Feeling Good” by the legendary Nina Simone. When did you first connect with that song?
I’ve been a fan of Nina Simone for years. A few years back, I was just driving in my car and thinking, “What do I want? Do I want a fresh start? Do I want to forget some of my problems? Do I want to own the next day? What is the direct trajectory of my show?” It was tough for me to decide on that song. I say that because I am so used to coming out to high-powered songs, like French Montana, ya know what I’m saying? These fire songs! With this song, it brings a more theatrical feel to it. Like I said, I usually go up there to something high-energy, but with this special, I needed to go from ground zero, and I couldn’t get there without the help of music. When I perform, I use music to my advantage; I do call and response. With the special, I didn’t want to do that. I wanted the first joke to mean something. So, listening to the song and Nina Simone’s work really impacted me. For part of my career, I felt certain things weren’t happening in my career weren’t happening for certain reasons. That’s what connected me to her song, “Misunderstood.” However, “Feeling Good” connected me to what I was doing.
I started using it in arenas. When they introduce me in arenas, they say, “You’ve seen this guy on The Wire…” I get a couple of claps. “You’ve seen him in ‘Soul’…” I get a couple more claps. “But you fell in love with him as Ashy Larry on Chappelle’s Show…” and the people go ape shit, man! I had to go from the crowd going crazy to playing Nina to a whole stadium getting quiet and me starting over. When I bust that curtain, they go nuts! That’s what happened on this special as well!
You mentioned the suit you wore to shoot this special. What went into finding and incorporating the right look into your vision for the special?
That suit, and I have history. I had worn that jacket with a pair of black slacks, a white shirt, and some loafers, maybe three beforehand. When performed, it just popped. Everybody went crazy, but I didn’t want to do that again. So, I was like, “Let me do the whole suit!” That suit, man, the fit of it and the look of it was next level. I was like, “Maaaaaaaannnn!” Then I threw the red socks on for the pop of color. Nobody is doing that in standup right now! You’ve got Jimmy Carr and maybe a couple of others. Even people who wear suits don’t wear them like I did. I owned that suit, and I owned that look!
I couldn’t agree with you more. Another great example is how you included your relationship with your son, Austen. How has parenthood impacted you on a creative level?
Whenever people talk about their kids, they say, “Well, I’m more focused now.” I’ve always been focused, but now I’m looking at life through a different lens. In the past, I had a wide lens where I was looking at everything. Now, it’s like I’m using a finer lens. It’s that 50/50 lens. That lens that shows the detail. The detail is that I am here right now. My purpose in life was to make people feel good, take care of my immediate family, and do things for them. Now, my purpose in life is to make my son the best person he can be and give him the best opportunities I can. I feel that I was already evolving into a different level of maturity, but once you have a kid, it takes it to the next level, and that’s what Austen did for me.
I’m sure it has to be satisfying for you to look back on all the blood, sweat, and tears you put into bringing the special to the masses. What is your biggest takeaway from this experience?
My biggest takeaway goes back to what Dave said, “Great jokes don’t make a great special.” It’s about me getting more in touch with myself and not going for the easy jokes. I’ve got jokes on pop culture that I can just rip; it’s easy stuff. Then there is another thing that comics deal with: people stealing material. Certain jokes you can steal, but you can’t steal my life. So, it was important for me to get my life out there and talk about the things in my heart. If you look at this special, I think there is something for people of every age. There is something everyone can take from it. If it’s the Sexxy Red reference, the Taylor Swift reference, the mental health reference, or people dealing with co-parenting, I think I hit so many notes on that joint that a lot of people will be happy with it.
You mentioned your work as an actor. You’ve strung together a pretty impressive resume with some standout roles through the years. How have you most evolved in that realm?
On the acting side, I don’t think I’ve evolved as much as people think because I don’t work as an actor as often as people might think. I’m a horrible auditioner right now. I told my agents that I didn’t want to audition. I’m not being cocky, but I’ve been successful enough that I don’t have the pressure of making money through acting. So, when I do land an acting gig, it’s fun and great practice. I’d rather be a comedic star than an actor because, as an actor, someone else is always controlling your destiny. Unless you produce the films and put yourself in them, someone else must always approve of you or say you are that person. With standup, the only people who have to approve of me are the people who come to my shows. As long as these people pay money to get at me, they will! I do that when I look at the body of work, and, for the most part, every time I have had a role, people have told me I did a good job. In the last year or so, I thought, “What if you get a coach and take it more seriously? How can you position yourself.” So, now, I am gonna reintroduce myself to the acting world. But, if for some reason people don’t give me roles, I will either write my own stuff, or I’ll just tell jokes. That said, I want to give myself more opportunities for people to see what they like, and people like to see me act!
What do you look for in the material or projects you want to invest your time and energy?
It has to be something that feels good to me and that I would be proud of. I’m trying to find roles that go outside of my character. Early in my career, I was on every one of the Law & Order shows, but I was getting arrested in every episode. So, I didn’t want to be the guy who’d be like, “What did I do? What did I do?” as they cuffed me. I’m looking for parts that test me. You know, I’ve always kind of envisioned myself in a particular way. I’d much rather be comic relief in a dramatic series than be the funny guys in the funny series, if that makes sense. I like the challenge of not being just the silly guy. Even with “BMF” and “The Wire,” those were good roles that allowed me to play something I’m not. I’m looking for something that changes the audience’s perception of me as Donnell Rawlings, the funny guy.
What’s the biggest challenge you face as a standup comic in this day and age?
I don’t really have any challenges. I just stay the course. I say that because half the things going on I don’t take that seriously. I never subscribed to cancel culture because I won’t change or waiver from how I present comedy. I think cancel culture canceled itself by being so aggressive, anal, and serious about everything. Now, people are sick of it and are ready for people to speak their truth and say what they want to say. I don’t think I’ve had a lull in my career. Even back then, I felt as if it were a new day. I always felt that if a certain situation fell through, something else would happen as long as I stayed true to it. The biggest thing is that I still have fun doing comedy. I love it! I love the fact that when I come up with a couple of new jokes or premises, I can go up on stage that night and work it out. I am still in love with this, and I’m still a work in progress. I know I’m going back on this, but like I told you, I’m still a work in progress. All I have to do is continue to perform!
What do you consider the keys to longevity in comedy?
Being honest, being true to yourself, and getting on stage. You’ve gotta work out. There is no way you can take six or seven months off. To be a great standup comic, you have to stay actively involved. A lot of people wonder how Dave can keep turning out these specials, and it’s because Dave loves staying on the road. Even when he went on his hiatus, and people didn’t see him, he still showed up at comedy clubs. You’ve gotta love it. The key to the longevity of this is fuckin’ lovin’ it, man!
‘Chappelle’s Show’ recently turned 21 years old! It’s hard to believe two decades have passed since it hit the airwaves. What are your most vivid memories of that time period and bringing so many iconic moments to the masses?
There is no singular moment. It was just the camaraderie and the fact that we were doing something that nobody thought was as groundbreaking as I did. I think Dave and Neal [Brennan] were both frustrated because they had done so many pilots that had never been turned into anything. I think Dave would have just done standup forever if’ Chappelle’s Show’ had not popped off for him. I loved that it never felt like I was going to work. They trusted your comedic timing and sensibility. It was a healthy competition, and it was fun! We had so much fun. They could not have paid me for that show, and I would have still done it for three years! [laughs]
What about the show continues to resonate with audiences years later?
It was “we don’t give a fuck comedy!” [laughs] I think it speaks to so many people because we could do what we wanted. Comedy Central hated the Rick James sketch! They felt it was too long and that Charlie Murphy wasn’t funny. They were wrong as hell! [laughs] That ended up being one of the biggest sketches! Being on set was such a good time, and I had a blast coming to work every day. Most of the sketches I was in on the show were ones I wasn’t supposed to be in. It was just me hanging out because I didn’t have any money and wanted free food. I also knew Dave and them would say, “You want to get in this?” That was it!
Was there a moment when you realized what a phenomenon this show was becoming?
I knew it before Neal and Dave. They didn’t really get it. I knew that people had been fans of Dave’s for years, but real talk, the street, and the hood hadn’t caught on to Dave yet. When I was going to the barbershops in the “hood hood,” when I heard people talking about it, I knew it was something special. When the hood says it’s funny, it’s gonna be a banger!
‘A New Day’ drops on February 27th on Netflix. What are your short and long-term goals for the rest of 2024?
My short and long-term goals are the same — stay the path. I’m not greedy. Here’s what I’m excited about as a comic: I don’t have to wait for my phone to ring for dates. The fact that I can look at my calendar and it’s booked, for the most part, until 2025 is amazing! Everything after that is extra, bro! I’m being honest. I’m 46 years old. I’ve got all the ass I want to get off this shit. All that stuff is done, son! The fact that I can put my name on the marquee and make a nice amount of money was always my goal. It was never to be a TV or movie star. I want to be a dope ass comic, and that’s where I am right now, which will turn into something else. I’ll just see how it goes!
Are you planning to do anything special to celebrate the release of ‘A New Day’?
I think I will be in Yellow Springs, Ohio, chillin’ with a handful of people, just looking back and reflecting on all I’ve been through, where I am now, and where I’m about to go. I don’t need a big spectacle. Something nice and intimate is good enough for me because I still have work to do! I’m tellin’ you! After 31 years, I’m just getting started. First of all, you need the right platform for people to see you. I’ve been a beast on stage for years. Now, being on the biggest platform for standup, everything I’ve been feeling about myself, everything you’ve been feeling about me — This special is for you, man! It’s for the people who’ve fucked with me for years. I’m so honest when I say that. There’s people that used to come to shows and say, “Fuck, man! When is he gonna get a special? I love this guy.” That is who this special is for!
With that said, I have one more question for you. What’s the best lesson we can take from your journey so far?
Go hard or go home! That’s it. It’s that simple!
Donnell, you are living proof that hard work and dedication to your craft pay off! Thank you so much for the years of laughs and for your time today. I’m sure we will cross paths again soon!
Thank you, man. I appreciate it!
“Chappelle’s Home Team – Donnell Rawlings: A New Day” is set to premiere on February 27th on Netflix. It was directed by Emmy and Grammy award winner Stan Lathan and shot at the Hard Rock Hotel in New York City during the New York Comedy Festival.
For the latest news and tour dates, visit the official website of Donnell Rawlings at www.donnellrawlings.com.
Jason Price founded the mighty Icon Vs. Icon more than a decade ago. Along the way, he’s assembled an amazing group of like-minded individuals to spread the word on some of the most unique people and projects on the pop culture landscape.
