Interview: Talking To Donnell Rawlings About His Special, “A New Day”

Donnell Rawlings’ new special - A New Day - is a culmination of 30 years in the stand-up game. For anyone who has ever seen Donnell onstage, you know just what he can do to an audience. Hitting the stage these days in a well-dressed suit, those who have never seen Rawlings won’t know what hit them. The energy he brings to stand-up has to be experienced live.

A question every comedian asks themselves when they’re taping a special is “How can we replicate what it’s like to see me in a club for a special?” Rawlings found a way, thanks to his friend and longtime collaborator, Dave Chappelle. Chappelle - who produced the special - went as far as encouraging Rawlings to tape the special three times before it was ready. Why? Because he knew what he was capable of onstage. And that needed to be captured in the final product.

It paid off. When you see the special, you can get a strong sense of what it’s like to see Rawlings kill onstage in comedy clubs, theaters, and arenas all over the country. Regardless of where you’ll see his stand-up, you’re guaranteed to have a good time. That comes across in A New Day. 

We recently talked to Rawlings about his new special that’s out now, how he felt like it got better, asking Snoop Dogg to be in his Netflix special, and the importance of a good tailored suit.

Tell me about the genesis of getting to this special.

Well, there’s a 30 year career. But I was doing shows with Dave Chappelle in the cornfield of Ohio during the pandemic, and we were working with each other every day. And out of nowhere, he was like “Please let me produce your special.” I never asked him to do it. He suggested it that he’d do it. And right close to the tail end of the pandemic, we went for it. We did it in Charlotte, North Carolina. I got a standing ovation. Chest bump with Ricky Hughes. And I was like “We have it.” And we were gonna start doing press for it.

And once we announced that the special was going to come out, maybe a week after that Dave called me and said “I want to do it again.” And I was a little confused because how can I go from this excitement to you want to do it again? To which he said “You know Donell, you’re one of the funniest guys I know. I could put you in front of any audience and you would destroy the room. But that doesn’t necessarily make it a great special.” I was like “What do you mean?” “Well, there’s a lot of COVID material in there. It’s a little dated. I’ve seen you do some of your jokes better. If we’re gonna do this - especially since my special is the most anticipated one out of the group of the Home Team - let’s just knock it out of the park.” And I was like “Okay.”

And then maybe a year after that, we were doing some shows in Napa Valley. And Dave records all of his shows. And he asks one of the producers “How many cameras do we have?” And she said “Five.” Dave said “Donnell, do you want to shoot your special?” “When?” “Tomorrow.” No time to prep or anything. I’m like “Why not?” So we took a stab at that. I thought that was a successful special. We got a standing ovation.

A week after that, he was like “I want to do it again. I didn’t like the production.” I’m like “You are the producer. What do you mean? You don’t like yourself? This doesn’t make any sense.” So back to the drawing board a second time. I was part of the New York Comedy Festival last year. I was very overwhelmed. I didn’t know when we could schedule it to do it again. So I said “Why don’t we just bring the cameras in to shoot it?” We came in. I think the jokes evolved. I understood what he was saying. I did my homework. I accepted the constructive criticism.

And I think at that moment, that night, I was at the top of my game. It made me respect his decision as an executive producer. It made me respect him as someone who has won all these Grammy’s and everything. I was like “Let’s do it your way with MY way also.” And I think we got a good product. And I really believe there’s something that resonates as a special. I look good, the jokes were good, the set looked good. And I think there was just a truthful energy that went through it. A guy that’s telling jokes about yourself, not taking yourself too seriously, not subscribing to cancel culture. And someone who’s unfiltered, unedited, and funny.

It sounds like you’re grateful now that you got to tape it again. Because that’s not something that generally happens.

My good friend Jeff Ross said that never happens. In fact, Dave had put his money up every go-around. But that just shows his commitment to our friendship. Whenever you tell a comedian you don’t want to put something out, his pride is freaked. Because you think “Was it not funny? What did I do?” And every time he said “Donnell, it had nothing to do with you. The first time - because of all the COVID restrictions - we lost half of our audience. And then the other half of them had masks on. If we dropped that special today, it would’ve took you back to 2020.

You saw the special. I think aside from a couple of jokes that are topical, I think this special would’ve been funny five years before now, and I think it will continue to be funny five years afterwards. 

The other thing you did so well in the special is you captured your energy. I saw you twice live and I watched you kill both times. I know how hard it is to replicate that feeling, but you did.

It’s so funny you said that, because you have a special where you’re in the room and you watch it and you’re like “Oh my god. This person killed it.” That doesn’t mean it translates to TV. It doesn’t mean it translates to people watching it. When I did the special in New York, the thing that I was more excited about wasn’t the people watching in the audience, it was the people that were watching it in the video village. It was the people in the screening room. If I can captivate that audience, then that’s going to come off on TV.

And I have had so many sets where I’ve killed. But the thing is in that moment, can you step up to the plate? A lot of times when the lights hit, people buckle up. They talk themselves down. I didn’t do any of that. I got what I think Dave wanted, I got what I wanted, and I think I got what the people wanted.

Do you approach comedy any differently if you’re playing a club versus a theater versus an arena?

It never changes. But I do also notice a different type of timing. This special, I could’ve done it in front of 5,000 people. But where I thrive the most is comedy clubs. So I said I wanted to do something that felt like a regular weekend. When you do an arena, you have to slow down a little bit because there’s a wave of laughs. You have to wait for them to clear out. At a comedy club, I can hear the distinct laughs. So the energy that I put into it isn’t any different from a club to an arena. But it’s a little bit more precise.

In fact, I’d been touring with Dave doing arenas for like five or six months. So in that, I had big energy. I was playing it as if I was in front of thousands and thousands of people.

What is the bit in the special that took the longest to come together?

What I had to do in the special was condense a lot of jokes. A lot of those jokes - if I’m doing an hour - I can just stretch them out. For this special, I wanted to trim all the fat off. I wanted everything to be a bit I could close on. I know my voice is distinct. I was very, very particular about this. I said “Every word has to count. I can’t have no wasted words. Everything has to be a setup.” If a person makes a transcript of that set, you could read it and it would be just as funny as if you actually watched it. So I tried to be able to catch all that stuff and it came off that way.

I’ll tell you one of my favorite moments from when I saw you live didn’t wind up in the special, and that was the bit you did about the song WAP.

Yeah, because I dropped that on Snoop Dogg’s. Snoop Dogg’s special came out of nowhere. I saw him post about the special. One comedian after the next. And I was like “How do those guys keep missing me?” And I told my people “I want to be on that special.” Everybody tried everything. Then someone said “Donnell, Snoop Dogg is in your phone.” So I called Snoop and said “Hey I want to be part of it.” He gave me the black fist pump and he gave me a thumbs up. The next day, I got a call from my agent. They said “We got you Snoop Dogg.” I’m like “Get the fuck out of here. Y’all didn’t give me that shit. Snoop gave me that shit.”

That joke was of the moment. The song was popular. For that brand and for what Snoop was doing, it was perfect. It’s something that I don’t even do anymore because it was a time sensitive thing. For that moment, it was a perfect thing.

Yeah, I get that. The song is four years old after all.

But I think I do a good job at explaining it. I do sell it. But I wanted eliminate myself of that and try to get some stuff that’s evergreen.

Jumping around all over the place, I wanna bring up a mutual friend that we have, and that’s Kevin Smith.

Aw man. I love him! Hollyweed! Don’t even say it, bro!

I was gonna say. I wish that pilot had been picked up. It was so good.

It was. What happened was the thing that separated it was there were two partners. They didn’t see eye to eye. They’re beefing. That had so much range. So much potential. People loved it, Snoop loved it. I thought it was going to come back, but then the company - the start-up - it fell apart. And that was the end of it.

Well hopefully you and Kevin can do something else. I know you’ve been in a few movies of his.

That dude’s so awesome. I know he’s a huge fan, man.

Now I read in an interview that the first time you went onstage you got a standing ovation. Did that spoil it for you? Because it’s not always gonna be like that. 

No, it didn’t spoil me. But one of the reasons why it was such a thing was because I had been going to this club for like a month heckling comedians. And everybody - all of my friends - everybody wanted me to do it. Everybody wanted it to be the birth of a comic. They were like “It’s time for you to graduate.” So I didn’t think there were any well written jokes or anything. One of the reasons was because the energy was there. Like “Oh man. He’s on his way.” And to this day, I’ve always been the person like “Okay, this joke can get better. I can try harder. I can add something.” Until I die, I will continue to be a work in progress.

But that built my confidence knowing that I could stand in front of an audience and I can grab that mic and I can engage people and make people laugh. I probably just roasted the audience. I probably did one joke I thought I wrote. But it was just building my confidence and getting out of the gate. It was the birth of Donnell Rawlings. It was the birth of a 32 year career.

How long did it take you to start develop an act after that?

The crazy thing is, at an early age, I talked about me being a security guard in a grocery store which developed this street character out of that. I was developing bits and characters right out of the gate. When I first started, I had been doing comedy for six months and nobody could believe it. They thought I had two or three years of time in. When I did my first TV show, Def Comedy Jam, I had made that after doing comedy for six months.

That also never happens.

In that case, it happened to two people. Me and Tracy Morgan. Because when we first started, people were like “Donnell. You’re like the DC Tracy Morgan, and Tracy Morgan’s like the New York Donnell.”

Well that’s great then that you had all that momentum going so if you ever did have a bad night, you could brush it off and keep going back up.

Yeah, but I never had too many bad shows. I think just something about when I started. It’s like Martin Lawrence. Martin Lawrence is so likable that it would be hard for him to do a bad show. It might be something where he forgot a joke or like he was in the dark, they couldn’t hear him. But certain people are just not able to not be funny. They look funny, they act funny. And with the material, they’re gonna catch up.

Part of your overall look onstage is being very well-dressed. When did that come together?

That was like two years ago. One of my friends from Brooklyn, we had just reconnected. He was like “Have you ever had a tailored suit?” I was like “No.” And he had this tailor and was like “I have these people that want to make you a suit. They’ll give you $500 to post it.” I was like “Fuck this suit. Give me the money.” But I was like “Why not?” The first time that I got a tailored suit, I put it on and I was like “Oooh.” I felt like respected. As a comic, I always just wanted to be comfortable. Nice sneakers and jeans and a t-shirt. I just wanted to be comfortable.

I thought wearing a suit would restrict me and my mannerisms. But once I got it, I was like “Maybe I need to learn how to walk in a suit and how to carry myself.” But I embraced it. And then the response has been really good. And also, you get funnier every year. But what can you do to get to the next level? Well, the way people look at me. And that’s what that was.

It’s almost like an added joke in itself.

Man, Robbie Praw from Netflix said “The most important part is the first two minutes of your set. That’s what catches the audience.” When I come out - and people haven’t seen me like that - and I say “You know why I feel good? Because I’m not ashy no more,” it’s like lights out.

And what’s next for you? Are you working on a new hour?

Right now I’m a half hour into a new - I don’t want to say special - set. Because now I have to go travel and do other stuff. And I’m also developing a show - a sitcom if you want to say - that’s sort of about what happen when I did my transition of moving from Hollywood to Yellow Springs. But I’m not getting ahead of myself. What I want to do is get the best material I can and then be as funny as I can onstage. And if that gives me more opportunities, it’ll give me opportunities. One thing is for sure. People can continue to see me go onstage at these clubs and make them laugh.