'Chappelle's Show' Co-Creator Neal Brennan Talks About His Off-Broadway Show, Mixing Comedy with Emotion, and Dave

Neal Brennan has, on the low, become like a "sun never sets on him" kind of entertainer. He's the kind of comic who's always on TV somewhere, even though you may not realize it. He's the voice of Samsung's phone ads that run through every big game—and it seems like there's a new ad every week—he's the director of Nike ads, and he's the co-creator of Chappelle's Show, which, thankfully, keeps popping up on Comedy Central all the time.

I know Neal, and the annoying thing about his success is that he's such a nice guy that you can't help but root for him. He was Scottie Pippen to Chappelle's Jordan on a championship team that won two titles—season one and season two—but his comedy in the years since then has shown he's a really funny guy in his own right. His stand-up shows and his podcast The Champs and his work directing Amy Schumer's show all make it clear how funny he is, and sometimes he gives off a glimpse of how smart he is, too. Neal's next big step is bringing his one man play 3 Mics to New York, playing off-Broadway at the Lynn Redgrave Theater from February 23 through March 13. I called him recently and asked him some questions about it.

VICE: So how do you explain the concept?
Neal Brennan: The concept is three mics onstage, spaced equally distant from one another. One is for stand-up, one is for one-liners, like things I couldn't put with anything else, and one is for true emotional confessions or short, emotional stories.

This is not a normal comedy show. It's not what you would do at a Caroline's. It's more emotional and deeper and broader. When I would do podcasts, I would have just as many people say, "Hey, you were really funny," as people who would say, "Hey, that thing you said about depression really helped me." And I've also seen friends go on Howard Stern or any of the shows and get emotional, and it's so much more interesting to me than just watching them be funny. I'm not going to say the market is flooded, but there are a lot of people doing comedy.

So why do this show then?
I had to say to myself, "What do I have to offer that other people may not have to offer?" I can think conceptually, and I have emotional depth that I can explain in a way other people can't. The reason why you see so many comedians at the top of the podcast list is that we can talk about stuff in a way that's compelling, even if it's not funny.

One thing you say a lot in your comedy is "If I were black…" How did you get to this place where you seem to have more racial empathy? Where does that come from in you?
I think early exposure to hip-hop and Spike [Lee]'s movies. I mean, I just find the whole thing so absurdly wrong. Like, the whole thing. Racism and slavery. This is so not right, and it's so obvious and clear that it's not right. And then it's proximity. Most of racism is based on a lack of exposure. Once you're exposed to people, you're like, "Oh, I get it." Like, I've seen white people touch Dave's hair. And I'm like, "Ugh." I'm sure no one's ever touched your gorgeous hair, Touré. But I've just seen the inconvenience of race. Can't get a cab. Guess what that means—you're going to be late. Stuff like that… Dave used to say he would move slower around white people so as not to alarm them. He was almost explaining it to me in a lot of ways.

How did your friendship with Dave start?
The Boston comedy club. I dropped out of NYU, and we were like the only young guys. Me and him and Jay Mohr, who was young, like 18, 19. I gave Dave a tag for a joke, and his initial response was to shudder at someone giving him a tag because it's a little aggravating if you don't know the person. I was like, "Hey, maybe say this part after you're done with the joke…" At first he was like, "Ugh." But then he heard what I said and was like, "Oh, that could work." Then he tried it, and I think it worked.

What was the hardest part of working with him?
How many more of these questions you got? Did he die? Is there something you need to tell me? Is this going to turn into a profile piece on Dave's life?

[Laughs]
Uh, yeah. Tardiness. That was the hardest thing with him.

That show gave you a ton of street cred. I bet you can probably go into almost any hood and say, "Hey, I made Chappelle's Show," and they'll be like, "Oh, let him through."
The best version of that ever was about ten years ago. I was with my girlfriend at the time who is mixed, and we were walking on 125th Street [in Harlem], and I could just feel these dudes staring at me and her. Like, Who's this motherfucker with a black girl? And we get close to them, and one of them goes, "Oh, shit. It's Neal!" And I didn't know the guys at all but all was forgiven. It was so goddamn funny to me.

So that show raked in a lot money, and you were a co-creator. Do you have to work now?
That's a tough question to answer. It's hard to say. It depends on how long I live, I guess.

Fair enough, but right now are you in a super comfortable position?
Yes. But I made money last year doing Samsung voiceovers. I directed a Nike commercial. That was a nine-day shoot.

Which one?
It's called "Fast." It was the dopest shit I've ever done in my life. It was Kobe, Serena, Richard Sherman, and they're all talking about how fast they are. I got to write it. I had [David] Fincher's DP as my DP—Jeff Cronenweth. The most accomplished DP I've ever worked with. He did Fight Club. And he is, of course, the easiest and most accommodating DP I've ever worked with. It was a dream come true.

So are you going to become a director?
I can direct. I've directed a ton of spots in the last year, but I would like to be a comedian. The story of 3 Mics is the story of a guy who wants to be something and is sort of figuring out how he gets there.

When you reach that point that you don't have to work for money, does that artistically free you?
So many comedians are filthy rich now that the idea that it affects your work is just a thing that no one talks about. Kevin Hart grossed $100 million last year on the road—more than U2 and the Rolling Stones.

I'm not suggesting there's a lack of grit when you get to that point. I'm wondering, do you get freed and liberated to where you're like, "If they don't laugh, I'm still good, so I'll tell whatever joke I really want to?"
No. It still stings when they don't laugh. It stings. There's nothing worse than trying to be funny and not being funny. I think Conan was on some podcast talking about when he does a wedding toast, he's scared. The fear of public speaking is a primal fear. You can train your body to not be crazy when you're doing it, but it truly is a primal fear. Look, all money does is take a worry off of your list, but what you find is you have a general threshold, a general level of worry, and it gets filled up with other shit. So it's not, "Oh, I can relax." Instead, you just worry about other stuff. It's like you always have a certain amount of worry that you'll spend every day. You worry about the same amount about different stuff.

How did you become Mr. Samsung?
Somebody dropped out, and they needed someone the next day, and I went in and did it. That was for the LeBron one, where they were comparing the iPhone and the Samsung. And I just added this thing where I said LeBron's literally running away from his phone, and they liked my voice, which I didn't expect them to. I think they were like, "Oh, he's decent and can occasionally add something"?

It's a great job.
Oh, dude, trust me. I don't have to shower—it's like a mile from my house. I can bring my dog and shit.

You're on TV all the time with that. How often do they have you going in there and recording stuff?
Not that much. Maybe every other month.

And the sessions last how long?
Two hours.

So how do you create a new stand-up show? The creative process of a comedian is a total mystery to me. I have no idea about how one goes about writing a joke.
It's hand-to-hand. I have a show every Sunday that I do, and I spend Sunday afternoons writing, and it's based on things I've written in my phone. I look at it and try to cobble shit together.

You've been taking notes throughout the week.