Talking to Neal Brennan About ‘Chappelle’s Show’, Standup, Podcasts and More

Much in the way that Bill Clinton was considered our first black president, Neal Brennan might be our first black podcast host.

As co-host of The Champs podcast, along with comedians Moshe Kasher and DJ Douggpound, Brennan brings the predominantly white podcast universe a much-needed dose of diversity through his show’s edict of having only black entertainers as guests. It’s a funny and interesting formula that works, as the podcast is edging towards 1 million downloads. And what better ambassador to the black community, as Brennan himself would probably tell you. He earned his street cred co-creating Chappelle’s Show, one of the most successful black-themed television shows of all time.

After years spent behind the scenes working on Chappelle’s Show, writing screenplays and directing the studio comedy The Goods, Brennan shifted his focus to performing and has since become a successful touring stand-up comic. He’s appeared on late night television shows, headlined clubs across the country, and last month, hosted his own weeklong showcase at the Montreal Just For Laughs Festival.

I got the chance to sit down with Brennan while he was in Montreal to talk about his podcast, his love for stand-up, and a dope ass mixtape he’s putting out soon.

Off the bat, I got one Chappelle’s Show question, and this is more of a theory I have…

Everybody’s got one. You ain’t shit if you don’t have a Chappelle’s Show theory.

[Laughs.] No, this isn’t even about Chappelle’s Show specifically. Can there ever be another hugely successful sketch show now that we’re in the YouTube era where millions of sketches are available online?

We were pre-YouTube. Even the idea of making money from DVDs, it’s never going to happen again. Because I see the money I get from streaming, and it’s like “ugh.” It’s like Splitsider money. It’s like I’m writing for Splitsider.


But yeah, I think you’re probably right in terms of consistent heat from sketches. I feel like Lonely Island is kind of doing it. They did their “Dick-in-a-Box,” in fact when they were doing “Dick-in-a-Box,” Timberlake said this would be such a Chappelle’s Show sketch. It’s basically “Piss on You,” you know what I mean? It’s the same kind of premise. Yeah, you may be right. Everything is “it will never happen again until it happens again.” If you’re talking about water cooler shit, there are elements of that, because when it aired you had to watch it and you had to get the DVD. There probably is something different about that experience than there is about people watching stuff online and sharing it.

I think people still want story, and will watch things that have a story, like Breaking Bad or Mad Men. Without a story, it seems like people are thinking, “Well, I could watch this, but at the same time I could just get on my computer and watch a million cat videos or guys-falling-over videos or whatever.” It’s more difficult to hold people’s attention.

Absolutely. You know what’s funny? Chappelle’s actually said that. He was talking about Moore’s Law and how there’s so much shit now that he actually says that will probably never happen again. I completely forgot about that. There’s so much noise. It’s really hard to make something where people are really fixated. But like I said, a couple of those Lonely Island sketches…

Can you make money on those online sketches?

Those guys make money off endorsements and commercials and shit. They have a vodka affiliation. That didn’t exist during Chappelle’s Show. There was no, “Come host a party and get 50 grand!” It just didn’t exist. So they’re making money in different ways.

So why did you get into stand-up and how long have you been doing it?

I did a little during Chappelle’s Show, but I realized you gotta do it every night. I’d do it and then take four months off to write. I was doing it during Chappelle’s Show, and then Dave left, and I didn’t want to do it anymore because I felt like people were like, “Where’s Dave?” What I realized is show business is constantly telling you you’re not funny, so it’s nice to go somewhere just to remind yourself, “No, I am. I swear I’m funny!” And I like that all I have to do is rely on myself. I don’t have to rely on Dave. I directed that Jeremy Piven movie, The Goods, and the president got fired from the studio after we made it, then a new one comes in and he sits on it, and then Jeremy has the sushi thing. Just stuff where you’re like “Motherfucker!” Just these happenstance things that affect me personally that I have no control over.

The Goods didn’t do well. You’ll never know why. Maybe it was me, maybe it was Jeremy, maybe it was the writing, maybe it was the cast, maybe it was the studio, maybe it was the date it came out. The forensics is so bad that you just never know. The thing about stand-up is it is the fairest genre of show business. It is mostly meritocratic. That appeals to me, even though it took me a while to get as good as my peers because I had a late start.

Yeah, were you just thrown into the clubs? You got to skip the whole open mic process.

Yeah, which was great. But I wasn’t headlining or anything. That’s what was cool about it. People would tell me, “You should do a Neal Brennan and Friends or something.” And I was like, “Eh, I’d rather just wait till I have an hour.” I started having an hour about a year ago, and I’ve been going out, and it’s been great. And I feel like I’m not ripping people off. I’m not like “Hey, remember? Rick James!” I’m just doing stand-up, whether you’ve seen Chappelle’s Show or not…So yeah, I like the autonomy of it. I don’t mind relying on myself, you know? I make door deals at clubs where I’ll come in for a night and if people show up, I get a percentage of the door. If they don’t, fuck it. Don’t worry about it. I’ll bet on myself. I don’t want to rip people off; I just want shit to be fair. If people show up, I want to get money from them. If they don’t, then I don’t get any money. And also, it’s really immediate. If I write a joke today for my act, I’ll do it tonight. If I wrote a joke for a movie, I’ll find out if it works in a year and a half.

Do you feel like you got an early education hanging around comedy clubs with your brother while you were growing up? Did you pick up on certain things about how to be a performer?

Yeah, unwittingly. You know what I picked up on more was writing. I remember hanging out with my brother and Dave Attell in New York because those guys were best friends and then I’d go back and hang out with my friends and one of us would say something funny and be like, “I wrote that.” And we’d be like, “No, I wrote that.” Meanwhile, we’re just high school kids. We’re not writing; we’re just being idiots. That’s probably the biggest advantage. Because you don’t even really think about what it takes to be a performer until you start performing, at least I didn’t. Eventually I learned, “Oh, I need to be commanding and forceful.” And now I have sort of an agenda when I go on. The audience can tell if you don’t have the chops, you don’t have the presence. Just doing my show up (in Montreal), I’ve seen people with chops go up and be great, and then others who just don’t have it not do as well.

No matter the material.

Doesn’t matter. Just doesn’t matter. They can tell. It’s like, “We have to listen to this guy or not.” And that’s just time. I may have cheated it a bit by really focusing on it and setting goals for myself performance-wise, without shame. I think some people approach it like, “Yeah just go up and do whatever.” Even guys I know like Bill Burr will try to do a new thing like, “Alright, I’m going to take the mic out of the stand now.” He tries a new thing every year that he’s never done. I have no shame about being methodical about process. I remember being 18 and having a comedy book about writing comedy and it was hiding under my bed and Chappelle saw it and said, “Oh, I’ve read that book.” He’s read tons of books on comedy. A guy who seems like the most naturally gifted comic in the world, and he is, but also he went to theater school, and he’s read books. Some guys get into stand-up to smoke weed and play videogames. You’re not going to do that well. You have to have a real method.

What’s been the hardest thing for you coming in as a writer to learn about performing?

Smiling on stage. Literally, smiling on stage. Being engaging. Not being smug. Just things you don’t think about as a writer where you’re scowling all day. You can’t be scowling. These jokes might come from a place where you’re scowling, but they won’t work on stage if you’re scowling. You’re just going to seem like an asshole. So yeah, that stuff, and being more open emotionally. It’s just stuff that you may learn in theater or acting class. I had to learn projection and I took a voice class. Like I asked Dane (Cook) what he did? His first record doesn’t sound anything like his second record. So I asked him and he said, “I took voice lessons.” The more you open your instrument, the more commanding you are. If you can be like that on stage in front of people, they’re like “Wow, he’s not nervous at all.” It’s like neuro-linguistic programming. How to walk on stage, shit like that.

It’s not just showing up and doing it over and over and you’ll get it?

Yeah, you could do it that way. It will probably take longer. I don’t have enough time, I started too late. [Laughs.] I’m in a hurry.

Are there advantages to starting late?

I have way more to say. You know what’s funny though is that I’ve always had a viewpoint on things. For a lot of my life I judged myself for wanting to perform. It was like (cringes), “What a lowly impulse.” Now it’s alright. The other thing about stand-up is it’s fucking interesting, and it gets you out of every social engagement you could ever possibly be expected to go to, like with girlfriends or friends. “Nah, I can’t. I got a spot tonight.” [Laughs.]

It seems like you’ve got a lot to say. I imagine that comes from being from such a large family and competing for attention.

Yeah, I’ve been a know-it-all since way back, since the 80’s. Always have been. You know where else that comes from? When I was 6, I was arguing with 20-year-olds, and I’m not talking about regular 20-year-olds, I’m talking about angry, Irish Catholic 20-year-olds who weren’t afraid of calling a 6-year-old a faggot and a moron. I’m the youngest of 10. And again, pitiless. That has a lot to do with it. One of the clearest illustrations of my know-it-all-ness was one time me, Chappelle, and Paul Mooney were at Eddie Murphy’s house, and we were talking about white people in general, and Eddie’s doing, “What is it about white people?” You know? And Eddie Murphy is my hero. In all caps. Chris Rock once said he was one of the most talented people that ever lived, and I completely agree. So Eddie’s talking about white people and I go, “Eddie, here’s the thing about white people, we’re experts on everything.” And I’m literally cutting off my hero to illustrate that white people are experts on everything, including white people. I was like “Sit down. Eddie Murphy, sit down. What do you know?”

So how did The Champs come together?

Everybody was doing podcasts, and I did Joe Rogan’s podcast, and a lot of people would come see my based on that. And Rogan said nothing was better for his career, for his live shows, than doing the podcast. He does theaters now. So I thought I should start one and was thinking about who would I want to do it with and I thought Moshe’s funny and I saw Doug and I thought Doug was funny. And then we were thinking what the angle should be, and me and Moshe both sort of have black leanings so we were like “Let’s just have black dudes on the show.” And I’ve also never had a boring conversation with a black dude. Or the odds are way higher that you’ll have a great conversation with a black dude. There’s just more shit to talk about. And then my pedigree makes black dudes trust me more. They’ll say shit that they might not say other places. If they feel like the wrong white people are watching or asking, they won’t air as much dirty laundry. I also think it’s fun for white people to listen to black people and white people talk without strain. There’s something magical about it. It’s like, “Oh look at these people who are comfortable with each other.” They’re not mismatched cops, and there’s nothing politically correct about it. Trevor Noah said Jewish people have hair like poodles. Just shit where you’re like, “What the fuck are you talking about?” You know, white people smell like wet dogs, just shit that you don’t hear anywhere else. If you like racially tinged humor, it’s like Shangri-La.

[Laughs.] Although, is there a more fucked up episode than the one you did with Felipe Esparza?

No, Felipe takes the cake. I mean, he bit a dude’s ear off. And not a very downloaded episode. If you just want to hear crazy fucking stories…[Laughs.] He goes you know when there’s an overpass, that’s a neighborhood you can buy drugs in. That was great. It’s also fun seeing Doug, who doesn’t know black people as much, be the voice of the common white person. What’s great is a lot of black people listen to it, too. Cause there’s no black people in podcasts.

Is it going pretty well? Do you follow the numbers?

Yeah, I follow them closely. We get about 100,000 downloads a month.

And the podcast has been helping you sell tickets?

Yeah. Like I did a show (a couple weeks ago) in Phoenix and 250 people came out. It was fair. It was great. That’s the thing with comedy now, you gotta give some shit away. It’s like the mixtape model, which I actually just made. Lil Wayne made three free records, and then when his record Tha Carter came out, it sold like a million copies in a week. Cause it was like, “Oh, this guy’s been giving me enough free shit, I’ll buy one.” But anyway, I did a half-hour special for Comedy Central, and since I have to basically throw the jokes away, I had an idea to take those 25 minutes I did for Comedy Central and make a mixtape with Samantha Ronson. It’s a classic hip-hop song, into one of my jokes, and then that goes on and on. That way people can have it on their iPod forever. And I made a Radiohead one, too.

Are you putting this on your website? Is it coming out soon?

Yeah, I’m gonna put it online, like everywhere. It will probably be out within the next week.

Are you still interested in making movies? Obviously everyone wants to make something that will make them a lot of money and be seen by a lot of people, but are you soured by the system? Can you get back in?

Yeah, I’ll always have the opportunity to do TV stuff. Like I’m going to direct an episode of The New Girl, and I’m going to direct some episodic stuff, which is fun cause you get to go in for two, three weeks.

What’s the last thing you directed?

I directed stuff for the ESPYs, cause I write with Seth Meyers. I directed that Dirk Nowitzki Basketball Camp sketch.

That was hilarious.

That’s one of those things where you have to be “in.” So now I’m “in” so hopefully I’ll get more. Because the great thing about directing TV is it’s like you’re just on the jury. I’m just there to help someone with a show, but I don’t have to stay there for 10 years and let people see the worst parts of my personality.

Did you direct on Chappelle’s Show?

Yeah. I got nominated for an Emmy.

Did you learn on the fly?

I went to film school at NYU, and then I dropped out to work at the comedy clubs. I was always interested, and then we did Half-Baked and I was very involved in the editing of Half-Baked. I also got a movie script that I’m supposed to direct as well – a romantic comedy. So yeah, I’m not soured per se. With movies, you kind of get one chance, and I had my chance in terms of a big studio comedy. You’re on a list, and then you just move down the list. So if a script comes to me, everybody’s passed. [Laughs.]

Where you do want to go with stand-up? Do you have an end goal in mind?

I would like to do theaters. That’s my goal. I said this to [Parks and Rec creator] Mike Schur, who’s an old friend of mine, when he asked why I was performing so much. I said “Cause I’d rather make Bring the Pain than The Hangover.”

Why is that?

It’s more personally satisfying. Bring the Pain means more to me than The Hangover does. Raw and Delirious mean more to me than 48 Hours and Trading Places and The Nutty Professor. The other thing with movies is, if George Carlin’s act was a movie, it would be a dystopian post-apocalyptic thriller. There’s something about movies that’s so cooperative and so fake. There’s something about movies where they’re upholding Judeo-Christian values that I just think is corny. I like movies, but with stand-up you can really affect people’s thought process. You’re not just an entertainer, you’re a writer, you’re a philosopher, you’re a pastor, you’re so many things. Dave’s act, Chris Rock’s act, Billy Burr’s act, Stanhope, Attell, shit is dark, man. But it’s a real reflection of the world that you just don’t get anywhere else. So that’s what I like about stand-up. If someone said to me you could be a really successful comedian or you could be a really successful TV and filmmaker, I’d pick stand-up every time…I just think stand-up’s the coolest thing ever. That’s the bottom line. I love Chappelle’s Show, but I think what I love most about it is how much it’s like stand-up. Stand-up’s just really interesting. So hopefully I’ll be in theaters based on this mixtape.

Phil Davidson worked in East St. Louis for almost two years. Now that’s some real gangster shit.

Talking to Neal Brennan About ‘Chappelle’s Show’, […]