Neal Brennan has always felt like an “outlier” in the comedy world. He’s a successful stand-up who’s still best known for co-creating Chappelle’s Show and, as he jokes in his new Netflix special Blocks, he’s often the least famous comedian in a room full of some of the biggest comedy stars on the planet.
In this episode of The Last Laugh podcast, taped before Dave Chappelle’s most recent SNL monologue, Brennan talks about trying to get to the bottom of what’s “wrong” with him on stage, why he still thinks the “old Kanye” is still in there somewhere, and what he’s learned from helping other comics achieve some of their greatest work. He also goes deep on the origins of his creative partnership with Chappelle and shares his thoughts on the controversies that have consumed his friend in recent years.
There’s a joke from the special that Brennan ended up cutting where he imagines the audience making plans to go see him by saying, “Hey, you want to go see this comedian? He’s a writer.”
He found a kindred spirit in the similarly hard-to-classify “magician” Derek DelGaudio, who directed Blocks. When Brennan went to see DelGaudio’s acclaimed one-person show In & Of Itself, he picked the card that said “Comedian” in the lobby before it started. When DelGaudio pulled off his most impressive trick of accurately identifying each audience member by the card they chose at the end of the show, he got to Brennan and said, “A very good comedian.”
They’ve been friends ever since.
At various intervals throughout his new special, Brennan repeats the refrain, “Something is wrong with me.” It starts as the throwaway aside but by the end becomes an emotional revelation about, as he puts it to me, “what alienation does to you.”
“By the time they’re my age, most people are married, they have kids, most people drink, most people smoke weed, most people eat meat, most people fit into categories more comfortably than I do,” he explains. “And it just starts to eat away at you because you go, ‘What is wrong with me that I don’t do anything normally?’”
Below is an edited excerpt from our conversation. You can listen to the whole thing by subscribing to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.
You have this incredible story in your special about this party at [Netflix CEO] Ted Sarandos’ house, and it’s basically every massive comedian in one room. Do you really feel like you don’t fit in with that crew, with those people?
I will say that I am the lowest status person of that high-status group. Or, in terms of the invite list, there’s a lot of places between me and Ellen [DeGeneres] and Eddie [Murphy]. But I could argue the opposite, which is, I still got invited. And somebody has to be the least successful person there. I definitely am aware of the differences between me and the people at the party. But at the same time, I could argue that I’ve written for a lot of them, so I must be fairly good.
Yeah, you’ve done a lot of this behind-the-scenes work, whether it’s directing or producing other comics’ specials or writing for them, including people like Chris Rock, Ellen DeGeneres, Seth Meyers, Michelle Wolf. And obviously you’re the co-creator of Chappelle’s Show. You were saying before that you feel like the press doesn’t know where to put you or people don’t know how to think about you. Has a lot of it been trying to break out of that behind-the-scenes thing and put yourself out there in a way that you weren’t at the beginning of your career?
I was a writer/director, and then I became a comedian, so I understand the difficulty. Louis [C.K.] and Tina [Fey] and Larry David were similar. Then they made TV shows that were explosive and it sort of left all that in the dust. I haven’t done [my own] TV show. So I haven’t been able to clear people’s memory of the other stuff I’ve done.
Is that something that you’ve tried to do or want to do?
I’ve done pilots that didn’t get picked up. Having a TV show is incredibly taxing. So there are times where it’s like, I want to have a TV show, but I don’t want to work quite that hard. So I understand that it is hard to place me. But also, it’s hard to be compared to Dave [Chappelle], for anyone. And I don’t ever see us as comparable. I guess we’re similar writing-wise. But I think I get compared to him in a way that people don’t compare Larry to Jerry Seinfeld. So again, I’m not complaining. It’s just one of those things where I think hopefully at a certain point—Maybe now? Maybe in a week or two?—people will go, “Oh, this dude is a good comedian.”
You’ve joked in the past about how Dave’s decision to walk away from Chappelle’s Show maybe wasn’t the best for you. How did you feel about it then versus so many years later?
I’ve never liked it! Didn’t like it then, don’t like it now. [laughs] Yeah, I mean, I didn’t like it then and my mind hasn’t really changed.
Just because of all the money left on the table?
Nah, it was more, I liked doing it. And again, I’m really happy with what my life has become. But it was just a painful time. The whole middle of 2004 to the middle of 2005 is just—I don’t think it’ll ever be worse for me.
What made it so bad?
You know, from negotiating money, in a triangle of me and Dave and Comedy Central, to just after a negotiation, having to work in a challenging environment, we’ll say. It was just a very hard time to work.
I remember when he finally decided to talk about why he walked away, there was the concern about people laughing for the wrong reasons. And in your special, you have a bit about how one of your jokes, if told in a different context, could kill at a Klan rally. And you bring up the idea that intentions don’t necessarily matter in comedy. So was that something that you could relate to him about, or a concern that you shared?
For sure, absolutely. Yeah, of course. After the first season, so two years before he walked, we were in Phoenix or something. And a guy came up to us at a club, sort of a dusty white dude, and was like, “I like that sketch where the guy leaves his wife because she’s a [blank] lover.” But he said it. And it was just like, ahhh, fuck. And it’s funny, when you do racial jokes, I think it’s pretty clear whose side I’m on, morally. I believe in racial justice. I teach CRT to my dog—I’m kidding. But you can’t control what people hear. Chris Rock says that the N-word is like nitroglycerin, but any kind of racial joke is nitroglycerin. If you don’t know what you’re doing, you’re gonna burn yourself. You’re gonna burn the people around you, it’s gonna be highly damaging. So I would argue that I know what I’m doing, but even I burn myself and burn other people. So “loaded” doesn’t even get at it.
The whole idea that your intentions as a comedian don’t necessarily matter compared to how people receive your material could obviously be applied to everything that Chappelle has been dealing with in the past couple of years as well. And you reference it in your special. When you start talking about trans issues, you imagine someone in the audience warning, “Don’t go out like your boy.” So I’m wondering what it’s been like for you to watch him turn into sort of a comedy villain to a lot of people around this issue.
Look, my take on all that stuff is just, the size that Dave has grown into as a figure in American life is so funny to me I can’t even… it’s so absurd. From Chappelle’s Show to now, it’s all so crazy. I call him my cellmate. It’s like a guy I was locked in a room with for years and then he just becomes this towering figure—and deservedly so, by the way, in terms of intelligence and talent. You just don’t think it would ever get that big, because that’s absurd. I feel like I was friends with New Amsterdam and now he’s Manhattan. When I spent the lion’s share of my time with him—and I still text and see him and all that stuff, but he’s got kids and whatever—but the size to which he’s grown as a cultural icon is just funny. I can’t explain it. I have these tiny life memories with him, and then anytime I pick up my phone it’s like, “Did you hear what Dave did?”
In your special, you do some jokes about trans stuff, but I think you do it in a way that really does not make that community the punchline. And that’s one of the criticisms that’s been leveled against Dave. Do you feel like that criticism has been fair or totally unjustified? Or how do you think about all of the incoming that he’s received over this stuff?
It looks stressful. When I look at what it’s like dealing with all this stuff, that’s a level of stress that I have no interest in, that I truly don’t even think I could handle. And that’s what that joke is: “Don’t go out like your boy.” I’m not saying, don’t say what he said. I’m saying it like, don’t get involved.
What’s been a little baffling to me is him continuing to go back to the well of that particular issue. It seems like it’s become kind of an obsession in a way that just keeps bringing him more and more hate.
Yeah, I guess it’s very important to him in a way that I don’t quite understand.
It must also make you think about the fame thing we were talking about—
I should cherish being the least famous person in the room?
Is there an upside?
Yeah! There’s a huge upside. I’ve done 10 things you could really get me in trouble for.
But nobody cares?
Kind of! I always think about what will happen if I get a big boost.
It’s like what happened with Trevor Noah or someone like Shane Gillis or these people who get the big jobs and then everything looks through their stuff. Kevin Hart.
With me, it wouldn’t be worth the hits quotient. At this point, you could write a piece about me, and people would go, look at Dave! Because that's where the hits are. So there’s a part of me that is very cognizant of that.
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