Neal Brennan is a white comedian who often works with comedians of color. It’s a fact that shouldn’t be noteworthy, but since such working relationships continue to be a rarity, it is. Brennan found that lane by trying to work with the funniest comics he knew — and while some people might assume that such a career would be filled with awkwardness — when Brennan discusses using the N-word in a joke, for example — he says there has been none.
He’s so comfortable talking about such subjects, in fact, that when invited to discuss his work on Vulture’s new comedy podcast Good One: A Podcast About Jokes, he picked a joke he wrote with Dave Chappelle for Half Baked that has the N-word in it. The conversation that followed focused on how he navigated using the word when working with Chappelle or Chris Rock; we also got into what it was like going from writing with Chappelle to writing material for his solo career.
I’m here with Neal Brennan, the man behind that joke.
Let me preface this whole thing by saying, I wrote Half Baked with Dave Chappelle. He and I have an agreement not to divide jokes up from a long time ago. So he may have written that. I just was like, I like that joke. He may have written it. It’s not important. The important thing is that I like that joke. It’ll be like Rashomon with jokes sometimes, where I’ll be like, “You wrote that,” and he’ll be like, “No, you wrote that.”
You’ve had a long, very good career and you’ve said you don’t like Half Baked, so what made you think of that joke?
There are parts of Half Baked where you go, “Oh, the people who wrote this wrote Chappelle’s Show,” and then there are parts that you are not. The people who wrote that joke, wrote Chappelle’s Show.
In what way?
It’s a dumb entrance joke. It’s literally just a misunderstanding, sitcom joke, but a black woman calls a white guy the N-word.
Did you ever feel weird having jokes that you wrote have the N-word in it?
I don’t. I mean, there are people that do, about me. Like in my Comedy Central special that was from a few years ago, I say it and I talk about it and there are lots of people who take umbrage. It’s all the arguments: intent, it’s like a term of endearment, I’m being called it all the time, you pick up the culture you’re around. But I’m not running around advocating white people say it.
In your first special, Women and Black Dudes, you say that your friends had a meeting about when you can use it. Even before that, I imagine when you’re giving people jokes it might’ve included it.
It made me think of how I believe Mel Brooks said he partly wanted to get Richard Pryor to help write Blazing Saddles, so they could use the N-word. Or like when Quentin Tarantino writes himself to play a character that says the N-word? What was your relation to it as a word to put in jokes at that point?
I wrote that when I was 23, so pretty early on we’re talking about. Another joke that I’m partially responsible for is the joke in Chappelle’s Show where Clayton Bigsby calls white kids the N-word and then they’re excited about it. It’s never as simple as like, “You can, you can’t, end of discussion.” It’s like, “What if I’m hypothetically writing for Dave Chappelle,” or whomever I’m writing for.
And Dave never cared?
No. We’ve never talked about it. Literally never talked about it. I’m an adult. He’s like, “You know, if you get your ass whooped …” I’ve never talked to Chris [Rock] about it. I’m not saying it other than, “Hey, you should say da da da.”
Interestingly though, in Top Five, there’s that scene with DMX. I was there that day. I was there for like a week working with Chris. I was pitching that DMX say it in a line. I didn’t say it to DMX, just because I don’t know him like that. So, I said to Chris, “Sort of maybe he should say da da da.”
You don’t say it in Three Mics.
People get too upset. And I get it. I don’t want the special to be about that. In terms of saying it onstage, I’ve said my piece.
To a bigger point, it’s something that I’ve talked to [SNL co-head writer, former Chappelle’s Show and Chris Rock Show writer] Brian Tucker about. What do you think it is that makes you able to write comedy about black people, about black issues, and specifically be able to write for black comedic voices?
This is an aside, but Tucker and I went to the Knicks game the other day and we were sitting next to the rapper Jadakiss. I invited Michael Che to go, but he couldn’t go. Then we were on the Knicks Instagram — Me, Tucker, and Jadakiss — and Che looked at it and goes, “Three historic black men.”
Trevor Noah pointed this out about me. It’s like, “Dummies, why would you not try to write for black people in comedy? Like why would you not make a concerted effort?”’ I say, “It’s like not working with gay people in fashion. Dude, they’re the best. Why would you not?”
Then, I can speak for myself, it’s just an empathy level. I don’t know, I just like the whole vibe with black people. And black people just like will seek me out at this point. The irony is, as a result of writing for black people, white people see me as other. Honestly, there’s this thing of like, “Can he write for white people?”
That’s crazy. You also have worked with very white people …
Tons of white people.
Seth Meyers …
Seth is quite white. Amy [Schumer], I’ve worked with.
I’ve worked with some of the whitest. Yeah, Schur went to Harvard. Schur got a perfect score on his SATs. What could be whiter than that?
I want to get back to how this joke was written insomuch as how you and Dave worked together? You once joked that people just assumed you wrote the structure of Half Baked and then Dave would come in and make it funny. But on a practical level, how did you actually write the movie?
He pitched a weed movie without telling me, and then we had to work backward from there. There was a book called The Writer’s Journey by Christopher Vogler, based on Joseph Campbell’s classic mythic structure. I was like, “Dude, read this.” He read it, and when you read it, it’s really simple. It’s very clear. Then we had the pitch on Monday and we were screwing around for a month before, so Sunday — all day — I brought in index cards and we laid it out. I remember when he saw the index cards something in him was like, “Oh!”
We laid out the structure together and then when we wrote that, we would sit in a room, I’d type, turn the computer to him, he’d type, turn the computer … You basically try to make the other person laugh and/or improve on what they wrote. That was similar on Chappelle’s Show. I had an index card that I would write premises down on or he would go, “Hey, put that on the card.” When we had a block where we would have to write like ten sketches, we’d just take the card out and go like, “Alright, let’s write that, that, that, that.”
Are you talking it out?
We are, for sure. It’s not like dead silence. Like, “Ssshh, no, no, no, on the page.” We would definitely pitch jokes and the specific writing of it.
Were you constantly rewriting? Especially when you started directing on Chappelle’s Show?
We would never really rewrite. We would do a read-through and then we’d get on set and just go. That was the challenge of doing SNL with Dave. The Walking Dead sketch we did the Chappelle’s Show way. Me, him, and Tucker wrote it. We got on set and improvised. On Chappelle’s Show, we’d just go like, “Yeah, say this,” “Say this,” “Say this.” You can see it on the DVD — us pitching jokes.
I’ve heard that you guys would screen things a few times and then re-edit it?
Yeah, we would go to Carolines. It was like a trick. The audience would actually get mad before the show was popular. Dave would go, “I’m doing stand-up at Carolines.” Sell tickets and then do ten minutes and be like, “You guys want to watch some videos?” You could get a sense of how they would play there, and then we’d shave them down.
When Dave hosted SNL, you wrote both the Walking Dead sketch and the Election Night one. On a practical level, they’re different-feeling sketches. Compared to your past experiences, how different is it writing an SNL-style sketch?
When we first started Chappelle’s Show, people thought the blind white supremacist was too long. They were like, “You know, we don’t want to be like SNL, where the sketches are too long.” The difference between these sketches and those sketches is when you’re shooting a pretaped short film, you can go from location to location. The thing with the SNL Election Night is it’s in a room. We did do time-elapse — where we would just cut to an exterior, change the time, cut back — but it’s just dialogue. If you want somebody else in the sketch, Ding dong! I’m a huge fan of Saturday Night Live, so I always wondered, Could I write a multi-cam sketch?
Did you go through the same pitch like a regular writer on the show does?
I didn’t. I was there for the pitch, but I stood outside and let them all pitch.
Two got on the air. I heard you wrote a Rick James thing. Did you try anything else at the table read?
No, Rick James was at table. Election Night was at table. Walking Dead, we didn’t table it. The cool thing was I was in the sketch pick. Lorne really trusted me that week; he kind of let me pick a sketch on the air. As a fan of the show, it was great. Life can be really amazing sometimes in that way. When I was like 8 or something, when Eddie Murphy was on Saturday Night Live, I would watch it. I would stay up and watch it, and then my parents would pull into the driveway, and I’d hear them, and I would have to run up like two flights of stairs and hide in bed. Finally, I said to my mom, “Hey, can you let me watch Saturday Night Live? It’s important.”
And both sketches were hits.
Yeah, that was great, too. Election Night wasn’t even that good. Chris fucked a line up and Dave screwed a line up. It certainly wasn’t flawless, but it was a good idea.
That’s part of doing an SNL sketch — it isn’t perfect, but still hits.
Yeah, that’s the fun of it. The fun live part.
As an audience you’re thinking, Oh yeah, they must’ve only read that line maybe once before or They must’ve changed it between dress rehearsal and the show.
For sure. Chris added a couple jokes. That’s the thing, I was like, “Dude, you can’t screw up your own joke. You can’t force us to write this joke and then you screw it up.”
To jump back to Half Baked — Dave had the initial pitch for the movie. At that point, did you feel like your job was partly in service of Dave?
That’s always my first priority. Whoever is saying the joke is my biggest priority. It’s like Seth said, from writing on Saturday Night Live, “If a host doesn’t want to do it, don’t. You can’t force ’em.” I know from doing stand-up, I don’t want to do a joke that I don’t trust. So, I’m grateful. I texted Dave two days ago because I’m getting a lot of praise for 3 Mics: “Thank you for believing in me literally 25 years ago.” He was like, “You were always funny!” “ALWAYS” was in all caps because I wrote “LITERALLY 25 YEARS AGO” in all caps. I wanted the show to be good. I wanted him to do well. They’re tandem worries.
Like in the Walking Dead sketch thing, the ending was Tyrone gets his head knocked off, and I was like, “I don’t know.” I kept saying, “I don’t think that’s good. We need a coda.” It was a little tense between us. I was like, “Dude, I’m telling you. That’s not a good enough ending.” He had a line and I was like, “We could do a whole speech based around that.” It was a little tense between us, so I told Tucker to write it. I was like, “Tucker has a great ending.” So, it all worked out. It’s not even that funny an ending. It’s just rounder.
It’s been over ten years since you first started working on Chappelle’s Show together. Was that conflict the same conflict?
Yeah, a lot of sketches came from arguments. In some ways, it’s like I’ll put the straitjacket on him, and then he’ll be like, “Blah!” [try to get out]. I’ll be like the counterargument. The best example, and this is our favorite sketch now, is this sketch we did on Chappelle’s Show, which was Jury Selection — where he’s on all these juries. There was a Vanity Fair Michael Jackson article in like ’04. I was like, “Well, here you go! Fucking case closed. It’s all here.” Then we argued. Shadow of a doubt for black people is so huge that you can’t convict anyone. I was like, “Alright, we’ve gotta do this.” Then it became that sketch, and it was awesome.
What was it like then afterward to write for your own voice fully?It wasn’t so much figuring out my voice comedically, because that was always pretty clear. It was more about performing and being a good, watchable performer. I took a voice class — just completely started from scratch. I’m not one of these like “I just go up there and I’m magnetic.” Like Dave or Chris, though even Chris has to be very premeditated. But Dave, you watch that SNL monologue … Rock and I are watching it and Rock the whole time is going, “Don’t look down. Don’t look down. Stop looking down.” Chris is worried about looking down. If Chris looks down, it’s death. If Dave looks down, it’s not. Dave’s whole thing is like public melancholy — or that’s a big part of it.
I’ve seen Dave talk for an hour and a half, smoking a cigarette on top of the piano at the Comedy Cellar. And you think, Oh, he’s just kind of working through a thing.
Even if he’s not, that’s his gift. Dave’s gift is that last two minutes from the SNL monologue. I don’t even agree with what he said. It was leading to giving a Trump a chance. But it was beautifully said. With me, it was more a matter of, What am I good at? Part of the origin of 3 Mics is like there are people that watch me who think I come across as a smug dickhead. I was like, How can I mitigate that? And it’s like, “Here’s what I’m actually like, if you want to know. The rest of it is basically a smokescreen.” Now people are like, “Ohhh, now I like you,” from what I can tell on Twitter. Someone wrote, “Now I just want to see you win.” I’m like “great” because you wanted Kevin Hart to win just automatically. Dave you want to see win just when you see him walk onstage. But me, you need a backstory. It’s a bit of an origin-story thing. Here’s who I am. Here’s where I came from. Here’s how I came to this place of performing. My dad didn’t love me [laughs].
Do you think it’ll now be easier? It’s why origin stories exist.
Yeah, people will see me in that context. I would assume that’s what it’ll be. Now my worry is that I’m going to do shows and people are gonna go like, “I saw Neal, wasn’t that sad. Hopefully it’ll be easier, but now I’m all out of sad stories. I don’t know what I’m going to do on the next one.”
This interview has been edited and condensed.
This story has been updated with the correct spelling of Seth Meyers’s last name.