Dave Chappelle

I just always loved stand-up. It's like magic. You say something, and a whole room full of people laughs together. Say something else, they laugh again. The fact that people come to see that and participate in that... I don't know, it's just like magic.

Alright. Here would be my advice. Ok, I don't know how comedians start nowadays , right? But what I would suggest is just start. And once you start, you can't really stop, no matter what happens. No matter how bad it gets, no matter what people say. you know what I mean? Because comedy is weird like that. You know why I hate watching other comedians do comedy? Not because I hate other comedians, but because I love comedy so much. Its like watching somebody else fuck your girl. And I say 'I fuck her better than that'.

I was trying to explain to my kids the other day how different my 40 was to my dad’s 40. I skateboard sometimes, play video games, buy motorcycles. I ride bikes now. Like, man, I’m a real action-packed 40-year-old dad, like, relative to what a 40-year-old was like when we were growing up. Also, I have this thing where I meet people whose kids are, like, superhuman perfect: "She speaks three languages now, blah blah." That used to make me feel shitty. Like, "Aw man, I really have to crack the whip and do this and that." But then I watch their kid for a while and then watch mine. And my kids look actually happy. And I learned early on that perfectionism and parenthood is a toxic combination fo...[Read more]

I didn’t start coming into my own as a guy until I was 12 years old. I can actually remember the moment. I went to a party. I was scared to go to this party, but I ended up going anyway. And when I got there, it was like I could tell everyone was really happy I came. And then a kid explained to me, "Man, it’s not as much fun when you’re not here." And I was like, Oh, I didn’t know that. I didn’t realize that kids thought I was funny—that I had actual friends. Even at 14, when I started doing stand-up, I was always a pack animal. I’d like to be a lone wolf, but I’m just not.

We’ve always had a strange friendship, but I don’t think it was ever as icy as people thought it was publicly. We just almost never talked about it. Like, "Let’s just not. We’re just not gonna agree on certain shit, so let’s just not." It was a valuable friendship above and beyond whatever work we did together. He’s an important part of my life. So I don’t think that will ever really change.

[not remembering his own success] is good, because what that’s allowed me to do is have a vantage point about my own life that’s accessible to people still. I could see a guy walking down the street and be like, Even though I’m famous, I got more in common with this guy than, like, Brad Pitt. You know what I mean? Like, as a comedian, there’s a certain closeness you need with people. I listen to some of Richard Pryor’s shows as an adult, and it’s more remarkable—moments when he’s talking about freebasing and Jim Brown, staging interventions, and just these kinds of bits. Or the one where he says, "He took me in the basement and showed me the monster." I mean, I get chills thinking about that...[Read more]

Sometimes there’s something I really want to convey, and I get a little obsessive about it. So there’s that. It’s not that they’re not listening, but it’s like I’m trying to say this thing to them and they can’t hear me. Like, there were times when I was famous for things that became cumbersome. Half Baked was like that, where I had grown personally, and when I would go onstage, people would scream out shit from that movie. Or like, "I’m Rick James, bitch!" And I’d just be like, "Listen to what I’m saying, listen to what I’m saying." It was frustrating—like I was being victimized by my work. I think it’s a Miles Davis quote where he says you spend the early part of your career trying to chas...[Read more]

I have said some very witty, razor-sharp shit in conversations or even, like, offhandedly onstage. Some of ’em I don’t even want to repeat. They were funny, but I just know that sometimes the things that scare you the most or make you want to cry the most or are the most tragic are the things you just gravitate to or address in a comedic context, partially because you shouldn’t. That shit’s dangerous. You know, you fuck up a lot doing that. But it’s exciting when it works, and it’s exciting to kind of just watch someone try. The short answer is, yeah, I’ve laughed at shit that I feel guilty about or made jokes about things that I felt guilty or ethically uneasy about after the fact.