IMO Podcast: w/ Dave Chappelle on Fame, Family & Finding Balance (Transcript)

And what I saw on the campaign trail was— is very reminiscent of what I felt here driving around your community. And it is just a decency and an openness and a willingness to connect with people and, as Luke said, to accept people for who they are.

And I always want to translate that to people across the country, because in a time when we don’t feel like we see each other, you know, I just want to remind people that communities like this one is really the truth of what I saw in America. It was the America I was representing, and I felt that, you know, I mean, it was oozing in every stop that we made. And I think it’s important for our listeners to understand that America has not disappeared. It is here alive and well and thriving throughout this country.

So it’s just been a thrill for me to be back on soil like this. But you were raised here. This was your community. Oh, absolutely. Or you’ve had your connection to Yellow Springs. Can you talk to us about why this community is so important to you?

Growing Up Between Two Worlds

DAVE CHAPPELLE: I think my presence, my family’s presence in this community is an extension of my father’s life work. He lived here all of my life, and a lot of the ethics of community, you know, I learned from him. My mother and he are both from Washington, D.C., so I would mostly live with my mother. But Christmastime and summertime, I would come out to Yellow Springs, and it was so much different in D.C. And it also kind of prepared me for what my life would be like, ’cause I was a kid with two lives. I had friends from out here, and I had friends in D.C., and you know, D.C. is like, you know, it’s Black.

MICHELLE OBAMA: Very.

DAVE CHAPPELLE: Right, but this town is white, and I would come out here and play D.C. records for them, and they’d be like, “What is this music?” And then I’d go home and play rock and roll stuff in D.C., and they’re like, “What is this music?” I felt like before there was an internet, I got a good sampling of culture that way.

And that upbringing really did kind of help me become the type of comedian I am. It made me less afraid of people. And this is going to sound weird here, but it made me not afraid of white people. So, in comedy, in say, the ’80s, really the ’90s, comedy circuits was segregated. Yeah, and people don’t know that, but Black comedians played one set of rooms and white comedians played one set of rooms. And Washington, which was a majority Black city, didn’t have any Black clubs until a few years into my career. Not to say that it was always like that, yeah, but for just full-time comedy rooms, you know, I started out in what they would call white rooms.

I can remember one of the owners saying when I started out that he didn’t like more than one Black comic on the show because he said it would offend his audience. It’s like, dude, it’s Washington, right? Right. But I always played anywhere that anyone would listen. And I didn’t realize I was a little older when I would see some comedians hit like an invisible wall. Like, they would never play Sunset Boulevard, or they’d never go play Greenwich Village, or certain, you know, comedy staples that they just considered white rooms. They felt safer on Crenshaw or on this place or that place. They thought they wouldn’t be understood.

And I thought that the challenge of art was no matter where you go, you should try to be understood. And that, I don’t know, something about that upbringing, the duality between Ohio and Washington, I think made me game to become what I became.

Memories of Family and Childhood

MICHELLE OBAMA: What are some of your fondest memories? When you think of the time with your father, your friendships here, how old were you when— what was your age range when you were spending time here? It was summers, it was holidays.

DAVE CHAPPELLE: My parents split up when I was 2. I don’t think they actually got divorced till I was 5, but they split up when I was 2.

MICHELLE OBAMA: What did your mom refer to your dad as? The gentleman?

CRAIG ROBINSON: The gentleman that I was married to.

DAVE CHAPPELLE: The gentleman I was married to. We went to my mom’s house today and she said, “Yes, my ex-husband used to live around here.” Dad!

MICHELLE OBAMA: She’s like, she said—

CRAIG ROBINSON: She didn’t even say ex-husband. She said “the gentleman I was married to.”

DAVE CHAPPELLE: The gentleman I was married to.

CRAIG ROBINSON: That’s it.

MICHELLE OBAMA: It’s like, oh, okay. He sounds like your dad.

DAVE CHAPPELLE: Yeah.

CRAIG ROBINSON: We can see where he gets those chops from, huh?

DAVE CHAPPELLE: But you know what’s funny? Okay, I don’t have any memories of them married. I have a couple memories of them being married, but I have a lot of memories when they were together. And it was always very polite. They never spoke ill of each other. They always found something good to say, you know. And knowing both of you, I hope you don’t mind I say this, Mom, I can see exactly why they fell in love. And I can see why it wouldn’t work.

MICHELLE OBAMA: Exactly like, time, time, let’s call this.

DAVE CHAPPELLE: You know what I mean? And I think one of the funnest or most interesting parts about becoming an adult is learning what the adults in your life were actually like. You know what I mean? And getting past the role of them being a senior, just people that came before you that were trying to figure things out. So I always joke with my wife Elaine, and I’m like, you know, I don’t feel like I’m getting older, but the kids are catching up. You know what I mean?

MICHELLE OBAMA: It’s like, when’d you get so old? Yeah.

The Radical Roots of Yellow Springs

DAVE CHAPPELLE: Yeah. It’s just like— but I have incredibly fond memories of living here. Now, when I was younger, I should tell you, this place was different because Antioch College was a much stronger force in the town. And your viewers aren’t going to know Antioch College. If you think of the most radical leftist politics, go left of that. And that’s what this town was about.

There was a policy that Antioch made years ago that everyone used to make fun of called “Ask Every Step of the Way.” This was 30 years before the #MeToo movement. That was like if you were getting ready to, you know, you know.

MICHELLE OBAMA: Yeah. We know. We know.

Life in Yellow Springs

DAVE CHAPPELLE: Well, you know, and then he would be like, “Well, may I kiss you?” Or, “May I do this or that or the other?” You would ask. Right. And, man, the whole country was laughing at that policy. And even I was like— ‘Cause I’m watching. I was living in New York at the time, watching the news, like, “Oh, they’re making fun of Yellow Springs.” And so I came home for Thanksgiving, and I found out that my father’s widow wrote the policy. Wow. He was alive at the time. And I asked him, like, “Yo, John, what was that?” And she explained to me the reasons for the policy.

And I laugh about it now because it’s so much like what Hollywood just went through, all this weird ambiguity. And it’s like, how do you teach young adults how murky sexual contracts are? ‘Cause if you make ’em correctly, no one should see you make ’em. And, you know, as odd as it sounds, it worked. The problem was that people on the campus were— there was like an astronomical amount of sexual assault accusations. And she says, like, as an administrator, by the numbers, you have to recognize that can’t all of these be true, but you can’t dismiss any of them. So we have to teach them what it is, and it worked. Those same numbers plummeted.

So Yellow Springs, I say that to say, has been on the cutting edge of solving certain types of problems that Americans face all the time. This is a thinking person’s town. I love doing all kinds of stuff, but man, and this is going to sound crazy, I have the most joy thinking. I told my wife years ago, I know you remember, I said, “Babe, if you ever see me staring off into space, don’t bother me, ’cause I’m working. If you see me writing something down, I’ve already done the homework.”

MICHELLE OBAMA: I’mma try that with Barack. Don’t bother me, I’m working.

DAVE CHAPPELLE: It is like that.

MICHELLE OBAMA: I’ll just be like, you can blame Dave for that.

A Typical Day in Yellow Springs

CRAIG ROBINSON: You know, this is such a wonderful place. I’ve only been here a couple of days. I went to get coffee this morning and I must have seen 4 or 5 folks. They all said hello as if they had seen me before. Thank you for that. But what I think our listeners and viewers want to know, what’s a typical day for Dave Chappelle in Yellow Springs when you’re not thinking?

DAVE CHAPPELLE: Well, I was going to say, I get up at 4 AM and stare off into space.

MICHELLE OBAMA: Stare off into space.

DAVE CHAPPELLE: Well, okay, this question is actually at the core of why I like it here. Because the days are predictable and they’re simple. Not— I mean, look, the rest of a public person’s life, it’s like circus fodder. Not nearly what I’ve experienced with you today, ’cause I can’t even imagine having that many people have to be involved in every move you make. But public life is not an easy life.

But for me here, like, everyone’s as famous as I am here. We all kind of know each other. We all see each other every day. So, you know, I know a lot of names. I know a lot of faces. I have people here that I love. I have people here that I love not liking. Like, if something bad would’ve happened to him, I’d miss—

MICHELLE OBAMA: Not like me.

DAVE CHAPPELLE: Man, I would love to fight with this person or cold shoulder this person. But it’s that kind of culture. And, you know, I’m not that old, 50 years old, but there’s a whole generation of kids that I watched go from, like, nothing to adults, to like strong, really wise adults. It’s just, it’s irreplaceable. It really does remind you of the value of people.

And I think most people don’t— you know, I’m lucky ’cause I get to be celebrated for what I do. But I think most people forget how much they influence the people around them. And there’s people here that I’ll see and I’ll know from the rumor mill that they’re going through something terrible and I’ll see them smile through it and, “Hey Dave, good morning.” And I admire that and it reminds me to be the same.

And then when I go out in the world, I can be more courageous ’cause I know I have a place where if I completely wiped, and came back here, they’d just be like— they’d all smile. “Good morning, Dave.” Even though they knew I wiped.

MICHELLE OBAMA: And I’d be like, hey.

DAVE CHAPPELLE: And that’s just why I love it here.

The Value of Simplicity

MICHELLE OBAMA: I mean, it’s so important to kind of emphasize that point of simplicity in a time where especially young people are, you know, they’re suffocating themselves with so much stuff. And I just want listeners and folks to hear this from one of the most famous men— you know, because I know I feel that way. I know Barack feels that way, is that we are striving for fame, for notoriety, for all the wrong things. And the truth of the matter is that life is about that small stuff.

DAVE CHAPPELLE: That’s right.

MICHELLE OBAMA: You know, it’s the small connections that you make with people. It’s about relationships with your neighbors and your family members, and you can’t get that by holding a phone. And it is so important when we look at rates of depression and anxiety that our young people are feeling, it’s because they’ve moved away from the simple— you know, just the— why did you— you told us about how, you know, every morning you walk out of your house and you go over the red bridge and you walk down the bike path and, you know, you know your neighbors and you see those rolling hills and the trees and you take in the air. It’s like hearing you, Dave Chappelle, say that that is the key to your joy and your sanity is powerful.

DAVE CHAPPELLE: I mean, it means everything, you know, especially with comedians, right? So fame is one of the worst things that can happen to a comedian as an artist because you’re sequestered. You know, life is— this is not my case, but it’s not authentic, your life. You know, the yes people or whatever the clichés are. But this place, man, this place does not do that. Like, man, at times I really wish that they would. They don’t though. They just don’t. And I wouldn’t trade it.

And the other thing is that I do get to just talk to people, which a lot of people— you know, ambitious people especially— you’re going to forget how much you need to just talk to people. I used to shadow my dad around town. He had this thing he would do, not with everybody, with certain people. “Hey, how you doing?” “Hey, I’m good, man.” And they would look at him and be like, “Now how are you doing?” And then they’d say what the real thing was. But then it taught me again, everyone’s like a book that I haven’t read.

MICHELLE OBAMA: Yes.

DAVE CHAPPELLE: And man, sometimes I can get past the cover and man, I learned so much from so many unlikely people. And then of course I take those lessons around the world and make millions and millions of dollars. I’m just kidding, I’m just kidding.

Dave’s Parents: The Greatness Whisperer

MICHELLE OBAMA: You don’t know. It shouldn’t be a surprise to anybody. You know, Dave, you’re not just one of the funniest people out here, but you are one of the smartest men that is on the public stage. Way to go, Mom. So it’s no surprise that your parents are badasses.

DAVE CHAPPELLE: Oh yeah.

MICHELLE OBAMA: Especially your mom. Can you talk a bit about her, your relationship with her? As you said earlier, what did you say? She—

DAVE CHAPPELLE: She—

MICHELLE OBAMA: She was— she championed you. You had a way to—

DAVE CHAPPELLE: I said she put that battery in my back.

MICHELLE OBAMA: That battery in your back.

DAVE CHAPPELLE: My mom is— I called her a greatness whisperer.

MICHELLE OBAMA: That’s it. A greatness whisperer.

DAVE CHAPPELLE: Yeah. She would say things that I still meditate on that made me not want to be great as much as— and this is going to sound arrogant, but it’s not as arrogant as it sounds. Almost, but not quite. She made me not afraid to be great. I think so many people who have greatness inside of them are timid or don’t shine as much or don’t want to out-exceed anybody. “I don’t want to be noticed.” Because there’s a target on you that comes with that.

And my mom kind of put the soap in my back. Or if someone said, “Or else,” my mom would teach me and say, “Oh, or else what?” You know what I mean? Just ask, or just move, or just take the step if you feel— but she— but it was very moral because she also gave me lessons in what humility actually is. And she gave me antidotes for self-loathing. I feel like people just swim in a broth of just shame and self-loathing a lot.

MICHELLE OBAMA: And how does she do that?

DAVE CHAPPELLE: How does she make me not?

MICHELLE OBAMA: How did she— what was that antidote?

DAVE CHAPPELLE: Well, I mean, there’s one I mentioned when I got the Twain Prize, and I said this really moved people, but something she used to say to me all the time. She said, “Sometimes you have to be a lion so you can be the lamb that you really are.” Because she saw me being timid and she was like, it’s okay. She used to tell me not to be afraid to fight. “Let your hands go. Can’t win a fight without letting your hands go.”

CRAIG ROBINSON: Okay, Mom.

Growing Up, Finding Comedy

DAVE CHAPPELLE: Okay. Yeah, she— but for real, she taught me— this is going to sound— it’s not going to sound— I can’t explain this, but she taught me how to not be afraid of getting in trouble because she was my authority figure.

MICHELLE OBAMA: So you’re his problem. Yeah, no, I’m just kidding.

DAVE CHAPPELLE: But she was a loving authority figure. And to both my parents’ credit, they didn’t just bombard me with rules, they helped me understand the rules had reasons. And we didn’t agree.

MICHELLE OBAMA: Young people, don’t we snap for this?

DAVE CHAPPELLE: Yeah, yeah, the rules had reasons. Yeah, I know you know about that. I see an activist in the front row, that’s why I’m texting.

MICHELLE OBAMA: But that sounds so much like our parents. I mean, we were talking in the car about how blessed we were to have two parents who loved us, you know, mother and a father that poured into us. But a big thing was, I talk about this all the time, our mom loved our voices, you know?

DAVE CHAPPELLE: Yeah, nice.

MICHELLE OBAMA: I mean, she just loved our dirty draws and loved everything that came out of our mouths. And she was interested and curious. But they— our parents both were. And it’s that pouring into us, but the humility that comes with, you know, you don’t just tell a kid no, you tell a kid why and how. And we got that every step of the way.

And it’s amazing how that little simple thing of seeing a child, valuing their voice, giving them some boundaries, giving them some humility— that’s better than stuff. That’s better than iPhones and new cars and the best sneakers and contacts and connections. We didn’t have any of that.

DAVE CHAPPELLE: Right.

MICHELLE OBAMA: But we had parents who put that battery in our back.

CRAIG ROBINSON: And even if we— this is what I remember is it didn’t matter how ridiculous the things we said.

DAVE CHAPPELLE: Right.

CRAIG ROBINSON: She didn’t— What she did was she would ask questions to encourage us to get to the point we were trying to make. And that patience is what I remember and what I think gave me the confidence to be intellectual and successful that way.

DAVE CHAPPELLE: And you was South Side of Chicago intellectual.

CRAIG ROBINSON: Yeah.

MICHELLE OBAMA: Oh yeah.

DAVE CHAPPELLE: Were you ostracized for, no disrespect, but you are renowned nerds, both of you, right?

MICHELLE OBAMA: Well, you had to—

DAVE CHAPPELLE: Let’s get it.

MICHELLE OBAMA: No, you had to learn to be. You had to learn how to fake the funk. You had to talk two languages. You had to talk the language of, “I got an A, but let’s not talk about it, ’cause I gotta get home, too.” And you had to, you know, own your intelligence. Now, my brother had basketball to help him.

DAVE CHAPPELLE: So, everybody loved you, ’cause you could play—

MICHELLE OBAMA: Oh, my God, yes.

CRAIG ROBINSON: You just played every sport and— throw out the N-word every now and then.

DAVE CHAPPELLE: Yeah, it works.

CRAIG ROBINSON: You know, that always works. Show that he’s hard. Show that I’m a little hard, but don’t tell my mom I said that.

DAVE CHAPPELLE: You didn’t have to fight because you were a baller. Everyone loves a baller.

CRAIG ROBINSON: Everybody loved ballers, but I didn’t become a baller until I was about 12. So I had my share of fights before I was 12 years old.

DAVE CHAPPELLE: Right.

CRAIG ROBINSON: And unlike your mom, my mom would be like, be careful fighting because you’re bigger than everybody.

DAVE CHAPPELLE: Oh man, my mom was like, he better bite, n*a, he better fight.

CRAIG ROBINSON: See, if your mom was at my house, there would have been a couple ass whoopings going on.

The Music of Laughter and the Pull Toward Comedy

DAVE CHAPPELLE: But you know what else it was about you, Mom, that I love is, okay, my mom’s laugh is like music. And her mom’s laugh was like music, and my grandfather, her dad’s laugh was like music, man. And I think that’s another thing that made me want to be funny, just hearing that music come out of them. It made me feel joyful.

CRAIG ROBINSON: At what age did you realize that? Because one of the questions I was thinking about when we were talking about talking to you is you were smart enough and talented enough to pick a whole lot of different avenues, but you picked comedy.

DAVE CHAPPELLE: So, okay, yeah. Or I don’t know if I picked it. Okay, so I can’t remember a time when I didn’t feel like I was a funny guy.

CRAIG ROBINSON: Okay.

DAVE CHAPPELLE: Or some kind of equivalent of like, yeah, I’m just so— like, that was my thing. But I didn’t know that was a thing. When I was 8 years old, my grandmother had a friend come visit, who was a jazz singer, Johnny Hartman, the famous jazz singer, one of the only vocalists that John Coltrane has ever recorded with. Beautiful voice, smoked cigarettes, his voice sound like velvet, so smooth. And I remember I had just done a book report on Dr. Charles Drew.

MICHELLE OBAMA: How old were you?

DAVE CHAPPELLE: I was 8. And I was thinking, you know, I was going to be a doctor. And I showed the guy the book report and he goes, man, he goes, that’s good. I go, I want to be a doctor. He goes, nah. He said, ’cause I was cutting up all day. I was 8, he said, “You’re going to be a comedian.” Wow. And I go, “What’s that?” He said, “Oh, you know, like Redd Foxx or Richard Pryor. You know who that is?” I’m like, “Yeah, yeah, I watch.” You know, from Sanford and Son. I don’t know him like he knows him. He said, “It’s a person that’s funny for money.” He goes, “You’re going to be one of those.”

And I thought about that. I think about it every once in a while. ‘Cause you know, he’s long passed away, God rest his soul. But whatever he saw in me that day, he saw it so clear that it scares me to think back at it. I’m like, so like, did I choose this or did I? But when I finally did do standup, you know, to me it feels like a lifetime. It was only 6 years from 8 to— I was 14 when I started.

CRAIG ROBINSON: 14.

DAVE CHAPPELLE: Yeah. Wow. Which didn’t seem crazy at the time. Yeah, yesterday I got a text message from a comedian I started out with. He’s kind of a famous guy, Patton Oswalt. Yeah, yeah, he sent me a video that one of his fans has sent him, and I couldn’t understand. They were in some like dilapidated room, and then he pans over and I look, and it’s the stage that we had both started on.

MICHELLE OBAMA: It was in— was it in DC?

DAVE CHAPPELLE: On 14th and L Northwest. Is ironically, drum roll please, it’s a gay club now. Yeah, but it gave me chills just to see it because it all happened so fast. I can’t believe how far I came.

A Mother’s Role in Shaping a Career

MICHELLE OBAMA: There are a lot of creative kids in communities across the country the land. Being a creative, being— going to show business, I mean, for most Black parents, they’d be like, you better get you a good job. What do you— what are you talking about?

DAVE CHAPPELLE: Yes, exactly.

MICHELLE OBAMA: You know, but your mom did the exact opposite. I mean, she got you on stage. She thought about the education that you would need. Wasn’t she the one that suggested that you go to one of my favorite high schools on the planet.

DAVE CHAPPELLE: Duke Ellington.

MICHELLE OBAMA: Duke Ellington in Washington, D.C.

DAVE CHAPPELLE: Yes, she was. I think what, you know, not just that, she would sit with me, you know, after school she’d meet me. We’d go to the comedy club. We’d sit there all night. We’d eat fries.

MICHELLE OBAMA: Your mom would go to the comedy club with you?

DAVE CHAPPELLE: After she had been working or doing whatever it was she did that day. And I didn’t realize it at the time, but, you know, she’s a mom. She was auditing the scene. Now, I don’t think she necessarily thought I was going to be a famous comedian, but at that time, the crack epidemic and everything, all the bad things I could be doing, and I expressed such this earnest interest in being a comedian, and so she shepherded me.

She figured out who was trustworthy and not trustworthy, and, “Okay, could you come give my baby a ride home if I leave early?” and that kind of thing. And then by the time I was 16, I was a professional. Like, I would get gigs and make money, and I didn’t need her to go as much. And then that was kind of sad because her baby was growing up.

But the big one was not going to college because I’m the first person since slavery in our family to make that choice.

MICHELLE OBAMA: Like, everyone since slavery— Way to go, Dave. Way to break the cycle of education.

DAVE CHAPPELLE: Someone needs to break the cycle.

MICHELLE OBAMA: This cycle of learning.

DAVE CHAPPELLE: But I ended up moving to New York and honestly, maybe it was the best education that a person could ever get. But the guardrails of that education was ambitious. Ambition, not just like, really artistic ambition. I was enamored. I always looked at comedy like, what else can it do? And I still experiment with it. Which is more dangerous now, but no less rewarding. This job never gets easier. It’s never not fulfilling and it’s never not challenging.

The D.C. Comedy Scene and Early Influences

CRAIG ROBINSON: So at 16, you’re a professional on the road, on your own. Who were your influences? Who were your— did you have any mentors? Did you do it solely by yourself?

DAVE CHAPPELLE: No, no. Okay, so the local scene in D.C. was popping. Like I said, Patton, who went on to be famous, he was there. A guy named Tony Woods was one of the big guys on the scene. BET had just started, and it was local in D.C., so Chris Thomas was doing all these things on BET. Tommy Davidson was on In Living Color, but he was from our local scene. Martin Lawrence was just getting big, but he— but these were all local guys.

So I wasn’t on the road yet. I would get a road gig here or there. But the principal at Ellington used to give me excused absences if I left on Friday to go on the road, ’cause it was an artistic pursuit. And I’d catch the train up the Eastern Seaboard and get a gig here or there. But it was mostly happening in town, in Washington.

And the scene was very experimental and very competitive, but there was a lot of camaraderie on that scene. New York was different, but man, D.C. was, I think, the perfect place to start because I had enough room to get good.

The Art of Comedy: Style, Storytelling, and Finding Your Voice

MICHELLE OBAMA: Is there a point in a comedian’s development where they determine what kind of comic they want to be? I mean, you are a gifted storyteller weaving in life and observation and taking us full circle. Did you have to become that? Did you know that as a kid that that’s how you want to make people laugh?

DAVE CHAPPELLE: That’s a very good question.

MICHELLE OBAMA: Thank you.

DAVE CHAPPELLE: No, that’s like a very good question. There are certain— people ask me, who are your favorite comedians? And it’s not like that. In my mind, it’s a dunk reel of just different comedians doing different things that amaze me, some more consistently than others. But any night it could be just some guy who just says the thing of that night.

But when I was in high school, and I can’t remember who I saw do it first, the first time I saw a guy do what we call callback a joke — make reference to something they referenced before — I’m like, “Wait a minute, do the same joke twice?” And from then on, I’m telling you, I’m like those guys that can draw a perfect circle freehand. If I went on stage with no material, I would just know what to do. But I’ve been doing this so long, comedy, it’s almost like a language that I know how to speak. I can say anything in this language. But there are real parameters, and it’s like music. You also want to break out of those parameters. Like a bebop guy. Like, “I don’t want to play the same stuff everybody plays.”

But that being said, in my life, I’ve seen some of the greatest comedy ever done. And I feel so lucky to have seen all of it. But what made me want to be what I’m like is a long story. Can I tell it?

MICHELLE OBAMA: Please. This is your interview, Dave Chappelle. Please, take your time.

The Richard Pryor Moment That Changed Everything

DAVE CHAPPELLE: I have so many questions. It feels dumb talking about myself around y’all, but I’ll try. Okay. The single most impactful thing that I’ve ever seen. I was maybe 19 years old. I opened for Richard Pryor at Newark Symphony Hall. And I got there early, and I met Mr. Pryor before the show, and I could see — I was eyeballing him — that he’s not— he wasn’t feeling well. Now, by this time, everyone knew he had MS and all that. I just don’t know what MS does to people, but I knew that whatever it does, it was doing it.

And so I say to myself, “You know what? I want to do good, but let me just take it easy, ’cause it’s like a legend.” So I just did the housekeeping job. I got the crowd good and warm, and they didn’t want to see me anyway. They wanted to see him. And then I go and I get off the stage. He had the intro where his man goes, “Ladies and gentlemen, the most two beautiful words in comedy, Richard Pryor.” The crowd goes nuts. And he goes out there, and you could tell early on that this was not— this was not his night.

And maybe 30 minutes into his set, he stops, and it’s something I wouldn’t even know you could do. He looks around, he goes, “Look, I want to do this for you guys, but I’m not feeling well. I’m sorry. I don’t got it in me tonight. I’m sorry.” Just like that. And you could hear like a pin drop. And then this guy in the back of the room jumps to his feet. He jumps up, he goes, “We love you, Richard!” And the place exploded. Longest, loudest ovation. It went on and on. And he stood there.

Okay, I’m young, right? But then I realized what I’m looking at — that this is his last show for them. They probably will never see him live again. And people were crying and wiping tears out their eyes, and he looked a little emotional. And to me, it was the first time I had seen actual love, like, bouncing off the walls. Like, “Man, they love this person.”

And if I had never seen that, I wouldn’t even know that’s something to want. Because no one has it like Richard, like that. And when I saw that, more than any type of style, I’m like, “Man, I want to be like that.” And that notion made me work, I think, more patiently than I would have. But that was the moment I knew that fame was one of the things I wanted. But whatever the hell that thing Richard had, that moment— Whew!

When the Love Doesn’t Come Back

MICHELLE OBAMA: So then what does it feel like when it doesn’t work?

DAVE CHAPPELLE: Now it does. Okay, this is a good question. You mean like if I do a show and it doesn’t go well?

MICHELLE OBAMA: You know, that and when the love doesn’t come and the opposite comes.

DAVE CHAPPELLE: Oh, okay. Well, okay. Okay.

MICHELLE OBAMA: It could be both and.

DAVE CHAPPELLE: Yeah, maybe it’s more like in my experience it was both. ‘Cause I was doing jokes that some people thought were controversial and some people didn’t. But that experience, from my perspective, is much different than what it must have been like watching it.

Because, listen, people would think it’s me versus the gay community. I never looked at it like that. I always thought it was corporate interest and culture negotiating itself. So most of those people who were critical of what I was doing didn’t seem like they were of it. They had their faces pressed against the glass commenting on what we were doing in there, but they weren’t in there doing it.

And I think I spoke to you about this earlier — every opinion you can think of is represented in a comedy club. Every type of person you can imagine does stand-up comedy. Transgender stand-up, economics, Black, white, Asian, every kind of perspective, and we all champion whatever opinion we champion. We would never think to silence one another. We might duke it out on stage in the sense of like if someone says something racist and I get mad, I’ll be like, “Yo, put me up next because I’m going to say something about what he said.” But silencing that person wouldn’t be anything. And then after the show, we all be upstairs drinking, and we might still talk about it or argue about it, but that’s our life. And we’re artists, and that’s what we do. And we have this outlet.

So for a media outlet to speculate on a comedy show that they weren’t at, or misinterpret a joke — nothing makes a comedian madder than reading his joke wrong in the paper. And reading a joke is nothing like hearing it. Or being one. And the intention of a comedy show is a very unique intention. We are playing with whatever the culture is made of, and we break it down and we get it right or we get it wrong. But in all art, if it’s going to be good or even hopefully great, you gotta have a margin of error.

And what they were doing was acting like thought or speech was binary, like everything’s either this or that, but all art is in between it. It’s all nuance. So when they take nuance out of words and just like, “Did you hear what he said? He said—” it’s like, “Yeah, but that’s not what I was saying.”

Being in the Room vs. Watching Through the Glass

MICHELLE OBAMA: So we talked about — the first time I realized, “Oh my gosh, I’m in politics” — was my husband’s running for president. I was campaigning heavily for him, but my experiences campaigning were in communities like this. It started small, and then it grew from there. And all my conversations would be like this, extemporaneous, talking to a group, introducing myself, telling a joke, trying to humanize myself and my husband, introducing us as real people, but not on script.

And there’s a difference in how you would see the crowd respond right here. We’re all in the room together. Maybe the words wouldn’t be exact, but we would all be able to feel it. And that feeling wouldn’t just be a small group. It could expand into a stadium, an arena. The people there could feel the intent. But then I realized, “Oh, it’s not about the people here. It’s about the people with their faces pressed against the wall interpreting what I said without being there.”

DAVE CHAPPELLE: Or even more insidious, trying to bend what you say to make it more interesting or salacious, because they have a different— I don’t know. I don’t know why they do all the stuff they do, but I do know in recent years, you’ll hear a lot of comedians complain about that. And what they’ll say is, “We can’t say anything.” That’s not true. You can say anything that you can get away with.

MICHELLE OBAMA: Right, right.

DAVE CHAPPELLE: And that’s the skill. The negotiation with the audience of what’s acceptable is what makes the genre so interesting, and it could change from room to room, night to night. Every room’s a little different.

MICHELLE OBAMA: Oh, well, you said younger comedians are a little bit different because they’re not — their audience isn’t in their room.

DAVE CHAPPELLE: No, they’re internet people.

MICHELLE OBAMA: They’re internet people. And it goes back to the whole point of community. Sharing a space with people is really important to connection and understanding. And it’s no wonder why we feel so divided, because all of our interaction is happening without this heart-to-heart feeling, this even seeing somebody’s face nod and, “Oh, you get it,” or maybe you don’t. We’re losing that. And you said young comedians nowadays have a different ethos because a lot of them are not in the room.

DAVE CHAPPELLE: Negative too. Yeah, because that gets more engagement. If they talk bad about somebody, they’ll get more clicks and more engagement. So everything’s a diss record now, and it used to be — it’s not like that.

Chappelle’s Show: Comedy, Creativity, and Corporate Battles

CRAIG ROBINSON: Can we talk about The Chappelle Show?

DAVE CHAPPELLE: Oh yeah. Oh yeah, yeah, sure.

MICHELLE OBAMA: Yeah, really.

CRAIG ROBINSON: I just — when I think about you doing that show, I think about how much fun it must have been just sitting around with your friends and your boys thinking up ideas to be on Chappelle’s Show.

DAVE CHAPPELLE: Man, that’s the truth. I had one guy that I primarily wrote the show with, Neal Brennan, and we’re still friends. But one of the things we would do is we would take submissions. We’d always rewrite the submissions, but a guy gave us an idea, like, “Oh, that’s funny, we’ll write it up.” And if we use it, we pay him.

CRAIG ROBINSON: But it was awesome. That was the thing, I would have been submitting.

DAVE CHAPPELLE: Yeah, it was fun. But it was my first time being corporately funny, and it got me ready for the next time because there’s always a negotiation with the network. But I liked, in hindsight — because we had pitched that show to HBO, and boy, they turned it down in spectacular fashion. Because at that time they had The Chris Rock Show and they felt like they were invincible. But we went on Comedy Central and shot Lights Out. And I think the show was better on Comedy Central because it was an era of “you shouldn’t be able to say these things.” HBO looks like you just do anything anyway. But on Comedy Central, that dance around standards and practices was joyful.

And shout out to South Park, because I remember one time I did a Tyrone Biggums — a character I play on the show who had an addiction problem. There’s no nice way to say it, Craig. He takes a sh in the alley.

CRAIG ROBINSON: Yeah.

DAVE CHAPPELLE: And the Renée, the standards and practices lady, calls me upstairs and she’s like, “Look, you can’t have Tyrone take a sh in the alley.” And it was gross too, because we took like a Baby Ruth bar and melted it, and then we just dropped it in the frame. It was really gross. But really funny.

CRAIG ROBINSON: Really funny.

DAVE CHAPPELLE: She goes, “You can’t do that. You can’t do that.” And I go, “I don’t know, how about this, Renée? What if I put a Christmas hat on it and make it sing A Christmas Carol?” And then she goes, “Okay, okay.” So we got away with a lot of stuff because South Park pushed boundaries and people got away with stuff because we pushed boundaries. But it was all about just making room for everything.

And to their credit, especially at that time, television was governed the opposite of the internet. It was called least objectionable programming. “How do we make sure everybody likes everything everyone says?” And that’s obviously impossible. But they were brave in the sense that they would let us challenge a lot of conventions. Chappelle’s Show was fun. Charlie Murphy. Oh my gosh.

CRAIG ROBINSON: Yeah.

Charlie Murphy, Rick James & The Chappelle Show Legacy

DAVE CHAPPELLE: You know. Really? May he rest in peace. Yeah. You know, I used to see Charlie Murphy in Hollywood at parties. I shouldn’t say this, but one night I— man, I’m sorry, Mom. I was high on mushrooms. And I went to— —someplace.

MICHELLE OBAMA: He’s okay now though.

DAVE CHAPPELLE: Yeah, and I’m fine, I’m fine. But I say that to say, if you were on mushrooms and ran into a personality as intense as Charlie Murphy, it’s like daunting. He’s got a— he talks through his teeth. What’s going on? And he’s real gangsta and he got that growl.

But man, this one night I ran into him and the whole night just became about watching this guy, Charlie Murphy. Now, I didn’t know in the near future we would work together in such an intimate capacity, but that night, I could see something great about him.

And he would always talk about Eddie, but he always go, “My brother, my brother, this my—” And if anyone said anything bad about Eddie at any point in his life, he’d smack the s* out of them. He loved his brother so much.

But what I learned that night— ’cause he was always a villain in movies. He was hilarious. He was like an artful storyteller. All his stories had all this texture. And then one day on the set, we were doing some sketch, and Charlie is telling us all these stories about coming up with Eddie.

And in the middle of lunch, he goes, “Someone said something about Rick James.” And he said, “Man, I fought Rick James on 5 different occasions.” And we were like— What? And man, he started telling us all the times he beat— in every story he beat up Rick James and all this. And man, we were dying laughing.

And we pulled Simon, like, man, can we do that on the show? He said, wait, wait, you want me to beat up Rick James on the show? I’m like, not really. And we just had him tell the stories and we dramatized them.

Now, as we’re shooting it, it’s like— because we were on set dying laughing. And then here’s the kicker, then we’re on the set and Charlie goes, “I bet you I can get Rick to come for this.” And he did. He did. We ended up doing one sketch with Rick James and then another sketch about Prince.

Yes. And I asked Prince to do the sketch and he was like, “No.” But then when he saw it, he said he wished he had. And by all accounts, by his own account, he loved that sketch.

So that was just— it’s just one of those things where— and the other thing about that Rick James sketch, last thing about it, is Charlie made us show it to Eddie first. So I’d never been to Eddie Murphy’s house, but when we go, it was with his brother, and Eddie has this big screening room downstairs, and he’s sitting in like a big armchair with his back to us.

And no one’s seen the sketch, so there’s no laugh track on it. Chappelle Show had a real laugh track. And man, he didn’t laugh once. And the sketch was like 10 minutes long. And man, I’m sitting behind him with a pit in my stomach.

And then the sketch goes off, and he doesn’t even turn around. But from behind him, I see him raise his arms like this.

MICHELLE OBAMA: Oh, yeah.

DAVE CHAPPELLE: And then he turns around and goes, “It was a red couch and Rick had on capizios.” That’s what he said. And he gave us the green light and he let us do it. And to me, it’s one of the greatest sketches ever. It sure is.

MICHELLE OBAMA: I mean, I think I watched that once a month. At least once a month.

CRAIG ROBINSON: Well, being from Chicago, the Players Ball is lights out and so accurate.

Patrice O’Neal, Vulnerability & The Art of Acting

DAVE CHAPPELLE: You know what’s funny? When people ask me what the— to me, that was my favorite day of shooting. Really? I laughed more on that. Not necessarily my favorite sketch, but those characters are the ones I revisit the most. And it’s not as fun to do without Charlie, but it’s still fun to do.

And man, that was like Patrice O’Neal, who was a great, great comedian. He and I used to— like, hate each other? Because he’s an asshole, man. And I don’t mean to say it because he’s dead, but you know, Kevin Hart and everyone get mad when I say that because they love Patrice so much. I love him. I got there. But at that time, I was the guy to beat, and Patrice was new in town, so he would always— he was like, before the internet, he was a perfect troll.

And there’s a few people I’ve met in my life that just knew how to push my buttons. And man, Patrice could play me like a keyboard. He just knew how to make me mad. And then one day I snapped, and when I finally yelled at him about it, he was like, “Dave, Dave, think about it, man, think about it. I talk to everybody this way.” And I’m like, that’s true. And then I started laughing.

MICHELLE OBAMA: Like, get over yourself. Yeah, yeah, yeah, he was that guy.

DAVE CHAPPELLE: And then that same week, I’m like, you know, we wrote the sketch and I’m like, yo, let’s call Patrice. And he was great. And one of the things that made me love him for doing the sketch is that when he showed up, he was nervous, which was a huge honor that he cared as much as I cared. And man, we were good up until the day he died. We were good.

CRAIG ROBINSON: And are you guys, and when I say guys, men and women comedians— how do you train yourselves to be such good actors?

DAVE CHAPPELLE: Well, I don’t know that everyone can do it. I’m not going to say any names, but I think for me it was definitely Ellington. Okay. You know, there’s a vulnerability that an actor has to have that I don’t know that comedians are necessarily vulnerable the same way. And we’re at the mercy of a script— unless you’re working on something flexible, you gotta service the writer’s words. But acting is an amazing skill.

Now, this has nothing to do with me, but the fact that it’s one of my favorite performances I’ve ever seen. And I think I told you about this. I saw you once in Martha’s Vineyard. Denzel Washington in Training Day is like watching the most technical, perfectly technically perfect— it’s like everything I learned in school, he executes perfectly. If you know what you’re looking at, it’s amazing.

And in the Academy Museum in LA, they have his script with the marked-up margins, and I saw it, and it just reminded me of how much work this guy puts into acting and how serious he is. And I don’t think a lot of comedians would be that serious.

But Richard Pryor was a great actor because he was vulnerable. Katt Williams is a guy, every time I see him act, I’m like, man, he should do that more because he’s great at it. Surprisingly great at it. And he never studied a day in his life. I don’t know how he knows how to do that. I went to school. I read books and I can do it, but some people can— it’s like music. Some people can just play. I don’t know how.

MICHELLE OBAMA: Do you feel like you tap into that vulnerability?

DAVE CHAPPELLE: Well, I do. I think I’m more vulnerable on stage than most comedians. Yeah. I’ll say anything when people feel like they can’t say anything, which is a vulnerable position to put myself in. But some jokes, it’s like I just gotta— I just want to see if it works. I don’t want to not try.

And I think that I’ve, over the years, cultivated an audience that’s more forgiving than most people’s, than a casual comedy observer would be. These people, I think, almost come to experience the danger, because the audience is also vulnerable. Yeah. If you’re taking it out of bounds. Yeah. I don’t know.

Walking Away from the Show

MICHELLE OBAMA: So there’s much talk about you walking away from the show. It’s been discussed, but I find it— I was reading something where you said, you know, you just went out of the country for a week or so.

DAVE CHAPPELLE: Yes, it was gone for 2 weeks.

MICHELLE OBAMA: It’s just like, you know, what do you think it was about that time that made people lose their minds over you making a decision that was preserving yourself?

DAVE CHAPPELLE: I think at that time, it was the idea that the money— no one, comedians weren’t getting $50 million checks that I had heard of. I think it was the money and that at that time, the show was wildly popular and it was all of a sudden just gone.

And I gotta tell you the truth, when I quit, I thought, you know, maybe I’ll go back. But it took some time for me to realize, like, “Oh, I’m never going back.” Maybe like a year. And then I thought my career was over. I believed that for a few more years. So I went through the whole process of mourning the narrative that I had in my head of being a big star. And at that time, I was just back in Yellow Springs. You know, Yellow Springs is, “Welcome back, superstar.” I was like, oh man.

MICHELLE OBAMA: But it’s like, no, how are you really doing?

DAVE CHAPPELLE: Yeah, perfect. It took me, I don’t know, what do you think, Lane? Maybe 4 years to get over it. But man, imagine how liberating that is to believe that it’s over. And I got over it. And then I just went back to work. I still needed money. And I could still fill rooms up ’cause people liked the show.

I started back in comedy clubs. And then I did this big tour. And the tour was tough for me ’cause the show was like, it’s a festival thing. It was like a 5-hour show that I’d have to close. It was tough, but it got me back out there. And then when I left that big festival thing and just did my own thing, I was just in the pocket again.

And then like a few years after that, someone would call me and be like, “Congratulations.” “What? What?” “You just got Tour of the Year.” I’m like, “I did?” I would never even pay attention. And one time somebody called me and said, “Congratulations.” I was like, “For what?” They’re like, “You just made Forbes list.” And I was like, “What?”

And I looked, and ’cause I don’t just count the money as it comes in. And I looked and it said like Dave Chappelle made— I don’t know what it was that year. I’d made $8 million bucks. I’m like, “Oh.” And I looked and I said, “Well, who?” I was 10th in the top 10. And then I looked at the other 9 names and I’m like, “Ah, I should come back.” It’s like, I think I can do this now.

The Woman Behind the Man

MICHELLE OBAMA: Yeah, think like, eh. I wish Elaine was mic’d up now, ’cause I want to be like, what was he like during that period? Were you staring off into space and telling them, don’t talk to me? No. What were you like then? ‘Cause Elaine does not have a mic.

DAVE CHAPPELLE: She was the person that really helped me get over myself.

MICHELLE OBAMA: Let’s give a round of applause to Elaine.

DAVE CHAPPELLE: Girl. And I gotta tell you, especially if you want—

CRAIG ROBINSON: Nice move, by the way.

DAVE CHAPPELLE: Yeah, you know what it is, Craig. You know what it is. But you know, I think at that time, maybe I did— you almost have to fight the urge to feel sorry for yourself if you’re mourning your career. And she’s not that kind of person. She just always keeps it moving almost. I mean, it’s like too much sometimes, like, will you slow down? But she just, you know, and our kids were young, and so she was just like, come on, man, get over that.

Now I gotta tell you, a friend of mine that was famous passed away recently, and one of the things that he said as he was dying— and man, he knew he was dying— he said, I’ll never forget this. He said, “Man, I took myself too seriously.” And man, that really resonated with me ’cause that’s such an easy trap to fall for, and nobody sets that trap for you better than yourself.

So it’s good to have somebody that— I mean, not to say she didn’t let me mourn my career, but she also helped remind me that my life is about more than myself. And for someone that’s, you know, your wife, ideally the best time she’s at your shoulder. And for someone at your shoulder to remind you of that— and then I had to think about it like, well, I guess technically she lost the money too.

MICHELLE OBAMA: I bet she knew what number you were on the Forbes list. Yeah, she’s like, “$8 million, okay, check.”

Raising Kids, Parenting Philosophy & Life in Yellow Springs

DAVE CHAPPELLE: No, and you know what, we also always had what we needed. I never really worried about money. Now what happens is when a guy gets famous, they upgrade everything. That’s when they get a new wife and a new house and a new this and a new that. Man, everything the same, which allowed us to do stuff like this when we did get money. It’s like, you know, why upgrade our house when we can upgrade the town we’re living in.

MICHELLE OBAMA: You said something really lovely about Elaine because Elaine, you grew up in New York. You were a New Yorker. You’re not from Yellow Springs. This was new. But I asked you how she felt about moving here, and why you chose here. Can you talk a bit about— you remember that conversation, Dave?

DAVE CHAPPELLE: Yeah, I said something to the effect of— and it’s true— at that time, my idea was we should build a lifestyle that I can feel more secure in maintaining, so that I can be courageous. And she’s from Brooklyn. She didn’t have any friends out here like that or any of that stuff. And we moved down here, and at first it was just me and her and our kids. And that’s, I’m sure that’s tough, giving up your social life.

New York City in and of itself, if you live in New York, it’s hard to live. I mean, I’m from here, and it was hard to come back here after living in New York. But she did it, man. She learned her way around. She found everything that she wanted. And eventually, as the years went on, she made her life here. She has friends and I have friends, but she was a pioneer.

And even now, I’m more inside. A lot of people in the community don’t reach out to me directly. They go through her because she’s— A lot of head shaking here.

MICHELLE OBAMA: Everybody like, yeah, Dave, you can’t count on Dave for nothing.

DAVE CHAPPELLE: No, you can’t. But she’s outside and she’s a very kind person, but she can also hold a line because everybody asks us for everything. And it’s part of being in a community. Everyone’s like this, but she’s been amazing at helping me do all of the things we’ve been doing in the community and having a relationship with the community. When I go travel, she’s the one that tells me what’s going on in town.

Dave the Father

CRAIG ROBINSON: Well, you’re a father of 3. What’s Dave the father like?

MICHELLE OBAMA: Can we get the mic too?

DAVE CHAPPELLE: You know, if my kids were vegetables, they’d be organically grown. I don’t know.

MICHELLE OBAMA: That’s got a big definition in the organic community.

DAVE CHAPPELLE: Okay, well, meaning number one is with the soil, which would be Yellow Springs. This is the place where they can independently learn to be courageous and like I learned before them— no offense again— to not be afraid of white people.

My kids are, unlike me, they’re mixed race. Their mom is Asian, their dad is Black. But their generation, I don’t think, thinks of anything like that. In a town like Yellow Springs, a young person can use their time more the way they want to because it’s not some of the immediate dangers. And it is a community. If my kids are messing up, somebody in town tells me, “Hey, I saw your kid doing this or that.”

But my parents weren’t heavy on rules. In fact, looking back, and I hope this doesn’t upset you, Mom, I looked at my parents as reference books. You get the most out of them if you’re interested. My mother has amazing stories about her life. My father would tell me amazing stories about his life. But they also gave me a weird context about my life. They didn’t police me as much as they guided me or horsewhipped me. I would think it was my idea. But it was them.

And I think I parent in a similar style. I’m the invisible hand dad. I’m there. And I think my oldest son has figured it out. Everything, he figures everything out first. But he’s the one that uses the resource of me as like a wiser person than him the most. He’s the one that calls me just to chew on something. “I’m trying to figure something out. What do you think of this? What do you think of that?” I don’t know, but we’re all happy. We laugh together.

What Parenting Has Taught Dave

MICHELLE OBAMA: What have you learned about yourself being a parent?

DAVE CHAPPELLE: That’s a great question.

MICHELLE OBAMA: Another one. Yeah, man, it’s like— I think I’m keeping count.

DAVE CHAPPELLE: That was 3. No, it’s— and I don’t mean it in the Meet the Press, “Thank you for your question, Scott. Yes, sir.” What have I learned about myself? Probably that I’m more courageous than I believe myself to be.

And also being a parent, you gotta, again, like Elaine, you gotta forgive yourself or get over yourself. And I think that being a parent for anybody is very humbling. But if you have all the money in the world, it doesn’t make you a good parent. In the beginning, I’d think, “I gotta provide for my family,” and all that stuff. But I’ve realized my time was way more valuable than I ever understood when I had 3 people that needed it.

And I learned that I’m a happier person than I thought. And really, COVID was when I really learned that, because we were all like trapped in our choices. And I remember at one point just being in the house like, “This is not that bad. I like these people.” Everyone’s comfortable. It was safe. And I could walk around town, and we’d all be going through COVID together, and I recognized everybody.

And then all those choices that I made, like moving to Ohio and stuff, that people laughed at me about— now I felt vindicated about each and every one of them. Because the world shut down and just for a minute I’m absolutely right, and it felt great.

Do His Kids Think He’s Funny?

CRAIG ROBINSON: Do your kids think you’re funny?

DAVE CHAPPELLE: Oh yeah. Oh yeah. Maybe not around the house, but I remember when they were kids, we were talking about Tyrone Biggums earlier, and that was the first time they were in the backseat, cracking up laughing, watching something on iPads. I said, “What y’all laughing at?” And it was that Tyrone Biggums sketch. And I was thinking in my mind, I told you that poop was funny. Spanned generations. Renee. Renee. Told you that s* joke would work.

I don’t know. It is humbling having kids. And I see time on them, as they grow and become. And it is just like, whew, it’s so precious.

MICHELLE OBAMA: Isn’t it fun watching them become people? Right before your very eyes. And scary. Oh my God, the most terrifying thing. So I tell people, it makes sense not to have kids. Absolute complete emotional sense. Don’t do it.

DAVE CHAPPELLE: And you know what’s funny, I think now with AI and all these things, I don’t know what you would tell a kid about how to prepare for the next 10 years, like what kind of jobs there will be or how those jobs will be done. What does a lawyer do in the AI age, or any of us? It’s interesting. But I’m amazed at how sophisticated the kids’ minds are, that they can sift through an avalanche of information. I’ll send them videos and they’ll be like, “Dad, that’s not real.” And say, “I don’t like Saweetie.”

Raising Kids in an Uncertain Future

MICHELLE OBAMA: I think I’m getting that a lot. I am so foolish. I believe all this stuff. It’s a shame. But it’s also a reminder of why we have to train them up and move out of the way. I mean, it’s the organic parenting piece of it. We’ve got to trust that they have to find the courage now to figure it out. It’s not our courage anymore. We can’t supplant our courage for theirs.

And these times are going to play themselves out. I mean, we’re moving into something that we don’t understand. We don’t know AI. We can’t figure it out. And it may seem scary now, but we have to have faith that they will figure this out and be able to tap into the values that we’ve instilled in them in communities like this, that they’ll remember humility and boundaries and love and trust. And all of that compassion has to go into whatever the solution is.

DAVE CHAPPELLE: That’s right. You know, a big part of their lifetime— my kids— maybe my daughter’s entire lifetime. I was trying to explain to somebody, I’m like, my daughter is 16, so Donald Trump is like the first white president she’s ever seen. I know, right?

MICHELLE OBAMA: Yeah. I know, right?

DAVE CHAPPELLE: Yeah, and my baby’s like, “Oh no, they’re not good at it, Daddy.” It’s a hard job.

MICHELLE OBAMA: It’s a hard job.

DAVE CHAPPELLE: Try to tell the people. It’s a hard job. It looks hard from the outside.

A Tribute to the Obamas

To that end, just so I make sure I say this— your family was so incredibly graceful. This is a long way to go, but you know what reminded me of seeing you guys is that Black dude on that Artemis ship. You remind me of that. You experience something. You’re in a social space program. And it’s so sequestered, and you see all these amazing things and come back and you share all that information. But whatever you had to go through to get in that spacecraft and to pilot through all of that.

As I go on in public life and see more, I have a greater appreciation of what I saw during the presidency. And you use the word I always think of— you in particular, I believe, did more to humanize what a presidency is than maybe anybody ever. You’re the first person that I feel like I could know that’s been in that space and survived it and came out as gracefully as you went in. So I really, really, really appreciate you and your family and your friends. Thank you.

Where Are We Now?

MICHELLE OBAMA: Well, I wanted to ask—

CRAIG ROBINSON: Go ahead, you ask and then I’ll go.

MICHELLE OBAMA: What do you think, how do you feel about where we are now in society? Just some Dave Chappelle thoughts about—

CRAIG ROBINSON: And while you’re thinking, please know that your voice means a lot to a lot of people our age and younger. Because I’ve got 4 kids and they range from 34 now down to 14.

MICHELLE OBAMA: He’s the head of the ODC, the Old Dads Club.

CRAIG ROBINSON: I’m the head of the— actually, I am the vice chair. So there’s one guy who is above me, but your voice carries a lot of weight. I personally could hear it every night.

DAVE CHAPPELLE: Oh man, thank you, bro.

The Power of Gathering and Living Small

DAVE CHAPPELLE: It’s funny, last week I was in LA and I performed at a nightclub on Ventura Boulevard I’d never been to. This for me is a big treat if I get to test drive a new venue, and I love the club. I think it’s called — what’s it called? Baby Katie’s, I think it’s called. Shout out to Katie’s, this great, great room.

But I bring it up because on a night like that, I’ll try out mostly new jokes just to see where I’m at and where people are. And you’re right, people — it’s not that my voice is important, but now it’s like somewhere the crowd is coming almost like church. They’re not coming to hear me say anything important, but they’re coming to lay down a burden, so to speak. And so a show like that was incredibly fun to do.

But what it tells me about where people are — and remember, this is in North Hollywood, so everyone’s doing pretty good out there — is that these times are uncertain, that there’s an emotional content or pain, or some people come to counteract a numbness. They just want to laugh so they can feel something. But it’s never really been quite like this before, where everyone feels like we’re on the precipice of some amazing change. And every day the new cycling is more appalling than the last day, and this doesn’t seem like it’s ever going to end. And every week I learn some new word like Strait of Hormuz or blah blah blah. And it’s such an avalanche that it is fun, even for me now, to watch comedians contextualize this stuff.

Someone asked me about my transgender jokes. They go, “You know, you got in a lot of trouble for those transgender jokes.” And I go, “Ah, the good old days.” ‘Cause so much has happened so quickly.

But, okay, I’m hopeful. As a matter of practice, this building opening up and being completed, that makes me hopeful. Having my own comedy club finally after all these years, that makes me hopeful. You guys being here with us, it’s like a dream come true. It makes me hopeful. My community coming together in tough times. Our family, we had tremendous losses recently. People in our family passed away. And the community picked us up. That made me hopeful.

The little things mean so much more now. And I want to remind anybody that’s listening to this show, man, that smile that you must have when it hurts to smile, this is priceless right now. Anything you can do to let each other know you’re safe or that you’re okay, it means everything right now, ’cause otherwise this is intolerable. It’s insufferable, what’s happening right now.

MICHELLE OBAMA: Thank you. Thank you. But I’m hopeful too. And this day with you, with this community here in this space gives me a whole lot of hope. As my husband says, we have overcome worse. But we overcome it by pulling together and not feeding on each other. That’s just the thing that we have to remember.

We have to remind our young people now because this internet kind of conversation, we’re playing in that space a little bit too much. And I don’t want young folks to get comfortable with that, that dissing mentality. Everything’s a diss record. Everything’s a diss. Negative algorithms. You just play in that space and you mistake those for real feelings and truth.

And this is what’s real, what you feel in the room when you’re with people. You were showing us the videos of the juke joint gatherings and the — the cornfields. People of all races and ages and with different cultural proclivities, all dancing to the same beat and smiling and moving together. That’s the power of gathering. The power of gathering is that we are reminded of our similarities and we forget the minor little stupid differences that is tearing this country and this world apart.

And I want more young people to fight for the gathering, fight for coming off of your phones, finding community, being reminded of who we are as people, and do not let the algorithm separate us from one another. That’s the danger of AI. But that’s in our control. That’s something we built.

Nostalgia, Analog Life, and Living Small

DAVE CHAPPELLE: I could text message, argue with an AI bot all day. Like if I thought it was a person, I would fuss with the thing all day. It does feel good to be outside. My son told me it’s a trend with him and his friends, like they ditch their phones just so they can be outside. My daughter got a CD player for her birthday and went through the roof because she couldn’t believe that she could hold the music in her hands. The kids are nostalgic for something that they haven’t really lived through or seen.

And I think we, the OGs, gotta let them know what an analog life feels like, how good an analog life feels. And I do think that pendulum will swing back, at least in the culture, somehow, as an elective. But yeah, I got the technology, I’m overwhelmed by it.

MICHELLE OBAMA: And I think the point that you — the decisions that you made to live in a way that allowed you to be courageous. Another way of saying that is to start out living small. We’re a culture where everybody is promoting, you start out big. Even watching HGTV, everybody wants big tray ceilings. They want the man cave. They want everything now.

DAVE CHAPPELLE: It’s like it’s your starter home.

MICHELLE OBAMA: Why does everybody think they deserve a granite countertop? We’ve lost the script. We grew up in a 1.5-bedroom apartment over our aunt’s house. My father got a new car occasionally. We got 3 gifts at Christmas. Our parents didn’t believe in stuff. And now everybody’s promoting the bling, the this, the that.

And look, there is nothing wrong with making a good living, with living well. But I try to tell my kids, learn to live small because you’re happier if you can live within a thing you can control. You’re not reaching for something that’s not even that important. That is not the thing that’s going to make you happy.

You asked what was it like living in the White House. It was a house, because that’s all a house is. What made it a home was what we brought to it — our love, the people we brought in it, how we opened it up, how we shared it with other people, how we made sure that we got every Black entertainer that would never get invited back in there, how we brought in Duke Ellington’s school, how we touched young people. That’s what made that house a home. It wasn’t the size of it, the color of it.

And that’s what I want young people to understand in this pursuit of fame and fortune. It’s a lie. We’ve lived it. That is not the thing that is going to bring you joy.

A Night at the White House

DAVE CHAPPELLE: That’s right. Yeah, to that end, I once got to go to one of your parties there. It was your birthday. One of the things that — okay, obviously I love smoking cigarettes. I asked somebody, “Where can I smoke a cigarette around here?” And one of the butlers took me down by the kitchen, and I saw your dog Bo getting walked. I’m like, oh, there’s that dog. I seen that dog on TV. And I’m like, can I get his autograph? They’re like, he bites. And the dog walked by.

And in the kitchen was like a jukebox kitchen. And I’m like, man, it’s the kitchen at the White House. And I said, I was wondering what they cooking in there. And I looked. Fried chicken. I said, man, it does feel like home. There was some greens, some fried chicken going. Lots of bacon. And one of the chefs was Filipino. I’m like, man, this is just like home.

CRAIG ROBINSON: We used to call those White House parties.

DAVE CHAPPELLE: Yeah, they were so good though, man. And that particular night was one of the last — actually, that weekend was the last time I’d ever seen Prince alive. And he was playing, and he was a surprise guest. I didn’t know he was there. And he came out, and as soon as he saw me standing out there, he was like, “Ah, I should have done that sketch.” It was so great though.

MICHELLE OBAMA: A lot of special nights.

DAVE CHAPPELLE: Yeah, a lot of joy. But one of the — I forgot to tell you this — one of the greatest highlights of my life. I’m standing there, I’m like, man, I can’t believe — and I’m shy. I was just standing in the corner, and I feel this hand on my shoulder, and I look over, and it was you. And you go, “Are you having a good time?” And I was like, I’m working. Way to go. Close them loops.

MICHELLE OBAMA: Way to go, man.

CRAIG ROBINSON: Well, Dave, talk about joy, man. You and this community have brought us a lot of joy. So thank you so much for inviting us.

Legacy and Community Investment

MICHELLE OBAMA: I do have one more question.

CRAIG ROBINSON: This is what she does. I know. This is what she does to me.

MICHELLE OBAMA: One more question. I know, but we talked about this. Because we’re on the same — you have invested so much in supporting this community. And we’re in the process of opening up our Presidential Center in June, on Juneteenth, by the way. So I know I’ve been spending a lot of time thinking about what his legacy, what does it mean? How do you think about legacy and your legacy in particular?

DAVE CHAPPELLE: Well, okay, first of all, that’s not apples to apples.

MICHELLE OBAMA: But I mean, okay, but the goal is the same. We’re opening up this center on the South Side of Chicago for a reason, because it is our community, it is our place. In the same way we’re making that investment. I think it’s maybe red apples to green apples.

The Weight of Legacy and the Value of Memories

DAVE CHAPPELLE: I think recently, because I’m getting older and I lost friends, the worst part of getting older is you start getting those phone calls more often. And I don’t think he would mind me saying this, but last week when I was in LA, I hit up Eddie Murphy out of the blue. And it’s not something I do often, but when I do it, it’s almost just because, could I just call Eddie Murphy? And it turns out I could. And I said, “You mind if I just stop by? I want to just talk to you for a little while.” And he was like, “Sure.”

And I went by and I didn’t realize it was his birthday, or the day before had been his birthday. Eddie’s got a beautiful house, obviously. He’s a family guy, so we’re sitting on his back patio and the music in the background is his grandkids joyfully playing in his pool, and he was wistful. And we’re talking, and I realized that it’s the first time since his brother passed that he and I had just spoke about Charlie or things like that.

And this is to the legacy part. And I say, “Hey, can I use your restroom?” And I walk into the restroom, and I saw a picture of Eddie holding his Mark Twain Prize. With your husband, and it was prominently featured in his home. And then I’m like, man, I would wear that as a t-shirt, I’m thinking to myself.

And then it’s going to sound weird, but it dawned on me, like, I’m Dave Chappelle hanging out with Eddie Murphy on his birthday. It’s just two of us, and that’s important.

Another time I chased Bob Dylan down for a meeting, and when he got there, he don’t know me at all, but I guess someone told him, like, you should meet this guy. And he was like, yeah. So he goes, “Yeah, man, what are we talking about anyway?” He was real standoffish. And I just kept asking him questions, and it took him a while to realize, like, oh man, he just ain’t want to know about stuff. And I’d be like, “What about the ’60s?” He goes, “Man, I don’t want to talk about the ’60s, man.”

But by the end of it, Bob Dylan was explaining to Dave Chappelle what Lenny Bruce was like. And so when I think about legacy, it’s always in these moments where I meet the first Black First Lady of the United States and her brother. And I’m like, simple as these meetings are, they’re important. They happen.

Coretta Scott King went to college here, and then she went off and married Martin Luther King. And a few years after she graduated from Antioch, her husband came back with her and they did the commencement address at Antioch College. And that’s just, at the time it was just another day in Yellow Springs, but now, I’ve never met any of these people, but I know Antioch, and it’s our history.

So I think the buildings encapsulate the message of what our lives have been, that you — I’ve got to spend all day with Mr. Robinson and Mrs. Obama, and I feel like I’ve known you for years. I feel like when you speak of your mother, I can just see her as vividly as — and it makes me want to smoke. But as simple as it all is, what you’ve accomplished with your life and how you’ve gone about it will very well live far beyond our bodies.

So for me, more than money or anything, I hoard memories. Today is like a memory. I’ll close my eyes and I’ll treasure the day for the rest of my life. Even if we became the best of friends, this time was such a special time to be together.

Mindfulness, Growth, and Moving Forward

DAVE CHAPPELLE: I also look at it like when I meet people, I try now — and it used to not be like this — but I try to remember it by myself. Because I had made fun of a comedian once, who’s younger than me, just busting his balls. But he got really hurt and he did all this press about how bad I was. And I was mad at first. And then I called him up like, “Why you say all those things about me?” He said, “Well, you forgot that you said this and the other.” And it dawned on me like, “Oh.” It never occurred to me that this person might look up to me. It’s just another person I’d see at the comedy club. So now I’m more mindful in that regard.

One day at a time, one foot in front of the other. I look back only at the places where the treasure’s buried, but I don’t look back at all the shadows and the scary faces. And I just try to, you know, I’m just hoping that my legacy is something like that applause break Richard Pryor got in Newark.

MICHELLE OBAMA: Well, you’re well on your way, for sure.

DAVE CHAPPELLE: Thank you. Thank you. Man, what an honor. Thank you.

MICHELLE OBAMA: It’s been a special visit for us, really. It really has. You all should be proud of the community you’ve built, all of you.

DAVE CHAPPELLE: My man, appreciate you.

CRAIG ROBINSON: Appreciate you, man. Thanks for having us. I guess I have to officially close it out now. So we really appreciate it, man. And it’s been a wonderful couple of days. And thank you all for being so welcoming to me and my sister and our colleagues. It’s been absolutely wonderful, man.

DAVE CHAPPELLE: Craig, don’t be freaked out because I know you don’t know me that well, but you’ll see in time. I love you, Craig. I love you.

CRAIG ROBINSON: Yes, sir. I love you, Dave.

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