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Dave Chappelle
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? I'm good, man. And he would look at him and be like, now, how are you doing? And then they. Well, you know, then they. 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 COVID And, man, I learned so much from so many unlikely people, so. And then, of course, I take those lessons around the world and make millions and millions of dollars.
Michelle Obama
This episode is brought to you by Chase Home Lending.
Craig Robinson
Hey, little girl. How are you doing?
Michelle Obama
Well, I'm doing just fine. We've got a special episode ahead. We are out of the studio, and we are in Ohio, in a beautiful town,
Craig Robinson
Yellow Springs.
Michelle Obama
I was gonna. You know, she was sitting here. Our guest is not supposed to be here, and he's not supposed to be talking, but I think he failed the first test.
Craig Robinson
He's not supposed to be here.
Michelle Obama
But it's good to see you. I haven't seen you in a couple of weeks.
Craig Robinson
I know it feels like months. I haven't seen you.
Michelle Obama
It has been months since.
Craig Robinson
Now that we've been doing this podcast, I get to see my lovely sister at least once a month. But I've been really busy the last couple of months, and she's been vacationing in Hawaii.
Michelle Obama
I haven't been vacationing. That's where I live, you know? See, this is how I mean, dude. You know, I work almost every day. Almost.
Craig Robinson
Do you?
Michelle Obama
No, not really.
Craig Robinson
That's what I thought. But we have a special guest.
Michelle Obama
We do.
Craig Robinson
And we should do a proper introduction.
Michelle Obama
Okay, take it away.
Craig Robinson
And I know this will sound familiar, but we've got Dave Chappelle, who is. I am such a huge fan of Dave Chappelle, and I'm gonna read him his bio. But I wanna tell you two things about meeting him for the first time. One is, Dave Chappelle is one of those people who makes me laugh just by thinking about him. I can think. Or someone says, dave Chappelle, and I'll start giggling. And I'm gonna tell. I mentioned this to Dave in the car or when we were around. Everybody knows Dave smokes.
Michelle Obama
No,
Craig Robinson
I hadn't smelled smoke since our mom passed away. And it was such.
Michelle Obama
Our mom smoked, by the way.
Craig Robinson
This was weird, but our mom smoked. And being around Dave gave me this warm feeling, that nicotine love of being around my mom.
Michelle Obama
Yeah, he Told me that this morning, and I was like, really? You really want to tell that story?
Craig Robinson
I am, I am. Because I think people relate to something like that.
Michelle Obama
Okay. All right, well, let's introduce Dave. Come on, Dave.
Craig Robinson
Dave Chappelle is one of the greatest comedians this country has ever produced. Full stop. Multiple Grammy Awards, the Mark Twain Prize for American Humor, the highest honor in comedy. A voice that has shaped culture, challenged power, and made the whole world laugh and think at the same time. This man is a legend. So it is a genuine joy, a personal honor for the both of us to introduce a man who is not only the most important artist of our generation, but a true neighbor to this community. O h, yeah. Y' all thought I didn't know about that, didn't you? Welcome. Dave Chappelle.
Dave Chappelle
Dave.
Michelle Obama
Dave Chappelle. Wow.
Dave Chappelle
Thank you, Dave.
Michelle Obama
Thank you. Thank you for inviting us here to Yellow Springs, your home, the tour. As Craig was saying, we got in our cars, there were about eight of them, and we drove around and we saw all the wonderful sights. Had the opportunity to stop by your mom's house. Dr. Sian, thank you. Just a beautiful, beautiful. Why was it important for you to have us here?
Dave Chappelle
Well, you know, being yourself, being Michelle Obama, I'm sure it's not lost on you that this community feels seen by the world. If it's seen by you. And unbeknownst to you, maybe, you know, this community, you have an enormous amount of support. You know, Ohio elected your husband twice in here locally, you know, the message of hope and change resonated profoundly. And I was telling you earlier, and I think you guys would agree, when Obama was running for president, it felt as if he lived in Ohio. Cause the presence of his ground team was so strong. And this radio station is our community's lifeblood. To us, it's our connective tissue. And we got close to losing them to Dayton, Ohio. And we were able to work things out and get this building built. And this is the first time I think this room has ever been used in any actual recording capacity. And, man, I can't think of a better way to inaugurate any room. But with you and your brother here amongst us and our friends and family. And it means the world to us. It means the world to me. But all of us, I can say without a doubt, are elated that you're here.
Michelle Obama
There was. Driving around, I told you, I got this familiar sense. I mean, one of the greatest privileges of my life was not just serving as first lady of this country, but getting to campaign throughout this country. 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. To people across the country, because in a time when we don't feel like we see each other, 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. I mean, it was oozing in every stop that we made. And I think it's important for our listeners to understand that 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.
Dave Chappelle
Oh, absolutely.
Michelle Obama
Or you've had your connection to Yellow Springs. Can you talk to us about why this community is so important to you?
Dave Chappelle
I think my presence, my family's presence in this community is an extension of, like, my father's life work. He lived here all 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 Christmas time 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. Very right. But this town is white. And I would come out here and play DC Records for them, and they'd be like, what is this music? And then I'd go home, play rock and roll stuff in D.C. and they'd be like, what is this music? But 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 gonna sound weird here, but it made me not afraid of white people. So in comedy, in, like, say, the 80s, really, the 90s, comedy circuits were segregated. And people don't know that 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, but for just like 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. Cause he said it, it would offend his audience. It's like, dude, it's Washington. Right, right, right. But I always played anywhere that anyone would listen. And I didn't realize till 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, like, 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.
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? 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 five, but they split up when I was two.
Michelle Obama
What did your mom refer to your dad as? The gentleman.
Dave Chappelle
The gentleman that I married. We went to my mom's house today and she said, yes, my ex husband used to live around here.
Michelle Obama
She's like, she didn't even say ex husband.
Craig Robinson
No, she said, the gentleman I was married.
Dave Chappelle
The gentleman I was married to. That's married.
Michelle Obama
It's like, oh, okay, sounds like your dad.
Craig Robinson
Yeah, 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. Well, 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, say this, mom. I can see exactly why they fell in love. And I can see why it wouldn't
Michelle Obama
work exactly like time.
Dave Chappelle
Let's call this, 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.
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 gonna 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.
Michelle Obama
You know, yeah, we know. We know.
Dave Chappelle
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 Ellis Springs. And so I came home for Thanksgiving, and I found out that my father's widow wrote the policy.
Michelle Obama
Wow.
Dave Chappelle
He was alive at the time. And I asked him like, yo, gentlemen, 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 them correctly, no one should see you make them. Oh. And they. And, you know, as odd as it sounds, it worked. The problem was that people on the campus, there was, like, an astronomical amount of sexual assault accusations. And she says, 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 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 because I'm working.
Michelle Obama
Thank God.
Dave Chappelle
If she sees me writing something down, I've already done the whole thing.
Michelle Obama
I'm gonna try that with Barack. Don't bother me working.
Dave Chappelle
It is like that though. I just feel it.
Michelle Obama
Be like you can blame Dave for that.
Craig Robinson
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Dave Chappelle
gonna say I get up at 4am and stare off in the space.
Michelle Obama
Staring off in the 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. You know, 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 because 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. If something bad would have happened to him, I miss not liking. Man, I would love to fight with this person or cold or cold shoulder person. But it's that kind of culture and you Know, like, I'm not that old, 50 years old, but there's a whole generation of kids that I watch go from, like, nothing to adults to, like, strong, really wise adults. It's just. 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 because 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. It reminds me to be the same. And then when I go out in the world, I can be more courageous because I know I have a place where if I completely wiped out and came back here, they'd just be like. They'd all smile, good morning, even though they knew our wife. And I'd be like, hey. And that's just why I love it here.
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, you know, we. We're striving for fame, for notoriety, for all the wrong things. And the truth of the matter is that life is about that small stuff. 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. 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, you know, this Is not my case. But it's not authentic. Your life, you know, the yes people or whatever the cliches 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.
Michelle Obama
They just don't.
Dave Chappelle
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 gonna forget how much you need to just talk to people. I used to shadow my dad around town, and he had this thing he would do. Not with everybody, with certain people. Hey, how you doing? I'm good, man. And he would look at him and be like, now how are you doing? And then they. Well, you know. 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 COVID And, man, I learned so much from so many unlikely people, so. 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.
Michelle Obama
You don't know. Shouldn't be a surprise to anybody. You know, Dave, you're not just one of the funniest people out here, but you're 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.
Dave Chappelle
Mom is.
Michelle Obama
Can you talk a bit about her? Your relationship with her, as you said earlier? What did you say? She championed you. You had a way to.
Dave Chappelle
I said, she put that battery in my back.
Michelle Obama
That's. 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 gonna sound arrogant, but it's not as arrogant as it sounds. Almost, but not quite. You 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. Don't want to be noticed because there's a target on you that comes with that. And my mom kind of put the soul in my back. Or if someone said. Or else, my mom would teach me and say, or else what? You know what I mean? Just ask or just move or just take the step if you feel. 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 broad of, like, just shame and self loathing a lot.
Michelle Obama
And how did she do that?
Dave Chappelle
How did 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. Okay.
Dave Chappelle
Yeah, but for real. She taught me. This is gonna sound. It's not gonna sound. I can't explain this, but she taught me how to not be afraid of getting in trouble. Cause she was my authority figure.
Michelle Obama
So you're his problem.
Dave Chappelle
Yeah.
Michelle Obama
No, I'm just kidding.
Dave Chappelle
But she was a lover. 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
The young people. Don't we snap for this?
Dave Chappelle
Yeah, yeah. The rules had reasons. I know you know about that. I see an activist in the front row.
Michelle Obama
Well, 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 father that poured into us. But a big thing was. I talk about this all the time. Our mom loved our voices, you know, I mean, she just loved our dirty drawers and loved everything that came out of our mouths. And she was interested and curious. 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, like, 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. What I remember is it didn't matter how ridiculous the things we said. 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. What I think gave me the confidence to be intellectual and successful that way.
Dave Chappelle
And you was outside of Chicago, intellectual?
Michelle Obama
Oh, yeah.
Dave Chappelle
Were you ostracized? No disrespect, but you were renowned nerds, both of you.
Michelle Obama
No, you had to learn how to. 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
Everybody loved you.
Michelle Obama
Oh, my God. He just.
Craig Robinson
Just played every sport and throw out the N word every now and then.
Dave Chappelle
Yeah. Oh, yeah, it works.
Craig Robinson
You know, that.
Michelle Obama
That always show that he's hard.
Craig Robinson
Show that. Show that I'm a little hard. But. But don't tell my mom I said that.
Dave Chappelle
You didn't have to fight. Cause you were a baller. Everyone loves ballers.
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. Cause you're bigger than everybody.
Dave Chappelle
Oh, man. My mom was like, you better bite, nigga. You better fight. See,
Craig Robinson
if your mom was at my house, there would have been a couple asses.
Dave Chappelle
What the heck going on? But you know what else it was about you mom that I love is. Okay, my mom's laugh is like music. If she, you know, and her mom's laugh is like music. And my grandfather, her dad's laugh is 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 or some kind of equivalent of like, yeah, I'm just 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 gonna be a doctor. And I showed the guy the book report, and he goes, man, he goes, that's good. I'm gonna be a doctor. He goes, nah. He said, Cause I was cutting up all day. I was 8. He said, you're gonna be a comedian.
Craig Robinson
Wow.
Dave Chappelle
And I go, what's that? He said, oh, you know, like Red Fox or Richard Pryor. You know who that is. I'm like, yeah, yeah. I watched, 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 gonna be one of those. And I thought about that. I think about it every once in a while. I'll think about. Because, 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 stand up, you know, to me, it feels like a lifetime. It was only six years, from eight to 14 when I started. Fourteen?
Craig Robinson
Yeah.
Dave Chappelle
Which didn't seem crazy at the time.
Michelle Obama
Yeah.
Dave Chappelle
Yesterday I got a text message from a comedian I started out with. He's kind of a famous guy. Patton Oswald. Yeah. Yeah. He. He sent me a. 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. Was it in D.C. on 14th? Now, 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.
Craig Robinson
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Michelle Obama
There are a lot of creative kids in communities across the land being a creative going to do show business. I mean, for most black parents, they'd be like, you better get you a good job. What are you talking about?
Dave Chappelle
Yes, exactly.
Michelle Obama
You know, but your, 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. yes, she was.
Dave Chappelle
I think. 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,
Michelle Obama
we'd eat fries, we'd go to the comedy club.
Dave Chappelle
After she had been working and 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 gonna be a famous comedian, but at that time, the crack epidemic and everything, all the bad Things like, could be doing. And I expressed such this earnest interest in being a comedian. And so she shepherded me. She figured out who's trustworthy and not trustworthy and, okay, you, 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. I would get gigs and make money and. And. And I didn't need her to go as much. And then that was kind of sad. Cause 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, like everyone says.
Michelle Obama
So, Dave, way to break the break the cycle of education.
Dave Chappelle
Someone needs to break this cycle of learning. But I ended up moving to New York. And honestly, honestly, maybe with the best education 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.
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 Dec. 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 these were all local guys. So I wasn't on the road yet. I would get a road gig here or there. And the principal at Ellington used to give me excused absences if I left on Friday to go on the road, because it was an artistic pursuit, not just 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.
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 you know, taking us full circle. Did you have to become that? Did you know that as a kid, that. That, you know, that's how I want to make people laugh?
Dave Chappelle
That's a very good question.
Michelle Obama
Thank you.
Dave Chappelle
No, no, that's, like, a very good question. There are certain, you know, 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, man, any night, it could be just some guy who just says the thing of that night. But, man, 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 call back a joke, make reference to something they referenced before, I'm like, wait a minute. You do the same joke twice? And from then on, man, 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. I don't want to play the same stuff everybody plays. But that being said, man, in my life, man, 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, please?
Michelle Obama
This is. This is your interview, Dave Chappelle. Please take your time.
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, like, I eyeballed 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, because 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. Man. Man. 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 at crowd and he goes, look. He goes, I want to do this for you guys. But he goes, I'm not feeling well. He said, I'm sorry. He goes, I don't got it in me tonight. I'm sorry. Just like that. And, man, you could hear, like, a pin drop. And then this guy in the back of the room jumps to his feet like that. He jumps up. He goes, we love you, Richard. And the place exploded. Longest, loudest ovation. Like, man, it went on and on. And he stood there, and then, okay, I'm young, right? But then I realize 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 bouncing off the walls. Like, man, they love this person. And if I had never seen that, I wouldn't even know that. Something to want, because no one has a language 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 at that moment.
Michelle Obama
So then, what does it feel like when it doesn't work
Dave Chappelle
now? It does now, man. Okay, this is a good question. You mean, like, if I do a show and it doesn't go well, you
Michelle Obama
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.
Dave Chappelle
And, yeah, maybe it's more like, in my experience, it was both, because 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, you know, 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, you know, most of those people who were critical of What I was doing didn't seem like they were of it. It's like 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 comics, 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'd be like, yo, put me up next. Cause I wanna say something about what they 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 or like, you know, nothing makes a comedian madder than reading his joke wrong in the paper, you know, and reading a joke is nothing like hearing one or being one. And the intention of a comedy show is a very unique intention. We are playing with the 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 gonna be good or even hopefully great, you gotta have a marginal error. And what they were doing was acting like thought or speech was binary. Like there's only. 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 say, yeah, but that's not what I was saying.
Michelle Obama
We talked about, you know, the first time I realized, oh my gosh, I'm in politics was, you know, 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, you know, we're all in the room together. You know, maybe the words wouldn't be exact. But we would all be able to feel it, you know, and that feeling wouldn't just be a small group, it could expand into a stadium, you know, 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
Right. Or even more insidious, trying to bend what you say to make it more interesting or salacious or. 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, it's, you know, 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. Right, right. And that's the skill, you know, 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. Like every room's a little.
Michelle Obama
Well, you said younger comedians are a little bit different because they're. They're not. Their audience isn't in their room.
Dave Chappelle
No, they're Internet people.
Michelle Obama
They're Internet people. And, you know, it goes back to, you know, the whole point of community. You know, it's like sharing a space with people is really important to connection and understanding. And it's no wonder. Why we feel so divided is 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 they're not in the room.
Dave Chappelle
A lot of them are negative, too.
Michelle Obama
Yeah.
Dave Chappelle
Cause that gets more engagement. If they talk bad about somebody, they'll get more clicks or more engagement. So everything's a diss record now. And it used to be. It's not like that.
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 the Chappelle Show.
Dave Chappelle
Man, that's the truth. I had one guy that I primarily wrote the show with, Neil 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. But guy gave us an idea. Oh, that's funny. We'll write it up. And if we used it, we pay him.
Craig Robinson
But it was known. That was the thing. I would have been submitting some stuff, man.
Dave Chappelle
It was fun. It was. But it. But it was my first time being corporately funny, and. And it got me ready for the next time because it was always a negotiation with the network. But I like in hindsight. Cause 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, man. But we went on Comedy Central and shot lights out. And I think the show was better on Comedy Central because there was an era of, you shouldn't be able to say these things. HBO look like you're just doing anything anyway. But on Comedy Central, that dance around standards and practices was joyful. And shout out to South Park. Cause I remember one time I did 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 the shit in the alley.
Craig Robinson
Yeah.
Dave Chappelle
And the Renee Standards in practice. This lady calls me upstairs and she's like, look, you can't have Tyrone take a shit in the alley. And it was gross, too. Cause we took, like, a Baby Ruth bar and, like, melted it. And then we just dropped it in the frame. It was really gross. And I was really funny. Really funny. She goes, you can't do that. You can't do that. And I go, I don't know. How about this, Renee? 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 kind of, you know, making room for everything. And to their credit, especially at that time, 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 convention. Chappelle's show was fun. Charlie Murphy. Oh, my gosh.
Craig Robinson
Yeah.
Dave Chappelle
Really? May he rest in Jesus.
Michelle Obama
Yeah.
Dave Chappelle
You know, I used to see Charlie Murphy in Hollywood at parties. I shouldn't say this, but one night I. Man, sorry, Mom. I was high on mushrooms and I went to some place.
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 high on mushrooms and ran into a personality as intense as Charlie Murphy. It's, like, daunting. He's got. He talks to his teeth and he. What's going on? And he's real gangster, 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'd always go, my brother. My brother this month. And if anyone said anything bad about Eddie at any point in his life, he'd smack the shit out of him. He loved his brother so much. Much. And. But what I learned that night, that I. Cause he was always a villain in movies. He was hilarious. He was like an artful storyteller. All the 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 with Eddie. And in the middle of lunch, he goes, someone said something about Rick James. And he said, man, I found fought Rick James on five 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 pulling, signing, like, man, can we do that on the show? He's like, wait, wait, you want me to beat up Rick James on the show? Like, not really. Like. And we just had him tell the stories and we dramatized them. And now you think, you know, and as we're shooting it, like, yo, this is like. Because we were on set dying, laughing. And then here's the kicker. And 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.
Craig Robinson
Yes.
Dave Chappelle
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, like, by his own account, he loved that sketch. So it's just one of those things where it's like. And the other thing about that Rick James sketch, last thing about it is Charlie made a show it to Eddie first. So I'd never been to Eddie Murphy's house, but we go there with his brother, and Eddie has this big screen and remnant 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 showed 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, 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 Capezios. That's what he said. And he gave us a green light, and he let us do it. And to me, it's one of the greatest sketches ever.
Michelle Obama
I mean, I think I watch that once a month. At least once a month.
Craig Robinson
Well, being from Chicago, the players ball. Oh, is lights out. And so accurate.
Dave Chappelle
You know what's funny? When people ask me what the. To me, that was my favorite day of shooting.
Craig Robinson
Really?
Dave Chappelle
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 wouldn't say it. Cause he's dead, but he. You know, and Kevin Hart and everyone get mad when I say that. Cause they love Patri so much, and I love him. I got there. But at that time, I was the guy to beat. And Patrisse 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, Patrisse 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, you go stay, 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
Get over yourself.
Dave Chappelle
He was that guy. And then that same week, I'm like, you know, we wrote the sketch. And I'm like, yo, let's call Patrisse. 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 very. Was a huge honor that he. That he cared as much as I cared. And, man, we were good. Up until Day 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 gonna say any names, but. Well, I think for me it was definitely Ellington. There's a vulnerability that an actor has to have that I don't know that comedians are necessarily vulnerable the same way. And with 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 Martinsville. Denzel Washington in Training Day is like watching the most 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. Cause he was vulnerable. Cat Williams is a guy. Every time I see him act, I'm like, man, he should do that more. Cause he's like. 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 was read books. And I can do it like, you know, but. But some people can. It's like music. Some people can just play. I don't know.
Michelle Obama
How do you feel like you tap into that vulnerability?
Dave Chappelle
Well, I. I do. I think I'm more vulnerable on stage than most comedians. You know, I'll say anything when people feel like they can't say anything, but. Which is a vulnerable position to put myself in. But some jokes, it's like, I just gotta. I just wanna see if it works. I don't wanna 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. Cause the audience is. Is also vulnerable if you're taking it out of bounds. Yeah, yeah. I don't know.
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 the country for a week or so.
Dave Chappelle
Elsie's gone for two 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. Comedians weren't getting $50 million checks that I had heard of. I think it was the money. And at that time, the show was wildly popular. And it was. All of a sudden it was just gone. And, you know, 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, Dave?
Dave Chappelle
Yo, Perfect for. Took me. I don't know. What do you think, Lane? Maybe four 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 because people liked the show. And 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 five 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? 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, he just made Forbes list. And I was like, what? And I looked and. Because I don't just count the money as it comes in. And I looked and said like, dave Chappelle made. I don't know what it was that year. I'd never. I'd made 8 million bucks. I'm like, oh, man. I looked at the. I said, well, who? I was 10th in the top 10. And then I looked at the other nine names, and I'm like, ah, I should come back.
Michelle Obama
It's like, I can do. I think I can do this now.
Dave Chappelle
Yeah, things like that.
Michelle Obama
I wish Elaine was mic'd up now because 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 now. 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, girl.
Dave Chappelle
And I gotta tell you, especially if you want.
Craig Robinson
That's smooth, by the way.
Dave Chappelle
Yeah, hell, you know what it is, Craig. You know what it is. But, you know, I think at that time, maybe I did. You know, 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? She just. 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, he said, I took myself too seriously. And, man, that really resonated with me because it'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, you know. 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 like, you know, your wife, ideally, the best times, she's at your shoulder. And for someone at your shoulder to remind you of that, and it's like, you know. 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. No.
Dave Chappelle
And you know what? We also always had what we needed. You know, 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. 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. Do you remember that conversation, Dave?
Dave Chappelle
Yeah. I said something to the effect. And it's true. At that time, my idea was we should build a lifestyle that. That I can feel more secure in maintaining so that I can, you know, be courageous. And, you know, she's from Brooklyn. She didn't have any friends out here like that or any of that stuff. And we moved out here and, you know, at first it was just me and her and our kids. And I'm sure that's tough, giving up your social life and, you know, and New York City in and of itself, if you live in New York, it's hard. Hard to live. I mean, I'm from here, and it was hard to come back here after living in New York. But, man, 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. We have, you know, she has friends and I have friends, but, you know, she was. She was a pioneer. And even now, like, I'm more inside and, you know, a lot of people in the community don't reach out to me directly. They go through her because she's a
Michelle Obama
lot of head shaking here. Like, yeah, Dave. You can't count on Dave for nothing.
Dave Chappelle
No, no, you can't. But she's outside and, you know, she's. She's a very kind person, but she's also. She can hold a line because everybody asks us for everything and, you know, it's part of being in a community. Everyone's like that. But she's been amazing at helping me do all of the things we've been doing in the community and, you know, having a relationship with the community. When I go travel, she's the one that tells me what's going on.
Craig Robinson
Yeah, well, you're a father of three.
Dave Chappelle
Oh, yeah.
Craig Robinson
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.
Michelle Obama
That's a guy. 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 a 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. Right. 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 there's not so many 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. Correct. But you know, my parents weren't like, heavy on rules. In fact, looking back, and I hope this doesn't upset your 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 horse whistled 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. You know, I'm there. And, you know, I think my oldest son has figured it out. Everything. He figures everything out first. But he's, I think, 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.
Michelle Obama
What have you learned about yourself being a parent? Yeah,
Dave Chappelle
that's a great question.
Michelle Obama
Another one?
Dave Chappelle
Yeah. Man, it's like.
Michelle Obama
I think I'm keeping count. That was three.
Dave Chappelle
Yeah. No, that isn't. I don't mean that in the Meet the President. Thank you for your question, Scott. What have I learned about myself? Probably that I. 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. You know, like in the beginning, I 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 three people that needed it. You know what I mean? So maybe that. And I learned that. Well, I learned that I'm a happier person than I thought. And really, Covid was when I really learned that. Cause we were all, like, trapped in our choices. And I remember at one point just being in a 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.
Craig Robinson
Do your kids find your humor? Do they think you're funny?
Michelle Obama
Do they think you're funny?
Dave Chappelle
Oh, yeah. Oh yeah. Maybe not around the house, but like. Like I remember when they were kids, we talking about Tyrone Biggums earlier and that was the first time they were in the backseat, like cracking up, laughing, watching someone on iPads, but y' all laughing at. And it was that Tyrone Bickham sketch. And I was thinking in my mind, I told you that poop was funny. Span generations.
Michelle Obama
Renee.
Dave Chappelle
Renee told you that shit joke would work. Yeah, I don't know. It is humbling having kids and you know, I see time on them, you know, as they grow and become. And it is just like. Is so precious.
Michelle Obama
Isn't it fun watching them become people?
Dave Chappelle
Yeah.
Michelle Obama
Right before your very eyes.
Dave Chappelle
And scary.
Michelle Obama
Yeah. 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
Yeah, that's right. And you know, it'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 aia, Joy? Or any of us? And I think, I don't know. It's interesting, but I'm amazed at how sophisticated the kids minds are that they can sift through an avalanche of information and they can say, I'll send them videos and be like, dad, that's not real and say, hi.
Michelle Obama
I'm like, so you know, I'm getting that a lot. I am so foolish. I believe all this stuff.
Dave Chappelle
It's a shame I the worst.
Michelle Obama
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 be. That's going to play itself 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. That compassion has to go into whatever the solution is.
Dave Chappelle
That's right.
Michelle Obama
You know?
Dave Chappelle
Yeah. You know, in the last 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's 16, so Donald Trump is like the first white president she's ever seen.
Michelle Obama
I know, right? Yeah, I know, right?
Dave Chappelle
And my baby's like, oh, no, they're not good at it. Daddy.
Michelle Obama
It's a hard job.
Dave Chappelle
It's a hard job. Try to tell the people it's a hard.
Michelle Obama
It's a hard job.
Dave Chappelle
It looks hard from the outside, but 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 remind me of seeing you guys is that black dude on that Artemis ship. You remind me of that. You experience something. You're like, 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 that 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 used the word I always think of you in particular, I believe did more to humanize what a presidency is than maybe anybody ever. That you're the first person that I feel like I could know that been in that space and, you know, survived it and came out as gracefully as you went in. So I really, really, really appreciate you and your family and your presence.
Michelle Obama
Well, I wanted to ask.
Craig Robinson
Go ahead, you ask, and then I'll go.
Michelle Obama
What's. What do you think? How do you feel about where we are now in society? You know, 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, you know, I've got four kids, and they range from 34 now down to 14.
Michelle Obama
He's the head of the ODC, the old dad's Club.
Craig Robinson
I'm the head of the actually I am. I am. I am the vice chair. 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.
Craig Robinson
Like,
Dave Chappelle
you know, it's funny. I think, you know, last. Last week, I was in la, and I. 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, like, a new venue. And I love the club. I think it's called. What's it called, babe? Katie's. I think it's called. So 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. So a show like that was incredibly fun to do, but 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. And every day, the new cycling is more appalling than the last day, and this doesn't seem like it's ever gonna end. And every week, I learn some new word, like straight of hormuz or buh, buh, buh, 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. Because 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, 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. Hopefully the little things mean so much more now, and I would want to remind anybody that's listening to this show, man, that smile that you must have when it hurts to smile 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 because otherwise this is intolerable. It's insufferable what's happening right now.
Michelle Obama
Thank you. Thank you. But, you know, I'm hopeful too. And this day with you, with this community here in this space gives me a whole lot of hope, you know, I mean, 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. 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 dissing mentality. What'd you say?
Dave Chappelle
Just, everything's a diss record.
Michelle Obama
Everything's a dis. Yeah, you just play in that space and you mistake those for real feelings. In truth. And this is what's real. You know, what you feel in the room when you're with people. You know, you were showing us the videos of the juke joint gatherings and the, you know, the cornfield. The cornfields. You know, people of all races and ages and with different cultural proclivities all dancing to the same beat and smiling and moving together. It's like that's the power of gathering, you know, 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. You know, fight for coming off of their 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, you know, that's. You know, but that's in our control. You know, that's something we built.
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. You know, 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. Cause 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, you know, the OG's gotta let em know how good an analog life feels, you know, And I do think that pendulum will swing back, at least in the culture somehow, as an elective. But yeah, 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. You know, another way of saying that is to, you know, start out living small. You know, we're a culture where everybody is promoting you start our biggest, you know, even watching hgtv. Everybody wants a big tray, ceilings, they want the man cave, they want everything. Now it's like it's your starter home. You know, why does everybody think they deserve a granite countertop?
Dave Chappelle
You know,
Michelle Obama
we've just lost the script. It's like, you know, we grew up in a one and a half bedroom apartment over our aunt's house. My father got a new car occasionally, you know, we got three 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, you know, living well. But I try to tell my kids, learn to live small because that's, you know, you're happier if you can live within a thing you can control. You know, 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? You know, it was a house, because that's all a house is. What made it a home was what we brought to it, you know, 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 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, you know, what I want young people to understand in this pursuit of fame and fortune. It's a lie. You know, it is. You know, we've lived it. That is not the thing that is going to bring you joy.
Dave Chappelle
That's right. Yeah. To that end, I once got to go to one of your parties there.
Michelle Obama
Yeah.
Dave Chappelle
It was your birthday. Yeah, we were talking about it.
Michelle Obama
Yep.
Dave Chappelle
One of the things that. Okay, you know, obviously I love smoking cigarettes. That's my mother. But obviously I asked somebody, I go, where can I smoke a cigarette around here? And one of the butlers took me down by the kitchen, and I saw your dog, Beau. Oh, yeah, like, 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 lights, and the dog walk by, and. And in the kitchen was, like, a jukebox kitchen. And I'm like, man, it's the kitchen at the White House. And. And I said, I just wonder what they cooking in there. And I look. Fried chicken. I said, man, it does feel like home. There was some greens, some fried chicken going. I said, man, lots of bacon. And one. 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, I should have done that sketch. It was so great, though.
Michelle Obama
A lot of special nights. Yeah.
Dave Chappelle
A lot of joy. But one of the. I forgot to tell you this. One of the greatest highlights of, like, my life as I'm standing, 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, closing loops.
Michelle Obama
Way to go, man. Oh, 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.
Michelle Obama
I do have one more question.
Craig Robinson
This is what she does.
Michelle Obama
I know.
Craig Robinson
This is what she does to me. One more question.
Michelle Obama
I know, but we talked about this. It's like, you know, we're. Cause we're on the same. You know, you have invested so much in supporting this community, you know, 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? I don't know. How do you think about legacy and your legacy in particular?
Dave Chappelle
Well, okay, first of all, that's not apples to apples, but, I mean.
Michelle Obama
Okay, but the goal is the same. I mean, 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, you know, So I think it's. Maybe it's red apples to green apples.
Dave Chappelle
I think recently, because I'm getting older and I lost friends, like, you know, the worst part of getting older is you start. You get 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? Turns out I could. And I said, you mind if I just stopped by? I wanted 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. You know, Eddie's 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 said, hey, can I use your restaurant? And walk into the restroom. I saw a picture of Eddie holding this 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. And it's gonna sound weird, but it dawned on me, like, I'm Dave Chappelle hanging out with Eddie Murphy on his birthday. It's just the 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, you should meet this guy. And he was like, yeah. So he goes, yeah, man, what are we talking about? Anyway? He was like. He was like real standoffish. And I just. Just kept asking him questions. And it took him a while to realize, like, oh, man, he just ain't wanna know him and stuff. And I'd be like, what about the 60s? He goes, Man, I don't wanna talk about this 60s, man. He would say, but by the end of it, you know, 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 a. The first black first lady of the United States and her brother, and I'm like, you know, as 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. And that's just. You know, at the time, it was just another day in Yellow Springs. But now, you know, 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. You know, I got to spend all day with Mr. Robinson and Ms. 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, 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 very well will live far beyond our bodies. And so, for me, more than money or anything, I hoard memories. Today is like a memory. Like, 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. So, you know, 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. Cause 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 do you say all those things about me? He said, well, you forgot that you said this, that, and the other. And I'm like. And then 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. So, I mean, you know, 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 look back at all the shadows and the scary faces, and I just try to just, you know, I'm just hoping that my legacy is something like that. Applause break Richard Pryor got in Newark.
Michelle Obama
Well, you. You're well on your way for sure.
Dave Chappelle
Thank you. 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 built. All of you. Thanks for having us.
Craig Robinson
Yeah. I guess I have to officially close it out now, so. We really appreciate it, man. And it's been. 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. Cause I know you don't know me that well, but you'll see in time. I love you, Craig.
Craig Robinson
I love you.
Dave Chappelle
Yes, sir.
Michelle Obama
I love you, Dave.
Dave Chappelle
It.
IMO with Michelle Obama and Craig Robinson
Guest: Dave Chappelle
Date: May 6, 2026
Location: Yellow Springs, Ohio
This episode of IMO features Michelle Obama and Craig Robinson in conversation with legendary comedian Dave Chappelle, recorded in the heart of his community in Yellow Springs, Ohio. The discussion weaves through personal histories, the power of community, lessons from family, the pitfalls of fame, legacy, and the urgent need for genuine human connection in an increasingly digital and divided world. With warmth, wit, and vulnerability, the three unpack how memories and relationships shape our sense of self and purpose.
"Everyone's as famous as I am here, we all kind of know each other... it's irreplaceable. It really does remind you of the value of people." — Dave Chappelle ([21:21])
"She put that battery in my back... she made me not afraid to be great." — Dave Chappelle ([26:22])
"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." — Michelle Obama ([88:49])
"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." ([96:56])
On Humanizing Greatness
"Sometimes you have to be a lion so you can be the lamb that you really are." — Dave relaying wisdom from his mother ([27:43])
On Community
"Life is about that small stuff. You know, it's the small connections that you make with people… you can't get that by holding a phone." — Michelle Obama ([22:39])
On Parenting
"If my kids were vegetables, they'd be organically grown." — Dave Chappelle ([73:55])
On Resilience
"Took me... maybe four years to get over it. But, man, imagine how liberating that is, to believe that it's over." — Dave, about leaving TV fame behind ([66:45])
On the White House as Home
"What made it a home was what we brought to it, our love, the people we brought in it, how we opened it up... 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." — Michelle Obama ([91:47])
On the Healing Power of Laughter
"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." — Dave Chappelle ([84:15])
This episode is a heartfelt, humorous, and wise meditation on what it means to live meaningfully in challenging times—with laughter, humility, and fierce love for family and community.