Have a Good Laugh with Jimmy Kimmel

On this week’s episode of IMO, legendary late night host and comedian Jimmy Kimmel joins the show! Jimmy opens up about his childhood in Las Vegas, shares why he was fired from every job he had before late night, and how he built his show from the ground up, family and all. Plus, he shares a recent not-so-proudest parenting moment. Have a question you want answered? Write to us at imopod.com http://imopod.com. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Craig Robinson?

  It was his 50th anniversary of the priesthood and they had a big, thousands of people came to celebrate in Vegas and they called me and they said, would you speak at this?

• 0:09Michelle Obama?

  I mean, that's just like.

• 0:11Craig Robinson?

  So I had a painting made of Father Bill to celebrate the occasion. And I had it on an easel and I had a, you know, a sheet hanging over it. I was going to reveal it. And I gave my, you know, I talked about our relationship and I made fun of him and it was bishops were there. And then I revealed the painting and it's a nude painting of him. Sitting on a stool.

• 0:43Michelle Obama?

  This episode is brought to you by Shift and Chase Home Lending.

• 0:49Craig Robinson?

  Hey, niche.

• 0:50Michelle Obama?

  Hi, Craig.

• 0:51Craig Robinson?

  How are you?

• 0:52Michelle Obama?

  That's a good jacket. Have you worn that before?

• 0:54Craig Robinson?

  I wore this to the Christmas party. I haven't worn it on an episode yet.

• 0:59Michelle Obama?

  That's cool.

• 1:01Craig Robinson?

  Yeah.

• 1:01Michelle Obama?

  It's cool on all fronts. The color is good. It feels smooth. Now can you get that in other colors?

• 1:07Craig Robinson?

  Yes, I have this in a different, I have a, I have a couple of these. Yes.

• 1:11Michelle Obama?

  Go on with your bad self.

• 1:14Craig Robinson?

  Yeah.

• 1:15Michelle Obama?

  Fly boy, fly boy. So what's new and exciting in Craig Robinson land?

• 1:20Craig Robinson?

  Not much. Uh, no, not much.

• 1:24Michelle Obama?

  Man, you're boring.

• 1:26Craig Robinson?

  You know, I, I will say, so this trip to LA has been great. Now the sun's back out. But I've been, I've been.

• 1:36Michelle Obama?

  Cramped up, cooped up.

• 1:38Craig Robinson?

  Cooped up. And, um, and this is a time when I really enjoy having my Airbnb be close because it was pouring rain the last couple of days. So getting here without getting my outfit soaked is, is easy.

• 1:56Michelle Obama?

  Uh, we were just talking about how many Airbnbs do you think you've stayed in since we, um, launched IMO? Because you're, you, you, you gets around.

• 2:09Craig Robinson?

  I, I do. And, and so we've, we've, I tried to figure it out. We've done 40 episodes, but you can't, you don't do one per episode.

• 2:17Michelle Obama?

  Right, right.

• 2:18Craig Robinson?

  You figure on average, we've done four or five.

• 2:20Michelle Obama?

  How many total tapings have we done?

• 2:23Craig Robinson?

  Yeah.

• 2:23Michelle Obama?

  In the last year team?

• 2:24Craig Robinson?

  And I'd say about. Ten tapings?

• 2:29Michelle Obama?

  Separate tapings.

• 2:30Craig Robinson?

  Because once we started doing this, then I was, just in my own personal life, I was doing Airbnb.

• 2:36Michelle Obama?

  Airbnb for all your travel, your trips, the things with the boys.

• 2:39Craig Robinson?

  The boys, all of that stuff. So I, I would say since last August.

• 2:46Michelle Obama?

  Mm hmm.

• 2:47Craig Robinson?

  So a year ago, August, probably 2025.

• 2:51Michelle Obama?

  But it has been a great year one, a season one, and we are looking forward to a great season two with Airbnb. Our partnership, we love it, love them, love the team of people who come with it, which is always a big part of it. Of course, Brian Chesky, the founder, the CEO, the big head honcho is a dear, dear friend and someone that I love and respect dearly. But that's no bias. I think if he ran a janky company, we wouldn't be using him.

• 3:20Craig Robinson?

  Right.

• 3:20Michelle Obama?

  But he just so happened.

• 3:22Craig Robinson?

  You've been using janky a lot lately.

• 3:25Michelle Obama?

  Loving the word janky. It applies to so much. Especially these days, there's a lot of jankiness happening around the world, but Airbnb doesn't fall into that category of janky.

• 3:36Craig Robinson?

  No.

• 3:37Michelle Obama?

  So, um.

• 3:39Craig Robinson?

  So I'm really.

• 3:40Michelle Obama?

  Janky, no.

• 3:40Craig Robinson?

  Oh, no, that's not right. We, we are.

• 3:44Michelle Obama?

  Our guest this episode.

• 3:47Craig Robinson?

  We are very excited about our next guest and, and

• 3:55Craig Robinson?

  I want to tell a little brief story before we bring him out because this whole time we were talking about how both of us have been on his show.

• 4:05Michelle Obama?

  Uh huh.

• 4:05Craig Robinson?

  That's never happened, right?

• 4:07Michelle Obama?

  No, because no one invites you on their show.

• 4:09Craig Robinson?

  Me anywhere.

• 4:10Michelle Obama?

  But it's like.

• 4:11Craig Robinson?

  Jimmy, when I did my book tour back in 2010, he invited me on. But my wife Kelly swore, who knows everything, swore that I wasn't on the Jimmy Kimmel Show.

• 4:22Michelle Obama?

  She thought it was the other Craig Robinson.

• 4:25Craig Robinson?

  I don't know what she thought, but I was like.

• 4:27Michelle Obama?

  How do you forget that? How do you confuse that?

• 4:29Craig Robinson?

  Who would forget being on Jimmy Kimmel's show? I mean, the green room aspect of his show, the music, I mean.

• 4:37Michelle Obama?

  It's a good green room.

• 4:38Craig Robinson?

  It was a real memorable vibe, as my kids would say. It was a vibe. It was drinks and food and music.

• 4:48Michelle Obama?

  Strippers, no, no, there weren't strippers. So that was only with me, right, Jimmy?

• 4:53Craig Robinson?

  So.

• 4:53Michelle Obama?

  The male strippers. I didn't tell Barack.

• 4:56Craig Robinson?

  But we, we, we, we were, you know, and I'm sure Jimmy wouldn't have remembered.

• 5:03Craig Robinson?

  If we were, if I was on, he would remember if you were on.

• 5:05Michelle Obama?

  Let's hope so.

• 5:07Craig Robinson?

  So Crystal was doing some research and found out right before we came on.

• 5:10Michelle Obama?

  That you were right.

• 5:11Craig Robinson?

  I was right.

• 5:12Michelle Obama?

  Yeah, I would like to think you would forget.

• 5:14Craig Robinson?

  To get home.

• 5:16Michelle Obama?

  And tell, tell Kelly that she was wrong. Well, let's properly introduce Jimmy Kimmel.

• 5:22Craig Robinson?

  Yes, let's do that. Jimmy Kimmel serves as host and executive producer of Jimmy Kimmel Live. Which has become a fixture of late night television over the past 23 years. In addition to his show, he is an accomplished producer and award winning host, leading numerous hit shows, specials, and major award shows. And you know a dude is hot when you got all of that.

• 5:51Michelle Obama?

  Oh, he's just hot because he's got those cute jeans on.

• 5:55Craig Robinson?

  Welcome, Jimmy, come on in.

• 5:57Michelle Obama?

  Hi, Jimmy, see, look, look how cute his jeans are.

• 6:01Craig Robinson?

  Good, I'm cute.

• 6:02Speaker 02

  Good to see you, man.

• 6:03Craig Robinson?

  How are you?

• 6:04Michelle Obama?

  Turn about, fair play, look, looky here.

• 6:07Speaker 02

  I'm excited to be here and thank you for saying my jeans are cute. I fretted over them before I came. My wife made me change.

• 6:14Michelle Obama?

  Tell her.

• 6:15Speaker 02

  She did.

• 6:16Michelle Obama?

  Did she really?

• 6:16Craig Robinson?

  Where is she? Why doesn't she do, why didn't she come?

• 6:19Speaker 02

  She's back with the kids at the house, but she told me, she said, looked at me, she said, when in doubt, just wear solids. And so I did, I went with solids.

• 6:28Craig Robinson?

  Did you have striped jeans on?

• 6:29Speaker 02

  I very much remember you being on the show. I remember it quite well. I remember we talked about coaching, we talked about your book, we talked about. So tell Kelly, you know, I don't always remember if people have been on the show or not. Sometimes it gets blurred, but I definitely remember that.

• 6:44Craig Robinson?

  Thank you, thank you for saying that.

• 6:46Speaker 02

  The weird, the thing that you might want to be concerned about is the fact that she doesn't remember.

• 6:50Michelle Obama?

  That's the thing, and Kelly, his wife remembers everything, so maybe.

• 6:54Speaker 02

  Except me.

• 6:55Michelle Obama?

  No, maybe she didn't remember him.

• 6:58Craig Robinson?

  Well, you know what it was.

• 6:59Michelle Obama?

  What?

• 7:00Craig Robinson?

  That was one of the shows where I came alone. Usually she would come with me. But I think I flew down, I was in Oregon at the time, so I flew down.

• 7:09Speaker 02

  It may have been a blind spot caused by jealous rage.

• 7:12Michelle Obama?

  That's right.

• 7:14Craig Robinson?

  There you go.

• 7:15Michelle Obama?

  We were asking, so you're, not sure when this is going to, but right now you guys are on a week hiatus.

• 7:21Speaker 02

  We're on a break, yeah.

• 7:22Michelle Obama?

  Yeah, yeah, yeah. How does, how does that work? I mean, it feels like this talk show thing is pretty grueling.

• 7:29Speaker 02

  It is. It's grueling.

• 7:32Michelle Obama?

  So, uh, what's the week break feel like? Are you like chilling? Are you?

• 7:37Speaker 02

  It feels brief. I know we did, actually, we rented an Airbnb in Phoenix.

• 7:42Michelle Obama?

  Really?

• 7:43Speaker 02

  We rented, uh, we went to visit our friends there. I have a friend named Chris Bianco, he's a great pizza chef. I think you've had his pizza.

• 7:50Michelle Obama?

  Absolutely.

• 7:51Speaker 02

  And, um, we rented a beautiful house. He brought his kids over and they all, they came and stayed and he got this, he got this El Camino restored. It took four years to get it restored. It was his 60th birthday present. We all chipped in for this. He, it took four years again, he's had it for six weeks. Uh, we're about to get in the car to go to his pizza place. He accidentally stepped on the, um, I don't know what exactly happened, but let's just say the car wound up in the Airbnb. We took out half the garage of the Airbnb.

• 8:25Michelle Obama?

  Oh my gosh.

• 8:26Speaker 02

  They were very nice about it, though.

• 8:28Michelle Obama?

  Oh, that's so, so much. Did he, did he, uh, uh, trash the car?

• 8:33Speaker 02

  The car is trashed. Our rental car was trashed. It was, uh, it was like a video game type scenario.

• 8:39Michelle Obama?

  Oh no, he was so excited.

• 8:41Speaker 02

  Yeah, he was. It was sad. It was sad.

• 8:43Michelle Obama?

  It is so sad.

• 8:45Speaker 02

  But I told him, don't, we're gonna look back and laugh at this.

• 8:48Craig Robinson?

  So, tell me this, did it have the old fashioned gear shift that was on the side where you had to?

• 8:52Speaker 02

  No, it had, it was down, uh, I, I know this because I drove it shortly before he drove it into the house.

• 8:59Michelle Obama?

  And it's so good.

• 9:00Speaker 02

  And I remember thinking, this car's too fast. It's like, it's too responsive, you know? It's a little bit dangerous.

• 9:06Michelle Obama?

  Yeah, but it has to be in the right gear. Gear.

• 9:08Speaker 02

  It does. That's one of the things that we learned.

• 9:10Craig Robinson?

  Yeah, so if you're in, if you're in drive and should be in reverse, it just doesn't work.

• 9:15Michelle Obama?

  So when that happens to your friend, are you laughing at him? Are you sort of like, oh buddy?

• 9:21Speaker 02

  You know, I felt bad for him. I did. I mean, it's, you know, when you, when something like that happens and then there's that moment of release where you realize, okay, nobody's hurt. And something ridiculous has just happened. I did have the urge to laugh, but I, I fought it.

• 9:39Michelle Obama?

  We are laughing now.

• 9:42Speaker 02

  He's probably still not laughing, but um.

• 9:45Michelle Obama?

  But maybe by the time this airs.

• 9:46Speaker 02

  Maybe doubtful, but maybe, yeah.

• 9:48Michelle Obama?

  Were the kids in the car?

• 9:50Speaker 02

  The kids were, you know, the kids were in our rental car and then the other group of kids were in the other car. And we had three cars and we managed to destroy two of them. We'll get the other one later.

• 10:05Michelle Obama?

  Did you get pizza at least?

• 10:06Speaker 02

  We did go, we did go for pizza afterward.

• 10:08Michelle Obama?

  Cause the kids were like, are we, cause kids don't care. They're like, well, we thought we were getting pizza.

• 10:12Speaker 02

  It is funny because there was no discussion of not getting pizza after. There's not even, not even a moment of that. We couldn't close the garage door of the house and we just left.

• 10:24Michelle Obama?

  So that's what you do on your break. Yeah, no wonder it didn't feel long. You were dealing with crisis. Yeah.

• 10:30Speaker 02

  We took the kids to Vegas. We had a lot of fun in Vegas.

• 10:32Michelle Obama?

  So your kid, the, the little ones.

• 10:34Speaker 02

  Yeah.

• 10:35Michelle Obama?

  Right.

• 10:35Speaker 02

  Little ones, yeah.

• 10:36Michelle Obama?

  So what do you do with little ones in Vegas? We used to take the girls, but we were campaigning in Vegas a lot and they loved Vegas.

• 10:44Speaker 02

  Kids love, there's a lot of fun stuff.

• 10:46Michelle Obama?

  Which I told them to stop saying out loud, you know, Malia, they're like 10 and Malia is like, we love Vegas. We love staying at the win. And I was like, you know what? Don't say that out loud.

• 10:57Craig Robinson?

  It's made to attract little kids and old ladies like our mom.

• 11:01Speaker 02

  Kids like Blackjack. They love video poker. They love, we took them to see the Michael Jackson Cirque du Soleil show. We went to see the Wizard of Oz at the Sphere.

• 11:11Craig Robinson?

  Was that great?

• 11:12Speaker 02

  Really great.

• 11:13Michelle Obama?

  How long is that gonna be there?

• 11:14Speaker 02

  I think a long time because it's doing very well. Yeah, that was fun. I took my Aunt Chippy along. She lives in Vegas, so we picked her up and brought her to the show. We went to a place called Omega Mart, which is part of this Meow Wolf.

• 11:29Michelle Obama?

  What?

• 11:29Craig Robinson?

  What's that?

• 11:30Speaker 02

  Franchise, it's these visual experiences and it's very interesting. It's really fun.

• 11:35Craig Robinson?

  Okay.

• 11:36Speaker 02

  There, I think there's one in Dallas, one in Phoenix and one in Denver or something, but it was a lot of fun. Kids loved it and they got to stay in a room, a Vegas room.

• 11:45Michelle Obama?

  A Vegas room, which in and of itself is like.

• 11:47Speaker 02

  You know, that kind of thing.

• 11:49Michelle Obama?

  Do you let them get in the minibar? Cause that can break you.

• 11:52Speaker 02

  We did not. No, you know what? I don't think they even knew the minibar was there.

• 11:56Michelle Obama?

  That's, I mean, my kids knew.

• 11:58Speaker 02

  Oh, they did, yeah.

• 11:59Michelle Obama?

  They know they knew.

• 11:59Speaker 02

  I can't even imagine.

• 12:01Craig Robinson?

  Twelve dollar candy bar.

• 12:02Speaker 02

  What my dad would have done if we'd gone even open the door of a minibar. Like when we were kids, the only vacation we ever took was, well, when we lived in Brooklyn, we would go to Hershey Park in Hershey, Pennsylvania. And then when we lived in Vegas, we would drive to LA to go to Disneyland or whatever. And it was always very stressful. The car always broke down. It was just a matter of whether we made it halfway or not. We'd be towed to California or towed back home. Those are the worst vacations. When you get towed back home.

• 12:35Speaker 02

  My dad's mad. Everyone's quiet because we don't want him to get madder, you know? But um, we would, we'd stay at motels and we had a little dog, Fluffy, and never even considered leaving Fluffy with someone. It wasn't even something that we thought of.

• 12:51Michelle Obama?

  People back then wouldn't have taken somebody's dog.

• 12:53Speaker 02

  I mean, my aunt and uncle would have. They had a dog. I don't know why we didn't, but we took Fluffy and then it was $2.50 extra to have a dog in your motel room. Of course, my dad didn't want to pay that, so we would smuggle Fluffy into the room. And then, you know, we'd be at Disneyland all day. We'd leave the dog, Fluffy and thing and we always got charged at $2.50. It was like, we never got away with it. I don't know why he went along with it.

• 13:17Michelle Obama?

  He thought, he's like, let's just see, let's just see.

• 13:19Speaker 02

  Do not disturb on the room so the maids didn't come.

• 13:22Michelle Obama?

  Don't clean.

• 13:23Craig Robinson?

  Fluffy's not gonna bark all day long.

• 13:26Michelle Obama?

  So Vegas, you were born in Brooklyn and moved to Vegas, what age?

• 13:32Speaker 02

  Nine years old.

• 13:33Michelle Obama?

  You were nine.

• 13:34Speaker 02

  So what prompted your move? I just, I just love, love to gamble and.

• 13:42Speaker 02

  What prompted our move was my Uncle Frank was a cop in New York for 20 years. And then he decided at age 40, he was going to retire from the police force. Pension was coming and he decided, I'm going to move to, we're going to move to Florida. That was their plan. They're going to move to Florida like everybody from New York does. They got to Florida, they put a small deposit on a house, a hundred dollars on like a house that was going to be built in a subdivision. They were staying with friends and in the backyard, the friends had a pool. There was an alligator in the pool in the backyard. My Aunt Chippy looked out, she goes, I didn't raise three daughters to have a meeting by a goddamn alligator.

• 14:21Michelle Obama?

  I'm with Aunt Chippy.

• 14:22Speaker 02

  And that was that for Florida.

• 14:24Michelle Obama?

  That would be it for me too. I've said this before.

• 14:27Speaker 02

  It's a reasonable fear.

• 14:29Michelle Obama?

  Anyplace where an alligator is gonna, could be in your backyard. It's like, I, I don't like mice in the house. I told Barack, you, can you imagine what I would do if I saw an alligator? I'd be like your Aunt Chippy. It's like, pick it. Everybody, we're out, we're out tonight.

• 14:47Speaker 02

  They lost the hundred dollars. They went back to Brooklyn. They made a new plan. They, my Uncle Frank had heard that if you were a police officer, you could get a job as a security guard at one of the casinos. He got a job at the Frontier in Las Vegas. And then after a year at the Frontier, which is kind of a shabby hotel, he got a job at Caesar's Palace. And because he was Italian, they almost always put the Italian guys on Frank Sinatra as part of his security detail. And I think word got out and we're like, we heard like Uncle Frank's now Frank Sinatra's bodyguard. And we had to get out there. So my grandparents were with them and we just moved to join, rejoin the family in Las Vegas.

• 15:29Michelle Obama?

  Wow.

• 15:29Speaker 02

  My Aunt Chippy's still there, 86 years old.

• 15:39Craig Robinson?

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• 16:23Craig Robinson?

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• 17:09Craig Robinson?

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• 17:51Craig Robinson?

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• 18:36Craig Robinson?

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• 18:56Craig Robinson?

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• 19:40Craig Robinson?

  You know, in my early days, as I was transitioning from my corporate job to coaching, I had a few people in my corner that made all the difference in helping me succeed. I remember working in the corporate world and trying to navigate how to climb the ranks to vice president. I had a mentor that I relied on to help me learn the rules of the game. I specifically recall asking him what it took to be a vice president. His advice still stands out in my mind today. If you want to be a vice president, act like a vice president. Those words stayed with me my whole career. Behave like the position you want,

• 20:24Craig Robinson?

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• 20:53Michelle Obama?

  What did your parents, did both your parents work? What did your dad do when he got sick?

• 20:58Speaker 02

  My mom raised us and my dad worked for a company that Howard Hughes owned called Sumo Corporation. We still don't know what it was that he did. We, I think he tried to explain it to us a couple of times and it was either too complicated or too boring. Probably both. He worked, somehow he worked in management information systems. I'm not sure what that is.

• 21:18Craig Robinson?

  I remember that. That's what they, that's they used to call IT.

• 21:22Speaker 02

  Is that right?

• 21:23Craig Robinson?

  Yes, yes.

• 21:24Speaker 02

  My dad was an IT guy?

• 21:26Michelle Obama?

  He was a, he was a genius.

• 21:29Speaker 02

  He was, he's not a genius. He, but he did like somehow run these, these systems that ran the slot machines at the casinos. And they would set the odds on the, that's as much as I know.

• 21:42Michelle Obama?

  Oh, that's plenty. That's, that's pretty good.

• 21:44Speaker 02

  And sometimes he would just clock in and go bowling and then have someone clock out for him.

• 21:48Michelle Obama?

  Did you know that for a fact?

• 21:49Speaker 02

  I found out, I found that out a couple of years ago.

• 21:53Michelle Obama?

  How many of you siblings do you have?

• 21:56Speaker 02

  I have a sister and a brother. I'm the oldest. I have sister, my sister's three years younger and my brother is nine years younger.

• 22:02Michelle Obama?

  Are you the typical oldest brother? Are you the protector? Are you the, you know, were you beaten up your, you know, your younger?

• 22:09Speaker 02

  I tortured them. Yes, yes. I beat them. I did all the things that you're supposed to do. Yeah, yeah. Psychological torture.

• 22:17Speaker 02

  But also, I'm so much older than my brother. I was kinda like a, like a brother uncle to him, really.

• 22:23Michelle Obama?

  Yeah.

• 22:23Speaker 02

  So, he was like, almost like, it was like having another parent, as far as I was concerned with him, so. But, uh, yeah, my brother works as a director and a writer. He works on South Park. He's a writer on South Park. And my sister-

• 22:40Michelle Obama?

  So you're the reason why South Park is-

• 22:42Speaker 02

  I am not the reason. My sister is a comedian, a stand-up comic.

• 22:46Michelle Obama?

  That's, that's wild. And you said she came to stand-up comedy late in life?

• 22:52Speaker 02

  Yeah, she decided about, maybe like 13 years ago, that she wanted to be a stand-up comic, and everybody was like, "What?"

• 22:59Michelle Obama?

  What did she do before that?

• 23:00Speaker 02

  She was just working in a regular jobs in an office, and decided she wanted to do it, and stuck with it, and now she does it for a living.

• 23:08Michelle Obama?

  Wow. Wow. What's her brand of humor?

• 23:13Speaker 02

  Um, observation, her life, being a mom, and things she notices, I guess. Yeah. I mean, I think that's what you'd call it.

• 23:20Michelle Obama?

  Yeah, yeah, that's, that's, yeah.

• 23:22Speaker 02

  Management information services, she does.

• 23:27Speaker 02

  But, uh, yeah, and my parents are alive, and, um, uh, full of hijinks at all times. There's always something funny going on. And, um, yeah, everybody's doing alright.

• 23:39Craig Robinson?

  And was it always that way? Like, when you were growing up, was it just like practical jokes and jokes around the table? What was it like-

• 23:45Speaker 02

  Yeah.

• 23:46Craig Robinson?

  Growing up in your house?

• 23:47Speaker 02

  A lot, very funny. Everyone's funny in our family. Literally everyone in the family's funny. The least funny person in our family would be the funniest person in most families.

• 23:56Craig Robinson?

  Yeah.

• 23:57Speaker 02

  And, yes, I started, my love of practical jokes really began with my Aunt Chippy. She is my muse when it comes to that. And I carried that into my adult life. Um, our most recent mega prank on Aunt Chippy was, we put her in a Waymo, you know, the driverless vehicle?

• 24:16Michelle Obama?

  And how old is she?

• 24:17Speaker 02

  She is, uh, she was 85 at the time, now she's 86. We put her in the car, we pretended, we had an actor playing a limo driver, and picked her up at the airport. He said, "Would you mind I have to run in and use the bathroom?" She's like, "Yeah, go ahead." Close the door, the car drives off, the limo driver.

• 24:37Speaker 02

  And um, the rest you should just watch on YouTube because it's uh, I couldn't possibly explain how funny it is.

• 24:43Craig Robinson?

  It's eighty-five, Jimmy.

• 24:45Speaker 02

  I did, you know what I did? She has three daughters, my cousins, and before, before we did this, I wrote them and I said, "Listen, I have this idea, but I'm gonna be honest with you. I don't know what's gonna happen. Like, this could potentially kill your mother. What do you think? I wanna get your permission." The three of them answered, "Yes," before I barely, I don't think I even had sent. Yeah, "Go ahead, go ahead, go ahead." So, that's how it goes in our family. No mercy.

• 25:13Michelle Obama?

  Oh my gosh, I gotta see that. That's on YouTube.

• 25:16Speaker 02

  But I started by blowing up her cigarettes. She's a um, world-class smoker. She loves Marlboro Reds. She's been smoking just like a dragon ever since I was a kid, you know? And I would get these cigarette loads. You remember those?

• 25:31Craig Robinson?

  Yeah, absolutely. We tried that on our dad when we were little.

• 25:34Michelle Obama?

  We sure did. We tried a bunch of stuff to make them stop smoking.

• 25:37Speaker 02

  To make them quit smoking. That's not why I did it.

• 25:39Craig Robinson?

  I know, I know, I got figured.

• 25:40Speaker 02

  In fact, I was like, "Please don't ever stop." But I would load them, I'd get them into her, I'd then go buy cigarettes when I was like fourteen. I'd, I'd pull the clear plastic wrapping off as carefully as I could. I'd load the whole pack of cigarettes, then seal it back up and use double-stick Scotch tape to put it back. Then I'd just leave it sitting somewhere and she'd think she got one over on me. She took the pack of cigarettes and the next day I get a call from work, "You little bastard." She'd be playing the video poker machines and just tobacco would go everywhere. Those things are the, are the best.

• 26:18Craig Robinson?

  Yeah, man. We did that to our dad and almost got in trouble.

• 26:22Michelle Obama?

  Well, did we, it was more we were dipping the tips in hot sauce.

• 26:27Craig Robinson?

  No, you, you dipped the tips in hot sauce. We, we, I put one of those exploding things in his cigarette once and it exploded. The, the beauty of the whole thing is when it explodes, the end, the tobacco goes everywhere, but you're left with a cigarette in your mouth and it's bent.

• 26:44Speaker 02

  You are absolutely right.

• 26:46Craig Robinson?

  It's bent from the explosion. It's just like a cartoon.

• 26:48Speaker 02

  If you get lucky and they take a hard drag, there will be tatters. Just, you'll just have this confetti coming out of your mouth.

• 26:59Speaker 02

  I buy them on eBay now and they still work.

• 27:02Craig Robinson?

  Still doing it.

• 27:03Speaker 02

  You can't really find them new, but you can find them all.

• 27:06Michelle Obama?

  Oh my God, yeah.

• 27:07Craig Robinson?

  And so going to school, did you get in trouble a lot at school doing stuff like that?

• 27:11Speaker 02

  A little bit, yeah, a little bit, yeah. I, you know, I was, my teachers either loved me or wanted to kill me. There was no in between really. It was either they got it and they appreciated some jokes. But I had situations in my life. Actually, when I hosted the White House Correspondents Dinner, you were there and actually we sat next to each other at that event. I told a story about my history teacher, Mr. Mills, at Clark High School in Las Vegas. George Mills was his name. He was like a big, tough, like, I think he was a Marine and a good teacher, you know, a really good teacher, was an advanced level class. But there was, he, you know, he did not, he did not like any screwing around in class.

• 27:55Speaker 02

  And finally, and I just never stopped. Finally, he said to me, he did one of the worst things anybody ever did to me. He said, here's how this is gonna go. You get, you tell one more joke and I fail you. You get an F. And, you know, I wanted to have good grades and so this was a problem, you know? And the class objected and the class spoke up in my defense, which was great, right?

• 28:19Craig Robinson?

  Yeah.

• 28:19Speaker 02

  And they said, hey, come on, whatever. He goes and he says, all right, you get one joke a week.

• 28:25Michelle Obama?

  Okay.

• 28:26Speaker 02

  Which is worse than no jokes because I'm sitting there all week. I usually wait till Friday and, you know, if it doesn't go over, it will ruin my whole week. I have to wait, you know, like, I'd be still, so I have to pick my spot and make sure I slid a good one in. And when it would happen, he'd look at, he'd turn a glare at me and I'd go, I'd just give him like, say, one joke a week, he'd be like, all right. But he did actually pull me outside the class once and he said, listen, you're a funny guy, you're a smart kid, but if you keep screwing around, you're never gonna get anywhere in life.

• 29:01Michelle Obama?

  Yeah, yeah.

• 29:02Speaker 02

  And that's how I closed my White House Correspondents Dinner speech where I said, eat it Mills, wherever you are. And in his obituary, this story is written and they asked him about, and I guess he remembered me and he thought it was a funny story.

• 29:18Michelle Obama?

  So you guess he remembered you, huh?

• 29:20Speaker 02

  Yeah, he did. He remembered me. You never know, right? I mean, there's a lot of students, but he remembered me, yeah.

• 29:26Michelle Obama?

  Wow, that's amazing. That's amazing. What do you remember most about your childhood in Vegas? I know that you had some pretty good friends and, you know, and you, you with your friends and your family, there's a loyalty. I mean, it's like, you glom onto people and they stay with you forever.

• 29:50Speaker 02

  Yeah. Is it loyalty or just no one else wants us around?

• 29:54Michelle Obama?

  No, I think it's deep love and loyalty.

• 29:56Speaker 02

  No, yeah, I have a lot of family and friends working at the show. You know, I had a great childhood. I really did. I grew up in a real middle, lower middle-class neighborhood. Most of my friends' parents were dealers or my best friend's dad was a room service butler at Caesar's Palace who worked with Sammy Davis Jr. and Bill Cosby and these, you know, these great stars of the day. And he is now in my band and his son was my bandleader.

• 30:28Michelle Obama?

  Yeah. Yeah, I, you know, I know where you are with that.

• 30:33Speaker 02

  He passed away.

• 30:34Michelle Obama?

  Yeah, yeah, yeah.

• 30:35Speaker 02

  So when, when did you say, okay, maybe I can make a living out of this stuff?

• 30:43Speaker 02

  You know, I always wanted to be an artist, like a cartoonist when I was a kid. And I never even, I didn't know anybody in show business. It wasn't like, you know, even growing up in Las Vegas, like, there was this lounge singer named Perfecto who used to come over to my Aunt Chippy's house sometimes. And that was about as close as we got to show business. Yeah.

• 31:03Speaker 02

  Perfecto, Perfecto in Motion was the name of it. And then there was another guy named Lovelace Watkins, who somehow my aunt and uncle befriended. But, um, you know, it wasn't something that, that I ever even imagined doing until I, I got on the radio, you know, that's really what, I, I read, I loved David Letterman and I read that David Letterman started in radio. And then I worked with a kid at a clothing store who said, "Hey, you're funny. You should be on the radio." He was on the college radio station. I was like, "Oh, I'd love to be on the radio." And I just kind of moved away from drawing and all that stuff that I was doing. And I got a real thrill out of being on the radio.

• 31:46Speaker 02

  I remember my first, the first time I hosted a radio show was in high school. I was on the college radio station. And they just said to me, "Yeah, we'll give you a show on Sunday night for a half hour. You find somebody and interview them." You know, it was just like this, really. And I found this guy who, I found a guest in The Yellow Pages. He was the hairstylist of the stars. And I brought him in. I wanted to know what stars hair he'd style. Turned out it was only one star. And that star was John Davidson from That's Incredible. You remember that guy?

• 32:19Michelle Obama?

  Yeah.

• 32:21Speaker 02

  We spent a full half hour talking about John Davidson's hair, which included a big white spot that was like a skunk. He had like a skunk type white spot on his hair. And it was fun and I went home and my Aunt Chippy was over the house smoking.

• 32:35Michelle Obama?

  Of course.

• 32:35Speaker 02

  She and my mother had listened, my parents had listened to it and they were so excited. And, you know, in being raised in this loud Italian family, um, just...

• 32:46Speaker 02

  Being listened to, it was a big deal. And I think that was.

• 32:50Michelle Obama?

  Getting a word in edgewise.

• 32:52Speaker 02

  Yeah, just the fact that they sat around presumably quietly and listened to me for a half an hour. Was, I just, I was so excited by it. And that's all I really wanted to do from, from there on.

• 33:05Michelle Obama?

  Wow.

• 33:06Speaker 02

  Is be a dish shocking.

• 33:07Michelle Obama?

  Did you finish college?

• 33:09Speaker 02

  I didn't know. I, I was at UNLV for a year and then my whole family moved. My dad lost his job. We moved to Phoenix. I went to Arizona State and got a job in Seattle doing morning radio before I graduated, which by the way, never would have happened.

• 33:25Michelle Obama?

  Yeah.

• 33:26Speaker 02

  I say before I graduated, as if I would have graduated. It was, that was not really. I was only going to school to avoid getting thrown out of the house. That was. My parents had no idea how much they were wasting on my education.

• 33:42Michelle Obama?

  So what was his first job in morning radio?

• 33:44Speaker 02

  It was in Seattle at a radio station called KZOK. That was my first paying job. I had a lot of jobs like calling in and doing character bits and, but none of them paid. But my first paying job was at KZOK. I did a show with my, a friend called, his name was Kent Voss. The show is called The Me and Him Show. He, he was me, I was him. And we were, we were on air every morning and we loved it. We got fired 10 months into our one year contract and then I had to move.

• 34:17Michelle Obama?

  What'd you do?

• 34:18Speaker 02

  I just, um, yeah, would you, would you blow up? I wasn't very diplomatic at the time.

• 34:24Michelle Obama?

  Uh oh.

• 34:24Speaker 02

  I was, uh, 20 and everyone at the station was, the median age was probably 45, you know? It was a classic rock station. I had never heard most of the songs that were being played, you know? Like it wasn't, it just wasn't the place I was supposed to be. And they figured that out a lot quicker than I did. And they, and they sent me back home and it was heartbreaking. It really was like one of the worst times of my life.

• 34:51Michelle Obama?

  Really?

• 34:51Speaker 02

  Yeah. Because I felt like I was on top of the world. I got this job that I wanted and I was like, we're going to live in Seattle forever. And this is going to be our town. We're going to be on the radio here. And then the next thing I knew was like, okay, um, grab your stuff from your desk. Um, and go home and don't come back. Which is weird.

• 35:09Michelle Obama?

  It's like no notice.

• 35:10Speaker 02

  Yeah. You've never been fired, obviously.

• 35:13Michelle Obama?

  I don't think I have.

• 35:15Speaker 02

  Have you been fired?

• 35:16Craig Robinson?

  I'm a coach.

• 35:17Speaker 02

  Yeah, that's part of the business.

• 35:20Craig Robinson?

  Yeah, yeah, it is an empty feeling.

• 35:23Speaker 02

  Isn't it?

• 35:23Craig Robinson?

  Yeah, even even when they owe you stuff, it's still like, oh, what am I gonna do?

• 35:37Craig Robinson?

  Does it bother anyone else that when they go on a trip, their house is just sitting there, totally unused and unwatched? I'll call up my relatives and ask, hey, anyone want to come stay at my place while I'm gone? No? No takers? Missed opportunity. That's why I love the idea of becoming a host with Airbnb. It's a great way to make sure your home is used and appreciated while you're off on that pizza tour of Chicago or whatever you've got planned. It's especially relevant because this summer, the FIFA World Cup is bringing fans from all over the world into cities across the United States. People will be traveling and looking for a place to stay while they catch the games.

• 36:21Craig Robinson?

  It's a practical way to make a little extra money while your place would otherwise be empty. If you've ever thought about hosting, this summer is a great time as we welcome FIFA World Cup fans. Your home might be worth more than you think. Find out how much at Airbnb.com/host. My kitchen has never quite felt completely put together, like it's always felt like something is missing. And then Kelly and I found these striped linen cafe curtains on Wayfair, and the effect has been perfect. Once we realized we wanted some curtains, it was just a matter of typing our ideal item into Wayfair's search bar. And of course, they have what we want plus 10 other options.

• 37:06Craig Robinson?

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• 37:49Speaker 03

  Wayfair, every style, every home.

• 37:58Speaker 02

  And how about the people? Now, that's the thing that really disappointed me more than anything. These people that you think are your friends, who you just suddenly don't ever hear from.

• 38:06Craig Robinson?

  Yeah.

• 38:07Speaker 02

  It's like you have something contagious and they don't want any part of it.

• 38:10Michelle Obama?

  It's like you used to be funny, but now.

• 38:13Speaker 02

  Yeah.

• 38:13Michelle Obama?

  You stink.

• 38:14Speaker 02

  Yeah, like it really is. And I got fired a lot of times, so it wasn't the only time.

• 38:18Craig Robinson?

  And that's what I was gonna say. You're like a coach. You get hired to get fired. How did you deal with those kinds of setbacks?

• 38:27Speaker 02

  I was always very determined. I always had a lot of confidence in myself. I felt that what we were doing was funny. I really liked my partners on the air. We felt, you know, that was nice, having a teammate. Being fired with another person is easier than being fired on your own.

• 38:45Craig Robinson?

  Yeah.

• 38:46Speaker 02

  We started a classic rock station. I went to a top 40 station from there. Then it was what they call a hot AC, which is like upbeat, adult, contemporary. Then to another top 40 station. And finally, I wound up at K-Rock in L.A., which is an alternative rock station. And that was kind of where, that was where I was supposed to be. I didn't get fired there.

• 39:07Michelle Obama?

  Yeah.

• 39:07Speaker 02

  I fit in well at that station.

• 39:09Michelle Obama?

  What do you think you were learning as you were going through this period in your life that prepared you for your ultimate shine?

• 39:19Speaker 02

  Well, I think. It was a little bit like the Karate Kids in some ways. The wax on, wax where I was like when I was at K-Rock here in LA. I was the sports guy and I wrote all the comedy bits for the show. And I did a bunch of character voices. So I did six sportscasts a morning, um, every half hour. And I wrote all the comedy bits and then I would sometimes be on the air as well. So it was just nonstop writing, write, deliver, write, deliver, write, deliver. And it just in a row. And so I learned to write, write quickly and to write and to just turn things around in a furious way.

• 40:01Michelle Obama?

  Yeah.

• 40:02Speaker 02

  Which has been great for me because I have to sit down and hash out a, you know, nine page monologue every night. And but that that learning experience, just little by little, taking on more and more and more. And having those deadlines, which is something I have to this day. It I never have writer's block because I just don't have time for it. Like I can't even, I don't even understand what it is. I I just keep going and going and going. And at the end of the night, the show's over and you're on to the next one. And there's something terrible about that. It just disappears. You can put as much work into it as you want and then it's gone. But there's also something great about it because you're constantly creating. You're constantly coming up with with stuff and that that I like.

• 40:47Craig Robinson?

  I I would love to hear Jimmy about your getting your late night gig. Like, tell, tell me about that process.

• 40:57Speaker 02

  It's a disappointing story. And it goes like this. I was, um, told that ABC wanted to meet me about a Thursday night variety show. I was hosting a show called The Man Show on Comedy Central at the time. I was also picking football games on Fox NFL Sunday. I was like their. Foot, you know, oddsmaker, or whatever you want to call it. So I was asked to come in for a meeting and I was not interested in doing. One of the weird things I did is even at my most desperate times, I would say no to things. Which turned out to be a great, I didn't, I wasn't doing it as a strategy, but it turned out to be a great strategy. Because it would, people would drive them crazy.

• 41:40Speaker 02

  And then they keep offering me things until, I did a game show called Win Ben Stein's Money. And it was like, I think the fourth thing this producer, Michael Davies, had offered me. And each time, I was just a, you know, I was the sports guy. I was making $60,000 a year, you know.

• 41:55Michelle Obama?

  Like, what are you turning down stuff for?

• 41:56Speaker 02

  The idea that I was turning down TV shows was genuinely ridiculous. And until he told me about this show, Win Ben Stein's Money, I was like, oh, that sounds funny. And he explained the premise of the game show and I was like, oh, and then it turned out to be a hit. And it led to everything else I did on TV. But I was, um, my manager's a guy named James Baby Doll Dixon. His other clients are John Stewart and Stephen Colbert, who came along later. And, um, John was going to be hired as the late night talk show host at ABC. He'd had conversations with them, they decided that they wanted to hire him. And then at the last minute, this producer, Michael Davies, who years later is now working at ABC,

• 42:40Speaker 02

  suggests to the guy Lloyd Braun, who's running the company, that he'd look at a tape from, of me. And he said, oh, the guy from the football? And he's like, yeah, yeah, he's like, oh, all right. So they looked at a tape and they were like, you know what, we're a very, this is a very blue collar network. At the time, like, according to Jim was their, like, number one show, whatever. And for whatever reason, they decided they were going to hire me. But they didn't want to tell me that's why they're interviewing me. Because I had the same manager as the guy they had already essentially offered the job to.

• 43:14Speaker 02

  So I go in under false pretenses. We spend the whole interview talking about David Letterman. Never discussed a late night talk show. I go home, I get a call the next day saying, hey, they want to hire you to, uh, to host a late night talk show. They never even offered me the job. They told me I had the job. They're like, congratulations, you're going to be hosting a late night talk show. I was like, what? I am?

• 43:43Craig Robinson?

  Okay. They knew about your strategy of saying no, so they made it so you couldn't say no.

• 43:47Speaker 02

  They knew anything about me. It was, it was a period of maybe, maybe 36 hours. And they decided to give me the job and they gave me the job. And years later, I asked Bob Iger, I was like, because I still to this day think they made a mistake. I would have, a hundred times out of a hundred, I would have hired Jon Stewart for that job. And I said to Bob, I was like, why did you? What is it that you saw in me that, you know, made you guys pick me over Jon Stewart? And he said, you were a lot cheaper. By the way, was not kidding.

• 44:22Michelle Obama?

  No, no, Bob would not kid about that.

• 44:25Speaker 02

  And that's how I wound up on the air.

• 44:27Michelle Obama?

  Right, right.

• 44:27Speaker 02

  23 years later, here I am.

• 44:29Michelle Obama?

  Just cheap, that's all.

• 44:31Speaker 02

  The discount host.

• 44:32Michelle Obama?

  That's right, that's right.

• 44:35Michelle Obama?

  What did it feel like making that transition?

• 44:37Speaker 02

  Terrifying.

• 44:38Michelle Obama?

  Really, yeah.

• 44:40Speaker 02

  Terrifying, relentless. I mean, that's, the show was live at that time.

• 44:45Michelle Obama?

  Yeah.

• 44:46Speaker 02

  And that means, and the show was on at midnight, it was on a 12:05 following Nightline. 12:05 to 1:05, which in LA time means 10:05 PM to 11:05 PM. No. Yes, no, 9:05, I'm sorry, 9:05, 10:05. So every night, I was not done with work officially until 10:30 at night. I had just gone through a divorce. I had my kids three days a week. I had my older kids three days a week by myself. I had this show five days a week. We had no structure in place. Uh, staff that 80% of them had never done anything like this before. Had no idea what they were doing.

• 45:29Speaker 02

  A host who had no idea who he was doing, what he was doing. Um, I had bunk beds in my office. So my kids, uh, could sleep. It could after school come and they'd like hang out with me. And then they'd sleep until, and I picked them up and put them in the car and drive them home. And then take them to school in the morning and start over again. And, uh, we had no guests. We had, we just really, it was a very, very difficult startup. And it went on like that for years. And then in fact, like the first six months, I, I hired all my friends, all my relatives. There was a lot riding on this, right? And I was hoping that ABC would cancel the show.

• 46:13Michelle Obama?

  It's like, please.

• 46:14Speaker 02

  I really was because then it wouldn't have been my, you know, like, well, what are you gonna do? I'm not quitting, but you know, I wasn't gonna quit, but I would have welcomed the sweet release of death at that time. And it never came. And no matter how hard I tried, it never came.

• 46:32Michelle Obama?

  Hanging on. What do you think it was that kept it going? Was it the time slot? Was it luck? Was it bad luck?

• 46:41Speaker 02

  I think it's, um, well, somehow we managed to get okay ratings, which I think is probably the number one reason that, that it stayed on the air. Because if they weren't making money that, you know, whatever.

• 46:52Michelle Obama?

  They're not doing you any favors.

• 46:54Speaker 02

  We did okay, even though the whole time they told us we were not doing okay. And we're losing money and all this kind of stuff, but. I think more than anything is I'm just bullish and um I just kept uh I had a good friend named Alex Walu who was the president of ABC at the time and he said at my 20 year anniversary, he said, you know what, you just it was just you just kept pushing that rock up the hill. This was just a this was an act of sheer willpower more than anything and it probably was it really, I just kept at it and kept doing it because I kept remembering what my life was like before it and how I would have a job for 10 months and lose it and I wanted to just I wanted to

• 47:38Speaker 02

  do everything in my power to keep it going and um if if that way if it didn't keep going, I would be okay, I would I would be able to make peace with that because you know, there's not a big there's not a huge afterlife for talk show hosts, especially back then. Now there is, now somebody like Conan is, you know, got this entirely different career.

• 48:00Michelle Obama?

  Right.

• 48:01Speaker 02

  But back then, there was you were gone, that was it, you were done.

• 48:05Michelle Obama?

  Yeah, yeah.

• 48:05Speaker 02

  Maybe you'd get a game show if you were lucky.

• 48:07Michelle Obama?

  Yeah. How were your kids in the midst of the because you have the two older kids? How were they? Because I didn't realize that you were single dadding it through it as well.

• 48:19Speaker 02

  They were at that time, my daughter was um my daughter Katie was 10 and my son was eight. My son Kem was eight.

• 48:28Michelle Obama?

  They were little.

• 48:29Speaker 02

  Yeah, they were little. They were almost exactly the age that my younger kids are now.

• 48:34Michelle Obama?

  Yeah. Do they what do they remember about that time or do they remember anything about that?

• 48:40Speaker 02

  My son Kevin works at the show now, so he's still in the bunk bed. He's 6'5", but he's still in the bunk bed. Um, they remember, you know, it's a great question. I'd like to ask them what they remember, but they kind of had the run of the place, you know, and uh and there were a lot of snacks. I'm sure that was a big thing that they remember. But we had our, you know, we had our family, our family traditions just took place at the show.

• 49:05Michelle Obama?

  Yeah.

• 49:06Speaker 02

  I'd get my son a bean and cheese burrito from Paquito Mas every, you know, like we had, my daughter would get penne marinara from the Italian restaurant across the street. We'd do the homework, you know, I'd be writing a monologue and helping them with their homework. It was just a weird mix of home and I was in a dressing room that had no windows, you know, it was like just very strange situation, but you know, what are you gonna do? That's how you, you just have to do it.

• 49:31Michelle Obama?

  Yeah, yeah, yeah. What's, what did your daughter do?

• 49:36Speaker 02

  My daughter is an artist, my oldest daughter. She, her name's Katie Kimmel. You can find her on Instagram. She's a very successful ceramics artist. She makes really clever whimsical sculptures and she has a pop-up store at The Row in downtown LA.

• 49:54Michelle Obama?

  Nice.

• 49:55Speaker 02

  And she has a baby as well, so I am a grandfather.

• 49:58Michelle Obama?

  Welcome. Ooh.

• 49:59Speaker 02

  Thank you.

• 49:59Michelle Obama?

  What do they call you? Pop-pop?

• 50:01Speaker 02

  Well, she is only eight months old, so she calls me nothing right now. And my dad is Papa, so I'm not getting that. So I, I just, I'm going with grandpa. I don't, I know it's weird, but I'm gonna hope for just grandpa.

• 50:15Craig Robinson?

  So any tips on working with family? Cause this is our first, our first go around.

• 50:19Speaker 02

  Oh, yeah. Well, I think it might be harder with you guys because you're playing the same role here.

• 50:26Michelle Obama?

  I guess that's true.

• 50:27Speaker 02

  You know, I'm in charge.

• 50:30Speaker 02

  You know?

• 50:32Speaker 02

  Although that's not great and that has, that has its downside, but I'm fortunate, and maybe it's by design, that I have, I only hire relatives who set the best possible example. For as far as working hard goes, as far as not complaining goes, as far as doing what needs to be done. Uh, they know that they have to be in the top 10% as far as that stuff goes. So, and I've been fortunate. I've had a couple of unfortunate situations. I've had to fire. My relatives, I've had this scold, my uncle. I had to call him into my office and lecture him.

• 51:14Craig Robinson?

  Yeah, that would be a joke.

• 51:16Michelle Obama?

  Ah, and then, and then how was Christmas after that?

• 51:19Speaker 02

  Well, he got over it quickly, but, uh, you know, he, my uncle Frank used to be, uh, like, he was a security guard on the show alongside Guillermo, who's my sidekick now. But Uncle Frank was my first sidekick.

• 51:32Michelle Obama?

  Mm-hmm.

• 51:33Speaker 02

  And he was the one we followed out to Las Vegas, who worked for Frank Sinatra.

• 51:37Michelle Obama?

  Oh, yeah, yeah.

• 51:37Speaker 02

  And he was a character. He was just a offbeat, funny, dense, um, man who you could pull anything over on him. And, uh, he's just, he's very hard to explain. I think the best way to explain him is he once sat in a room and had an hour-long conversation with Kermit the Frog, never acknowledging that it was a puppet. Um, talking about dating and food and places to go and things to do. And it's just an unbelievable.

• 52:10Michelle Obama?

  Is that on YouTube?

• 52:11Speaker 02

  It is, yeah, yeah. It's just unbelievable.

• 52:14Michelle Obama?

  I've got so much to do after this.

• 52:18Speaker 02

  The guy doing Kermit was like, I don't know what's going on here. Is this a joke on me?

• 52:26Michelle Obama?

  So why did he get fired?

• 52:29Speaker 02

  Oh, I didn't fire him.

• 52:30Michelle Obama?

  Oh, he wasn't, he wasn't one of the ones. Okay, oh, you had a talking to.

• 52:34Craig Robinson?

  Yeah, he got called into the office.

• 52:36Michelle Obama?

  Yes, so what did he get called, can you say, or is it a private matter?

• 52:39Speaker 02

  No, it wasn't anything bad. It was, it was just like, kind of refusing to do, like, picking and choosing what he did and did not want to do.

• 52:45Michelle Obama?

  Uh-huh, uh-huh.

• 52:46Speaker 02

  Which, you know, like, part of the fun when somebody is, uh, you know, a stooge, for lack of a better term, is you put them in situations they don't necessarily want to be in.

• 52:58Speaker 02

  And he didn't want to be in it, and then he became like a star, you know? And then he's like, I'm not gonna do that. And I'm like, uh, yeah, you are gonna do that.

• 53:06Michelle Obama?

  You were still a sto, you're a star, but you're a stooge, so.

• 53:09Speaker 02

  We need you to do all the things, not just the fun ones, yeah. So, but, uh, yeah, he was funny and he really helped get me through a lot of, uh, rocky times from a comedy standpoint, because I knew I could always turn to him and get a, he would say something crazy, you know?

• 53:40Michelle Obama?

  So when did you meet Molly?

• 53:43Speaker 02

  Molly started working at the show, I think about a year into it. And she wanted to be a writer and she became the writer's assistant. She did that for, I think, a couple of years, two, three years. And she would write jokes, you know, on the side. And I'd look at the jokes and then it just became apparent that her jokes were so strong that I needed to hire her as a writer. And I hired her as a writer and she was great. And then she became the head writer when our head writer left. And then I think it was a couple of years after that that we started dating.

• 54:16Michelle Obama?

  Yeah, Molly is everybody's favorite person.

• 54:19Craig Robinson?

  Wait, let's back up a minute. So it was a couple of years after you made her head writer that you started dating?

• 54:26Speaker 02

  Yeah.

• 54:26Craig Robinson?

  When did you start thinking she was interesting?

• 54:30Speaker 02

  Oh, you know, I know it sounds, it always sounds like phony or whatever. But when I was dating, I was dating a comedian, Sarah Silverman. It didn't, I, I'm, I don't like, I don't have that kind of brain.

• 54:42Michelle Obama?

  You're monogamous.

• 54:43Craig Robinson?

  So you had a girlfriend at the time?

• 54:44Speaker 02

  I had a girlfriend and then she had a boyfriend as well. And I also just, you know, the idea of dating somebody at work wasn't necessarily a plan I had. But when, when I broke up with my girlfriend, I just like, you know, I, I, you know, you get in that period, you're like, I'm not gonna go out, you know? It was a fairly high profile relationship, whatever. I'm just gonna hang, so I would just hang out at the show after work. We'd just hang out, a group of us. And Molly was part of that group. There were like 10 of us and we'd hang out every night. And, and then we had a lot in common and she knew it was a terrible idea for us to date and went ahead and did it anyway. I was, I was much more cavalier about the whole thing.

• 55:29Speaker 02

  I was like, it'll be fine.

• 55:30Michelle Obama?

  You're like, I'm the boss. It'll be okay.

• 55:33Speaker 02

  It'll be okay for me.

• 55:34Michelle Obama?

  That's.

• 55:35Speaker 02

  But I also went from, you know, a 13 year marriage to an eight year relationship.

• 55:44Speaker 02

  To dating Molly. So I've never been in a situation where I've been like dating.

• 55:49Michelle Obama?

  Dabbling out there.

• 55:50Speaker 02

  You know, I've never had anything like that.

• 55:53Craig Robinson?

  You weren't on the apps.

• 55:54Speaker 02

  Yeah, that's not my, yeah, we weren't even, there weren't even apps.

• 55:56Michelle Obama?

  There weren't even apps.

• 55:58Craig Robinson?

  So you, you said earlier, you, you don't know what writer's block is. You don't get writer's block. You're just used to cranking out stuff.

• 56:04Speaker 02

  Yeah.

• 56:06Craig Robinson?

  Have you ever cranked out anything where you're like, ooh, I'm nervous about doing this or?

• 56:11Speaker 02

  Oh, every day.

• 56:13Craig Robinson?

  Really?

• 56:15Speaker 02

  Yeah, but I tend to lean into those things though. If something makes me nervous, I have to be, I have to be talked out of it in a serious way. I'm always more relaxed about it. I was, and it really, that's why I was fired from all those other jobs is because I always thought, oh, they'll think this is funny.

• 56:33Michelle Obama?

  Yeah.

• 56:35Speaker 02

  I was like, oh, they'll think it's just funny. I don't think they're gonna think it's funny.

• 56:39Michelle Obama?

  It's like, you're fired.

• 56:43Speaker 02

  I'll give you an example of something terrible I did.

• 56:45Michelle Obama?

  Yes.

• 56:46Speaker 02

  This was today.

• 56:47Michelle Obama?

  Oh, okay.

• 56:48Craig Robinson?

  Fresh.

• 56:49Speaker 02

  Today is Ash Wednesday, right?

• 56:50Craig Robinson?

  Right.

• 56:51Michelle Obama?

  Oh, I forgot about that.

• 56:53Craig Robinson?

  You forgot about that?

• 56:53Michelle Obama?

  I did. Okay, anyway, because we've been in this building all day.

• 56:58Speaker 02

  So my friend, comedian John Mulaney, texted me and Stephen Colbert and said, you guys have, you guys wearing, you have ashes? Um, you know, we're all Catholic. You guys have your ashes today? And Stephen sends back a picture of, um, of himself and he's got a, it looks like, it looks like he got hit with a charcoal briquet, you know? And then I am like, kind of looking at the picture and I think, oh, this is, you know, this is funny how, what a mess this priest made on the thing. And I go into the bathroom and I get a, um, a pastel and I draw a penis on my forehead.

• 57:35Speaker 02

  And, um, I texted, I'm like, uh, I guess my priest thinks he's funny, you know?

• 57:44Speaker 02

  And I thought, oh, maybe I'll put that on Instagram.

• 57:48Speaker 02

  And, uh, yeah, no, that got, and my wife was like, no, you're not, no.

• 57:53Michelle Obama?

  Say, but if it were up to you, it'd have been thin, thin, thin.

• 57:56Speaker 02

  It left to my own devices.

• 57:58Craig Robinson?

  This is too good.

• 57:58Speaker 02

  Yeah, yeah, yeah. I probably would have done that. And now, in a way, I got, you know what? I kinda got what I needed because I did tell the story.

• 58:09Michelle Obama?

  And we're not laughing, everyone.

• 58:11Speaker 02

  I even sent it to my, um, my, my priest growing up, Father Bill Kenny. He lives in Las Vegas, Nevada. And I sent him the picture and I said, Father Bill, I, I went to church this morning and let me know if you think this is, this is appropriate, what the priest did. And then I sent him the picture of the penis on my head and he says, you need an exorcism.

• 58:37Michelle Obama?

  And you crack yourself up.

• 58:39Speaker 02

  I love, you know, my other straight man growing up, besides my Aunt Chippy, who was my, you know, who I would torture, was my priest, Father Bill.

• 58:48Michelle Obama?

  Oh, no.

• 58:49Speaker 02

  Who I've been friends with since I was a kid, you know, and, but there's no better, there's no, there's no one who can be more, who gets more, you get more shock value out of than

• 59:01Michelle Obama?

  Oh, yeah.

• 59:02Speaker 02

  the priest from your church. And he had a great sense of humor. So he always thought of it funny, but I do crazy stuff in front of the other. And even at his, it was his 50th anniversary of the priesthood and they had a big, thousands of people came to celebrate in Vegas and they called me and they said, would you speak at this? Yes, I would.

• 59:20Michelle Obama?

  I mean, that's just like.

• 59:22Speaker 02

  So I had a painting made of Father Bill, um, to celebrate the occasion. And I had it on an easel. And I had, um, you know, a sheet hanging over it. I was gonna reveal it. And, um, I gave my, you know, I talked about our relationship and I made fun of him and, yeah, it was bishops were there. And then I revealed the painting and it's a nude painting of him. Sitting on a stool.

• 59:48Speaker 02

  Covering himself in just the right spots.

• 59:55Speaker 02

  It was just great. It was really.

• 1:00:00Speaker 02

  Really like, I love when I'm doing the same things I was doing when I was 14.

• 1:00:05Craig Robinson?

  You're like, you're just a kid.

• 1:00:09Michelle Obama?

  Oh, so how does it feel that you have probably unintentionally entered into the space in comedy where you are, you know, you've become a truth teller and, you know, and there are times when, you know, you've had to go serious and even go dark. It's so completely, I shouldn't say dark, but just go real. How is that transition felt for you? Because at heart, you're a prankster, you know, you know, you, you're a morning show, radio guy, you know, but here we are in these times. And you have so bravely and

• 1:00:51Michelle Obama?

  boldly used your platform to speak truth to power, as they would say.

• 1:00:58Speaker 02

  Well, thank you. I don't think of it as bravely, boldly, maybe would be a good description, but to me, it just seems obvious and unavoidable. And I, I don't see that, I just can't imagine on those nights, talking about anything other than what we are talking about. And, and I give a lot of credit to my colleagues for doing the same thing. I think it would be embarrassing if we didn't talk about this stuff. It would be shameful. Not that I think everyone has a responsibility to speak out whatever, if you're comfortable doing that. But, you know, my job, I've always said, since the very beginning, even when

• 1:01:43Speaker 02

  I was on the radio, is to talk about what is going on in people's lives and what is going on in, you know, if you're doing local radio in your town, and if you're doing a national television show in your country. And these are things that I, I take very seriously. And of course, you know, I like to, I love telling jokes. I love being funny. I love when the audience laughs. There's nothing that's more exciting to me than that. But well-rounded human beings don't behave that way. And to say that, well, your job is this, it makes me, I bristle at that. Because first of all, don't tell me what

• 1:02:24Speaker 02

  my job is. You know, I don't tell you what your job is. My job is whatever I decide my job is, whatever my employer allows me to do. That's what my job is. And

• 1:02:37Speaker 02

  Comedians have been doing this for a long time.

• 1:02:40Michelle Obama?

  So true.

• 1:02:40Speaker 02

  And, you know, from my generation, George Carlin, Richard Pryor. It just shows a great deal of ignorance when it comes to comedy to say, well, Johnny Carson didn't do this. Like, well, first of all, we're living in a different time. And secondly, how do you know Johnny Carson wouldn't do it? I bet Johnny Carson would talk about it. I bet Johnny Carson would be absolutely mortified by what's going on.

• 1:03:06Michelle Obama?

  Mm-hmm.

• 1:03:06Speaker 02

  And I do think that he would probably have a greater impact than than any of us do. But, um, uh, I, you know, I don't, I don't love those nights. It's not, I feel uncomfortable. I get emotional. I, I, I lose control sometimes of my emotions, which is embarrassing to me. But I just feel like I wrestle with myself throughout the day and I go, am I gonna talk about this? Am I gonna talk about this? Am I gonna talk about this? And then I just go, yeah, of course, you have to talk about this. You might not want to, but you have to. And that's it.

• 1:03:44Michelle Obama?

  Yeah, yeah.

• 1:03:45Speaker 02

  Um, I wish we didn't have to do it.

• 1:03:47Michelle Obama?

  I know.

• 1:03:47Speaker 02

  I hope there's a day that we, we don't anymore. We can just go back to fun.

• 1:03:51Michelle Obama?

  It would be nice. It would be nice.

• 1:03:53Craig Robinson?

  Do you, do you worry that comedians will censor themselves in this environment?

• 1:04:02Speaker 02

  I think, I think it, what worries me most is when comedians warp their sensibilities for whatever reason. Um, do people censor themselves? I don't know. I don't, uh, do, do television networks censor themselves? Absolutely. Have they always censored themselves? Yes, but for different reasons. Um, I was listening to you guys talk to Henry Winkler and, um, ABC wouldn't let him wear his leather jacket unless he was riding a motorcycle.

• 1:04:34Michelle Obama?

  That's right, yeah.

• 1:04:36Speaker 02

  I mean, how quaint is that, you know? Like leather jackets or some kind of, like.

• 1:04:41Michelle Obama?

  It's like, it's the devil.

• 1:04:44Speaker 02

  Entryway to gang membership.

• 1:04:45Michelle Obama?

  If you look at it, you'll go blind.

• 1:04:48Speaker 02

  But I do think that there are people who are pretending to be something other than what they are in search of an audience. And it's especially sad to me. It's especially sad to me because you look at, you know, you look at some of these comics and, you know, maybe they're not doing so great and they, you know, I'm gonna pick up this MAGA torch and maybe people will support me just because of that.

• 1:05:20Michelle Obama?

  Well, it's important for people to know that for some of these folks, this is a game. This is a hustle, you know?

• 1:05:29Speaker 02

  More than, more than, more than not, I would bet.

• 1:05:32Michelle Obama?

  Because there's a lot, you know, we saw it in the White House, you know, especially around the holidays when there would be a set of people who would demonize my husband on TV and then be in line for a picture with their grandchildren, you know, essentially saying, "My granddaughter loves you." And, you know, and it's like, if you believe the things that you believe, if I believed this about someone, I wouldn't be in the line. I wouldn't be in the house, you know? So there's a lot of wink and a nodding that goes on. It's like, you know, and I think that is, does a disservice to the people who are following people.

• 1:06:11Michelle Obama?

  It's like, oh, how, how much do you believe in this, you know, stuff you're spewing? Because if you don't believe it, don't play with people's lives like that.

• 1:06:25Speaker 02

  Yeah, it's, it's hard to, it's on some, some levels, it's hard to understand and others, it's easy to understand because when it comes to how people make their money, they seem willing to compromise in a lot of ways. And I think I get.

• 1:06:44Speaker 02

  A little more backlash than someone who maybe like, like Jon Stewart, who kind of came out of the, the shoot of very outspoken liberal. Because I didn't talk about politics and because it wasn't really part of my act. It wasn't really something I, I, I wasn't particularly interested in.

• 1:07:04Michelle Obama?

  You were putting bombs in cigarettes and sending.

• 1:07:08Speaker 02

  I was mostly, I was.

• 1:07:09Michelle Obama?

  With the.

• 1:07:10Speaker 02

  Doing sports jokes and this kind of stuff. And I, I'm hosting the man show, you know, which people like, were like, wow, you've betrayed us. Like, no, I've never, I've, I've always been like this. I, you know, I've, my parents are, you know, of course, you know, that's how it starts. Whatever your parents are, usually that's what you are, you know? And my parents are very liberal people, you know, very, very, very liberal people. And I always have been, uh, you know, I've, I've never voted for a Republican in my life. Uh, just always been of this mindset. And I think people were like, just shocked to hear it because you assume somebody you like is, thinks like you. And I don't mind if people think differently.

• 1:07:52Speaker 02

  I have, I have some very close friends who, who think very differently. And I'm okay with that. I, I, I understand that people have different life experiences and believe things. I know, I personally believed certain things to be true for a long time in my life and realized that they weren't.

• 1:08:13Michelle Obama?

  Yeah.

• 1:08:13Speaker 02

  And just, you have to allow for that. And lately, uh, you know, I posted something on Instagram about some of these, um, primarily podcasters who now are having second thoughts about, um, who they endorsed for president. And I, I'm grateful to them for being honest and admitting that they were mistaken.

• 1:08:36Michelle Obama?

  Absolutely.

• 1:08:37Speaker 02

  It happens almost never.

• 1:08:39Michelle Obama?

  Right, right. That people admit when they're wrong.

• 1:08:41Speaker 02

  It's the cardinal rule of MAGA is to never admit when you are wrong. And I can't think, first of all, it's the opposite of Christianity. I mean, it's the, the basis of the whole faith, you know, is asking for forgiveness. And, um, that seems to be. Cast aside, but I welcome those people. I am, I, I, I don't think there's any way forward if we don't.

• 1:09:05Michelle Obama?

  Right.

• 1:09:05Speaker 02

  That's what I think. And I've heard people that I have a great deal of respect for, who, with whom I'm on the same page, whatever you want to say, who go, oh, no, they must, you know, they must be punished for their sins. I disagree.

• 1:09:19Michelle Obama?

  Yeah.

• 1:09:19Craig Robinson?

  What makes you excited about the future of comedy?

• 1:09:23Speaker 02

  Um, I love the niche aspect, aspect to comedy now, where you can, like, our announcer on our show, Lou, Lou Wilson, he does a show that's very popular on the internet about Dungeons and Dragons. And it's like a funny internet show about Dungeons and Dragons. And he can do it and he can get an audience and he makes money from it. And it's amazing to me because even, you know, when I was coming up in order, you had to first get on the radio, which is like, basically, you, how do you get on the radio if you're not on the radio? You just have to hang around, you just have to annoy them until they put you on a little bit.

• 1:10:08Speaker 02

  And then they put you on a little more and then hopefully you get better. But now you can open up your computer, you could do a whole show for, you know, your friends or for nobody, whatever. And then if it's good, usually it catches on. And I think that's a lot of fun. And a lot of people see that as like, um, the end of, of comedy as a business, but I think it's great. I mean, I think you'll see a lot more people doing it. Um, maybe not for as much money, but you'd be able to, if you're good, you can make a living and really only talk about what you want to talk about.

• 1:10:43Michelle Obama?

  And there are so many funny people out there. I mean, it's like, you know, I'm, yeah, I get funny things sent to me because I try not to be on social media a lot. But I could spend the day just cracking up about people.

• 1:10:57Speaker 02

  I love that too. Like, you know that when you get a video that's funny and it's somebody you've never seen before, that thousands of other people are also sending. That video around and that's just something. It's one of the few good things I think about social media that, you know, we forget, I think, sometimes that there are also good things. And it is one of the good things is that exposure and just even those reps you get as, you know, when you're 15, you get to be on, you get to do a show every day. I think like in 40 years, we're gonna have like some incredibly developed talents that are very unique and very unusual.

• 1:11:37Speaker 02

  And I like that.

• 1:11:38Craig Robinson?

  Who are some of the younger guys that you see coming along? That excite you? Can you say without?

• 1:11:46Speaker 02

  Without like thinking too hard, you know, that's, that's always, I always get nervous because, because I, I will go home and go, ah.

• 1:11:53Michelle Obama?

  I forgot about him.

• 1:11:54Craig Robinson?

  He's gonna kill me.

• 1:11:57Speaker 02

  We had a comic named May Martin on the show last week, who was very, very funny.

• 1:12:05Speaker 02

  And that's one of the great things about my, my job is sometimes I can see people. Uh, and I can put them on television if I want to, you know?

• 1:12:15Michelle Obama?

  But we've got a listener question, too.

• 1:12:17Craig Robinson?

  We do, we always have a listener question that we can offer some advice to some, one of our listeners.

• 1:12:25Speaker 04

  Hi, my name is Andrea. I'm a mom of three-year-old twin girls and their one-year-old baby brother. And I have a full-time job while my husband stays at home with the kids. He has the harder job by a thousand miles. I have a drive to be with my kids through their various phases, but being the sole breadwinner, I'm really only present on weekends and at bedtime. I know people, including you, say this time goes so quickly, so savor every moment. I also know that you raised your kids during what was probably the most stressful and public-facing period of your lives. All that to say, I try to stay present and I'm also trying to parent myself first to show a good example to the kids when I am there. Can you give me a little guidance on prioritizing when to stay present,

• 1:13:08Speaker 04

  what to be there for, and what I shouldn't worry so much about? So that my kids feel like their mom is both their foundation and a successful person to emulate? I want to be focused on the parts of parenthood that my kids can reflect on positively once they're out in the world, being their spicy selves. Thanks, and I love your vibe.

• 1:13:29Speaker 02

  Well, number one, I would, Andrea, um, your husband comes first, no matter what.

• 1:13:38Speaker 02

  Oh, sorry, I'm talking to Molly.

• 1:13:39Speaker 04

  We weren't, we weren't ready for that one.

• 1:13:44Speaker 02

  Well, that's a tough one, especially for women, because, you know, there's, you know, these presumptions that you, like, I guarantee you, if the roles were reversed there, it'd be like, wow, what a great dad he is. He wouldn't be writing, he wouldn't be writing in like, how can I be more present? He'd be like, I'm with these kids all weekend. And sometimes at night.

• 1:14:11Speaker 02

  But it does seem like, like, we're now, as adults, expected to, I know we still have 24 hours in the day. Now, I'm just comparing, as we all do, to what our parents did, right? There's still only 24 hours in the day. And now, we're expected to do so many more things. And I don't know why that is. I don't know if it's, if we've learned that we need to, or if it's pressure that we feel from others. I don't know what advice I would give, other than, you're doing your best, just do your best. I mean, and that has to be enough, because you have to be at work all day, every day. And even just to, hopefully, the dad's doing

• 1:14:56Speaker 02

  a good job, right? And if he's doing a good job, which I don't know, it sounded like she thinks he's doing a good job.

• 1:15:01Michelle Obama?

  Yeah, she wasn't complaining. Who would have heard about it?

• 1:15:03Speaker 02

  Let him do his job. You do your job, and then you do as much of the job together as you can. And release that, that guilt. My wife, this, I, we have this conversation too. She's like, I feel like I'm not, you know, I'm not doing, I, I, I'm not doing enough at work, I'm not doing enough for the kids, I'm not doing enough at home. And, you know, of course, I'm always full of wisdom.

• 1:15:29Speaker 02

  She says this the other day, I'm like, what do I, all I think of is, what can I say to get out of this room, um, without causing a incident?

• 1:15:40Speaker 02

  And what I did was, I, um... I touched her on the face and I said, you're doing a great job. You're doing, you're doing everything you can and that's all you can do.

• 1:15:49Michelle Obama?

  Yeah.

• 1:15:49Speaker 02

  And I walked right out of the room. And I was so pleased with myself. Yeah, I mean, even just like me recounting this, I'm feeling a surge of pride in the way I handle it like you would in a movie.

• 1:15:59Michelle Obama?

  You were. And seen.

• 1:16:03Speaker 02

  And there he goes, off to work.

• 1:16:05Michelle Obama?

  What a great man.

• 1:16:08Michelle Obama?

  What a great man.

• 1:16:10Speaker 02

  But it's hard, right?

• 1:16:12Michelle Obama?

  Yeah, yeah.

• 1:16:13Speaker 02

  It is.

• 1:16:13Michelle Obama?

  But I do think you're right, Jimmy. I mean, the one thing I would say to Andrea is really try not to parent from guilt. Because I think that's more damaging than how much time you are or are not spending. Like if you try to replace your time with the wrong things, like being more lenient. Or, you know, always being the fun parent. Or, you know, if your, if your guilt is preventing you from creating the kind of boundaries and all of that. That, to me, is the thing that winds up hurting kids is that they're raised by a mother that feels guilty. So they, they learn to play on that guilt.

• 1:16:55Michelle Obama?

  And that may not be, that, that is not the best thing for them. So I learned that my kids react to the schedule the way I react to it, the way Barack reacts to it. Right? We learned that in the White House. So we started going, okay, yeah, will you live in the White House? It's really no big deal. It's just, this isn't about you. Just go to school. Yes, you have security, but you know, that's just the state of life. You're fine, you know? This isn't about you. What your dad does isn't about you. And all you have to do is take care of your business, you know? And I found that with them having their, their regular routine and their lives.

• 1:17:36Michelle Obama?

  On track, the older they get, that's, that's really what they care about. You know, but if there's something that they can count on, like this is the time I have with my mom. And it's good time, you know, so that you're not, so that she's not using the guilt, the time just being guilty, that she's still showing up her full self for the time that she has.

• 1:17:59Speaker 02

  This is so much better than my advice to Andrea.

• 1:18:03Speaker 02

  Yesterday, we were at lunch and this place has a gift shop as well. And so we're waiting for the food and I'm sitting with my daughter Jane. And um, my wife is in the gift shop with Billy. And Jane goes into the gift shop and they come back and they're having a negotiation. Jane wants a jelly cat. These are these stuffed animals that are very popular and they make different ones. And she's like, Mom, I just want, and Molly said, well, um, you know, you should, your birthday's in July. And you should put that on, on your birthday list then if you want it. Um, but we're not buying a jelly cat right now. And they go back and she, and she, and my daughter's relentless, you know, she's going on and she's like,

• 1:18:49Speaker 02

  but I did this and that. And so no, Jane, I said, no, you know, whatever. And I'm sitting there and watching the whole thing. And finally I go, I'll buy it for you.

• 1:18:57Michelle Obama?

  Oh, Jimmy.

• 1:18:59Speaker 02

  And I just, and they both started cracking.

• 1:19:03Speaker 02

  I just said, I'm just gonna be the worst parent imaginable.

• 1:19:07Michelle Obama?

  Well, I'm gonna end this jelly cat issue. It's yours.

• 1:19:11Speaker 02

  I'll buy it for you.

• 1:19:12Michelle Obama?

  Here's two.

• 1:19:15Speaker 02

  And it was, it was such an antisocial act that.

• 1:19:21Speaker 02

  But I did buy it for her ultimately and um, and no lessons were learned.

• 1:19:25Michelle Obama?

  Yeah, and none whatsoever. You just screwed Molly. That's all you did.

• 1:19:31Speaker 02

  So brazenly though, that I felt it was okay.

• 1:19:34Michelle Obama?

  Totally ran over, you backed over Molly and then drove back over her.

• 1:19:40Michelle Obama?

  Oh my goodness.

• 1:19:42Speaker 02

  Good luck Andrea.

• 1:19:43Michelle Obama?

  Yeah, yeah, you're gonna be fine. You're gonna be fine. Well, this has been great.

• 1:19:50Speaker 02

  Yeah, it was a lot of fun.

• 1:19:52Michelle Obama?

  Yeah, what's next on the Jimmy Kimmel train?

• 1:19:55Speaker 02

  Let's see. Um, I have an appointment with my ENT on Friday.

• 1:20:03Speaker 02

  Is that interesting?

• 1:20:07Speaker 02

  Nothing, you know, we're off for the rest of the week. I will rest up and then go right back at it.

• 1:20:11Michelle Obama?

  Go right back at it.

• 1:20:12Speaker 02

  Right back into the mess.

• 1:20:13Michelle Obama?

  Yeah.

• 1:20:14Speaker 02

  And it is a mess.

• 1:20:15Michelle Obama?

  It's a, it's a mess, but you handle it beautifully.

• 1:20:18Speaker 02

  Oh, thank you.

• 1:20:19Michelle Obama?

  You really do.

• 1:20:21Speaker 02

  I finally handled something beautifully in my life.

• 1:20:24Michelle Obama?

  Yeah, well, you, you've got this one down. Yeah, it's fun. It's fun watching you. Yeah, yeah. And thank you for gracing us, you know.

• 1:20:32Speaker 02

  Oh, yeah.

• 1:20:33Michelle Obama?

  Finally, how did it feel being on the other side of the interview chair?

• 1:20:37Speaker 02

  It's fun, actually. You know, I like talking to you guys. You're, you're, I like, love the brother sister dynamic. I could probably ask you 10,000 questions about that just to start with.

• 1:20:47Michelle Obama?

  One day we'll both be on your show.

• 1:20:49Speaker 02

  Yeah, that would be fun.

• 1:20:50Michelle Obama?

  That would be funny.

• 1:20:51Speaker 02

  Maybe on like National Siblings Day or something like that.

• 1:20:54Michelle Obama?

  That's right. And we could play a joke on Craig.

• 1:20:57Speaker 02

  Oh, well, will you?

• 1:20:59Michelle Obama?

  Shh. But he'll forget about it by the time we do.

• 1:21:02Speaker 02

  Or we could just do something, you could just both do something to Aunt Chippie.

• 1:21:05Michelle Obama?

  Oh, that's great. Oh, my God, no, no. No, because I do not want to be responsible for any kind of accident. It's like, I don't know.

• 1:21:14Speaker 02

  Listen, I'm gonna kill her eventually. Might as well go out with, you know, an A level.

• 1:21:24Michelle Obama?

  Oh, Jimmy, thank you so much for everything you're doing. We love you, love you so much.

• 1:21:30Speaker 02

  Thank you, guys, thanks.

• 1:21:53Speaker 05

  Hi, I'm Molly Graham, host of Work Life, a podcast from TED. The most important lessons about work usually aren't the ones anyone teaches you. They come from experience, from uncertainty, from figuring things out as you go. On this show, my expert guests and I explore how careers really unfold. Through change, through doubt, through the decisions that shape who we become over time. Because those moments aren't the exception, they are the work. Listen to Work Life wherever you get your podcasts.