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Jimmy Kimmel
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.
Malia Obama
That's just like.
Jimmy Kimmel
So I had a painting made of Father Bill to celebrate the occasion, and I had it on an easel, and I had a sheet hanging over it. I was gonna 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. Oh, my. Sitting on a stool.
Malia Obama
This episode is brought to you by Shipt and Chase. Home Lending.
Craig Robinson
Hey, Mish.
Malia Obama
Hi, Craig. Good.
Craig Robinson
How are you?
Malia Obama
That's a good jacket. Have you worn that before?
Craig Robinson
I wore this to the Christmas party. I haven't worn it on an episode yet.
Malia Obama
That's cool. Yeah, it's cool on all fronts. The color is good. It feels smooth. Now, can you get that in other colors?
Craig Robinson
Yes, I have this in a different. I have a couple of these. Yes, go on.
Malia Obama
I'll break them out later on.
Jimmy Kimmel
Yeah.
Malia Obama
Fly boy. Fly boy. So what's new and exciting for Craig Robinson Land?
Craig Robinson
Not much. No, not much.
Malia Obama
Man, you're boring.
Craig Robinson
You know, I will say so. This trip to LA has been great. Now the sun's back out, but I've been cramped up. Cooped up, Cooped up. 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 easy.
Malia Obama
We were just talking about how many Airbnbs do you think you've stayed in since we launched, imo, because you get around.
Craig Robinson
I do. And so I tried to figure it out. We've done 40 episodes, but you don't do one per episode. So you figure, on average, we've done four or five.
Malia Obama
How many total tapings have we done in the last year, team?
Craig Robinson
And I'd say about ten tapings.
Malia Obama
Separate tapings.
Craig Robinson
Because once we started doing this, then I was just in my own personal life. I was doing Airbnb stuff.
Malia Obama
Airbnbs for all your travel, your trips, the things with the boys.
Craig Robinson
The boys, all of that stuff. So I would say since last August. So a year ago. August, probably 2025.
Malia Obama
But it has been a great year one, 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 them. But he just so happened you've been using janky a lot. I really 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. So I'm speaking of janky.
Craig Robinson
No, that's not right.
Malia Obama
Our guest this episode.
Craig Robinson
We are very excited about our next guest and 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.
Malia Obama
Uh huh.
Craig Robinson
That's never happened, right?
Malia Obama
No, because no one invites you.
Craig Robinson
Nobody invites me anywhere. Jimmy invited, 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.
Malia Obama
She thought it was the other Craig Robinson.
Craig Robinson
I don't know what she thought, but
Malia Obama
I was like, how do you forget that? How do you confuse that?
Craig Robinson
Who would forget being on Jimmy Kimmel's show? I mean, the green room aspect of his show, the music, I mean, it's
Malia Obama
a good green room.
Craig Robinson
It was a real memorable vibe, as my kids would say. It was a vibe. It was drinks and food and music.
Malia Obama
Strippers. No, no, there weren't strippers. That was only with me. Right, Jimmy, the male strippers. I didn't tell Barack, but we were,
Craig Robinson
you know, and I'm sure Jimmy wouldn't have remembered if I was on. He would remember if you were on. So we were doing some. So Crystal was doing some research and found out right before we came on
Malia Obama
that you were right. I was, yeah. I would like to thank you for.
Craig Robinson
To get home.
Malia Obama
Right. And tell Kelly. Well, let's properly introduce Jimmy Kimmel.
Craig Robinson
Yes, let's do that. Jimmy Kimmel serves as host and executive producer of Jimmy Kimmel Live,
Jimmy Kimmel
which has
Craig Robinson
become 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.
Malia Obama
Oh, he's just hot because he's got those cute jeans on.
Craig Robinson
Welcome, Jimmy.
Jimmy Kimmel
Come on in.
Malia Obama
Hi Jimmy. See, look. Look how cute his jeans are. How are you?
Jimmy Kimmel
Good. I'M cute.
Craig Robinson
I'm. Good to see you, man.
Jimmy Kimmel
How are you?
Malia Obama
Turnabout. Fair play. Look, looky here.
Jimmy Kimmel
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.
Malia Obama
Did you see she. Did she really?
Craig Robinson
Where is she? Why did she do. Why didn't she come?
Jimmy Kimmel
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.
Craig Robinson
Did you have striped jeans on?
Jimmy Kimmel
I very much remember you being on the show. I remember it quite well. I remember we talked about coaching. We talked. 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.
Craig Robinson
Thank you. Thank you for saying that. The weird.
Jimmy Kimmel
The thing that you might want to be concerned about is the fact that she doesn't remember.
Craig Robinson
I know.
Malia Obama
That's the thing. And Kelly, his wife remembers everything, so maybe.
Jimmy Kimmel
Except me.
Malia Obama
No, maybe she didn't remember him.
Craig Robinson
Well, you know what it was?
Malia Obama
What?
Craig Robinson
That was one of the shows where I came alone. Usually she would come. Come with me, but I think I flew down. I was in Oregon at the time, so I flew down.
Jimmy Kimmel
It may have been a blind spot caused by jealous rage.
Malia Obama
That's right.
Jimmy Kimmel
That's right.
Craig Robinson
There you go.
Jimmy Kimmel
Gotcha.
Malia Obama
We were asking. So you're not sure when this is going to air, but right now, you guys are on a weak hiatus.
Jimmy Kimmel
We're on break. Yeah.
Craig Robinson
Right now?
Malia Obama
Yeah. Yeah. How does that work? I mean, it feels like this talk show thing is pretty grueling.
Jimmy Kimmel
It is.
Malia Obama
It's just like.
Jimmy Kimmel
It's grueling.
Malia Obama
So what's the week break feel like? Are you, like, chilling? Are you.
Jimmy Kimmel
It feels brief. You know, we did actually, we rented an Airbnb in Phoenix.
Malia Obama
Really?
Jimmy Kimmel
We rented. We went to visit our friends there. I have a friend named Chris Bianco. He's a great pizza chef, I think. You had his pizza?
Malia Obama
Oh, yeah, absolutely.
Jimmy Kimmel
And we rented a beautiful house. He brought his kids over. 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.
Malia Obama
Aw.
Jimmy Kimmel
He. It took four years again. He's had it for six weeks. We're about to get in the car to go to his pizza place. He accidentally stepped on the. 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.
Malia Obama
Oh, my gosh.
Jimmy Kimmel
They were very nice about it, though. No problem.
Malia Obama
Did he. Did he trash the car?
Jimmy Kimmel
The car is trashed. Our rental car was trashed. It was a. It was like a video game type scenario.
Malia Obama
He was so excited.
Jimmy Kimmel
Yeah, he was. It was sad. It was sad.
Malia Obama
It is so sad.
Jimmy Kimmel
But I told him, don't. We're gonna look back and laugh at this.
Craig Robinson
So tell me this. Did it have the old fashioned gear shift that was on the side where you had to.
Jimmy Kimmel
No, it had the. It was down. I know this because I drove it shortly before he drove it into the house.
Malia Obama
And it's so good.
Jimmy Kimmel
And I remember thinking, this car's too fast. It's like, it's too responsive. You know, it's a little bit dangero.
Craig Robinson
Yeah.
Malia Obama
But it has to be in the right gear.
Jimmy Kimmel
It does. That's one of the things that we learned.
Craig Robinson
Yeah. So if you're in. If you're in drive and should be in reverse, it just doesn't work.
Malia Obama
So when that happens to your friend, are you laughing at him? Are you sort of like, aw, buddy,
Jimmy Kimmel
you know, I felt bad for him. I did. I mean, it's, you know, 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.
Malia Obama
You held it.
Jimmy Kimmel
I held it.
Malia Obama
We are laughing now.
Jimmy Kimmel
He's probably still not laughing, but, you
Malia Obama
know, maybe by the time this airs.
Jimmy Kimmel
Maybe doubtful, but maybe, yeah.
Malia Obama
Were the kids in the car?
Jimmy Kimmel
The kids were in one. 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.
Malia Obama
So did you get pizza at least?
Jimmy Kimmel
We did go. We did go for pizza afterwards because
Malia Obama
the kids were like, are we still. Because kids don't care. They're like, well, we thought we were getting pizza.
Jimmy Kimmel
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. We just left.
Craig Robinson
Oh, man.
Malia Obama
That's what you do on your break. Yeah. No wonder it didn't feel long.
Jimmy Kimmel
You were in the crisis.
Malia Obama
Yeah.
Jimmy Kimmel
We took the kids to Vegas. We had a lot of fun in Vegas.
Malia Obama
So your kid, the little Ones, Yeah. Right?
Jimmy Kimmel
Little ones, yeah.
Malia 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.
Jimmy Kimmel
Kids love. There's a lot of fun stuff, which
Malia Obama
I told them to stop saying out loud. You know, Malia, they're like 10. And Malia's like, we love Vegas. We love staying at the Wynn. And I was like, you know what? Don't say that out loud.
Craig Robinson
But it's made to attract little kids and old ladies like our mom.
Jimmy Kimmel
Kids like blackjack? They love video poker. No, 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.
Craig Robinson
Wasn't that great?
Jimmy Kimmel
Really great.
Craig Robinson
How long is that going? Did they like it?
Jimmy Kimmel
I think a long time because it's doing very well. Yeah, that was fun. 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 what? Franchise. It's these visual experiences, and it's very interesting. It's really fun. I think there's one in Dallas and 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. It looks like Liberace died in it. You know, that kind of thing.
Malia Obama
Do you let them get in the minibar? Because that can break you.
Jimmy Kimmel
We did not. No. You know what? I don't think they even knew the mini bar was there.
Malia Obama
My kids knew.
Jimmy Kimmel
Oh, they did?
Malia Obama
Yeah, they knew.
Craig Robinson
I can't even imagine $12 candy bar
Jimmy Kimmel
that my dad would have done if we'd gone even open the door of a mini bar. When we were kids, the only vacation we ever took was 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, everybody's on. My dad's mad. Everyone's quiet because we don't want him to get madder, you know? But we wouldn't. 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 would.
Malia Obama
And people back then wouldn't have taken somebody's dog.
Jimmy Kimmel
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. And 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 thinking we always got charged at 250, it was like we never got away with it. I don't know why he went along with it exactly.
Malia Obama
Thought he's like, let's just see.
Jimmy Kimmel
He put the do not disturb on the room so the maids didn't come.
Malia Obama
Don't clean.
Craig Robinson
Fluffy's not gonna bark all day long.
Malia Obama
So Vegas, you were born in Brooklyn and moved to Vegas, what age?
Jimmy Kimmel
Nine years old.
Malia Obama
You were nine.
Craig Robinson
So what prompted your move?
Jimmy Kimmel
I just loved. Love to gamble. And 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 gonna retire from 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, $100 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.
Malia Obama
I'm with Aunt Chicken.
Jimmy Kimmel
And that was that for Florida.
Malia Obama
That would be it for me, too. I've said this before. Alligator.
Jimmy Kimmel
It's a reasonable fear.
Malia Obama
Any place where an alligator is gonna could be in your backyard. It's like, I don't like mice in the house. I told Barack, 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.
Jimmy Kimmel
They lost $100. They went back to Brooklyn. They made a new plan. 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.
Craig Robinson
Wow.
Jimmy Kimmel
My aunt chippy's still there. 86 years old.
Craig Robinson
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Malia Obama
What did your parents did your did both your parents work? What did your dad do when he.
Jimmy Kimmel
My mom raised us and my dad worked for a company that Howard Hughes owned called Summa Corporation. We still don't know what it was that he did. 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.
Craig Robinson
Yes, I remember that. That's what they. That's they used to call it.
Jimmy Kimmel
Is that right?
Craig Robinson
Yes. Yes.
Jimmy Kimmel
My dad Was an IT guy.
Malia Obama
He was a. He was a genius.
Jimmy Kimmel
He's not a genius, but he did, like, somehow run 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.
Malia Obama
Oh, that's plenty. That's. That's pretty good.
Jimmy Kimmel
And sometimes he would just clock in and go bowling and then have someone clock out for him.
Malia Obama
Did you know that for a fact?
Jimmy Kimmel
I found out. I found that out a couple of years ago.
Malia Obama
Oh, God. How many of you siblings do you have?
Jimmy Kimmel
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.
Malia Obama
Are you the typical oldest brother? Are you the protector? Are you the. You know, were you beating up your. You know.
Jimmy Kimmel
I tortured them. Yes. Yes, I beat them. I did all the things that you're supposed to do. Yeah, yeah. Psychological torture. But also, I'm so much older than my brother. I was kind of like a like, brother uncle to him. Really?
Malia Obama
Yeah.
Jimmy Kimmel
So he was like. Almost like. It was like having another parent as far as I was concerned with him. So. But 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.
Malia Obama
Oh, so you're the reason why south park is.
Jimmy Kimmel
I am not in the dinner. My sister is a comedian, a standup comic.
Malia Obama
That's wild. And you said she came to stand up comedy late in life.
Jimmy Kimmel
Yeah. She decided about maybe like 13 years ago that she wanted to be a standup comic. And everybody was like, what.
Malia Obama
What did she do before that?
Jimmy Kimmel
She was just working in regular jobs in an office and decided she wanted to do it, stuck with it, and now she does it for a living.
Malia Obama
Wow. Wow, what. What's her brand of humor?
Jimmy Kimmel
Observation, her life, being a mom and things she notices? I guess. Yeah. I mean, I think that's what you'd call it.
Malia Obama
Yeah. Yeah, that's. That's. Yeah.
Jimmy Kimmel
Management Information Services. She does. But, yeah. And my parents are alive and full of hijinks at all times. There's always something funny going on. And, yeah, everybody's doing all right.
Craig 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 growing up in your house?
Jimmy Kimmel
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.
Malia Obama
Yeah.
Jimmy Kimmel
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 carry that into my adult life. Our most recent mega prank on Aunt Chippy was we put her in a waymo. You know, the driver of this vehicle.
Malia Obama
And how old is she?
Jimmy Kimmel
She is. 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. Limo driver. And the rest you should just watch on YouTube because it's. I couldn't possibly explain how funny it is.
Craig Robinson
85, Jimmy.
Jimmy Kimmel
I did. You know what I did? She has three daughters, my cousins.
Malia Obama
And
Jimmy Kimmel
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 even. I don't think I even hit send. Yeah, go ahead, go ahead, go ahead. So that's how it goes in our family. No mercy.
Malia Obama
Gosh, I gotta see that. That's on YouTube.
Jimmy Kimmel
But I started by blowing up her cigarettes. She's a world class smoker. She loves Marlboro Reds. She's been smoking, it's like a dragon, ever since I was a kid, you know, And I would get these cigarette loads. You remember those?
Craig Robinson
Oh, absolutely. We tried that on our dad.
Malia Obama
We sure did. We tried a bunch of stuff to make them stop smoking, quit smoking.
Jimmy Kimmel
That's not why I did it.
Craig Robinson
I know, I know. I got figured.
Jimmy Kimmel
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, 14, 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 thinks 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. Thank you. She'd be playing the video poker machines and just tobacco would go everywhere. Those things are the best.
Craig Robinson
Brazil, man. We did that to our dad and almost got in trouble.
Malia Obama
It was more. We were dipping the tips in hot sauce.
Craig Robinson
No you dipped the tips in hot sauce. I put one of those exploding things in his cigarette once, and it exploded. 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 from explosion.
Jimmy Kimmel
You are absolutely right.
Craig Robinson
It's bent from the explosion. It's just like a cartoon.
Jimmy Kimmel
If you get lucky and they take a hard drag, there will be tatters. You just have confetti coming out of your mouth. I buy them on ebay now, and they still work. You can't really find them new, but you can find them old.
Malia Obama
Oh, my gosh. Yeah.
Craig Robinson
And so going to school, did you get in trouble a lot at school doing stuff like that?
Jimmy Kimmel
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 Correspondence 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. I think he was a marine. And a good teacher, a really good teacher. Was an advanced level class. But there was. He did not like any screwing around in class. 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?
Craig Robinson
Yeah.
Jimmy Kimmel
And they said, hey, come on, whatever. And he goes. And he says, all right, you get one joke a week.
Malia Obama
Okay.
Jimmy Kimmel
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 would ruin my whole week. I'd have to wait, you know, Like, I'd be stupid, so I'd 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, he'd glare at me, and I'd go. I'd just give him, like, sign 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.
Malia Obama
Yeah. Yeah.
Jimmy Kimmel
And that's how I closed my White House correspondence 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.
Malia Obama
I'd say, you guess he remembered you, huh?
Jimmy Kimmel
Yeah, he did. He remembered me. You never know, right? I mean, there's a lot of students, but he remembered me. Yeah.
Malia 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.
Jimmy Kimmel
Yeah. Is it loyalty or just no one else wants us around? I don't.
Malia Obama
Deep love and loyalty.
Jimmy Kimmel
I have a lot of family and friends working at the show. I had a great childhood. I really did. I grew up in a real 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 great stars of the day. And he is now in my band. And his son was my band leader.
Malia Obama
Oh, yeah, yeah, yeah. I, you know, I know where you. Where you are with that.
Jimmy Kimmel
Yeah, yeah, he passed away.
Malia Obama
Yeah, yeah, yeah.
Craig Robinson
So when. When did you say, okay, maybe I can make a living out of this stuff?
Jimmy Kimmel
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, Perfecto. Perfecto in Motion was the name of the. And then there was another guy named Lovelace Watkins, who somehow my aunt and uncle befriended. But, you know, it wasn't something that I ever even imagined doing until I. I got on the radio. You know, that's really what I read. I love 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's 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. I remember my first. The first time I hosted a radio show, I 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 styled. Turned out it was only one star. And that star was John Davidson from. That's incredible. You remember that guy?
Malia Obama
Yeah, yeah.
Jimmy Kimmel
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. Of course, she and my mother had listened. My parents had listened to it, and they were so excited. And, you know, in the. Being raised in this loud Italian family, just being listened to, it was a big deal. And I think that was getting a word in edgewise. 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 there on.
Craig Robinson
Wow.
Jimmy Kimmel
Is be a disc jockey.
Malia Obama
Did you finish college?
Jimmy Kimmel
I didn't, no. 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. I stayed before I graduated as if I would have graduated.
Malia Obama
You weren't on the.
Jimmy Kimmel
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. So.
Malia Obama
What was his first job in morning radio?
Jimmy Kimmel
He was in Seattle at a radio station called kzok. It was my first paying job. I had a lot of jobs, like calling in and doing character bits, but none of them paid. But my first paying job was at kzok. I did a show with a friend called. His name was Kent Voss. The show is called the Me and Him Show. He was me, I was him. And we would. You were on air every morning and we loved it. We got fired 10 months into our one year contract. And then I had to.
Malia Obama
What happened? What'd you do?
Jimmy Kimmel
I just. Yeah. Would you. Would you blow up? I wasn't very diplomatic at the time. I was 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 where.
Malia Obama
Really.
Jimmy Kimmel
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 gonna live in Seattle forever, and this is gonna be our town. We're gonna be on the radio here. And then the next thing I knew was like, okay, grab your stuff from your desk and go home and don't come back. Which is weird.
Malia Obama
It's like, no notice.
Jimmy Kimmel
Yeah. You've never been fired, obviously.
Malia Obama
I don't think I have.
Jimmy Kimmel
No. Have you been fired?
Craig Robinson
I'm a coach.
Jimmy Kimmel
That's part of the business.
Craig Robinson
Yeah. Yeah. It is an empty feeling, isn't it? Yeah. Even when they owe you stuff, it's still like, oh, what am I going to do? 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. 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@airbnb.com host I try to always have a protein bar on me whenever I'm on the go. Something quick and easy that will still keep me satisfied, but with protein bars. It can often feel like you're choosing between taste and nutrition. If it tastes good, you flip the package over and suddenly there's a full paragraph of ingredients you can't pronounce. Artificial sweeteners, low quality protein fillers. I might as well just eat a proper dessert. I didn't want to have to choose between tasty and nutritious, so I kept searching until I found Aloha Protein Bars. Aloha bars are USDA organic and made with ingredients that are actually grown somewhere. That's part of their whole Taste that Grows philosophy. They use plant based ingredients grown in the ground, thoughtfully sourced and built to keep you satisfied. For example, their peanut butter cup Bar has 14 grams of protein, 10 grams of fiber, and only 5 grams of sugar, which is wild considering how delicious it is. It's made with absolutely zero artificial ingredients or fillers and it has become my go to snack. When Kelly isn't stealing them from my bag, that is. So if you're in the mood for something truly craveable and nutritious, try any of Aloha's protein bars. Grab one at your local grocery store or head to aloha.com.
Jimmy Kimmel
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.
Craig Robinson
Yeah.
Jimmy Kimmel
It's like you have something contagious and they don't want any part of it.
Malia Obama
It's like you used to be funny, but now.
Jimmy Kimmel
Yeah, you stink. Yeah. Like it really is. And I got fired a lot of times. It wasn't the only thing.
Craig Robinson
And that's what I was gonna say. You're like a coach get hired to get fired. How did you deal with those kinds of setbacks?
Jimmy Kimmel
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 that was nice. Having a teammate being fired with another person is easier than being fired on your own. 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 Kroc in LA, 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. I fit in well at that station.
Malia 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.
Jimmy Kimmel
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 KROQ 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 sports casts a morning 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 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, which has been great for me because I have to sit down and hash out a nine page monologue every night. But 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. 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 just keep going and going and going. And at the end of the night, the show's over and you're onto the next one and there's something terrible about that. It just disappears. You 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 stuff and that I like.
Craig Robinson
I would love to hear, Jimmy, about your getting your late night gig. Tell me about that process.
Jimmy Kimmel
It's a disappointing story. And it goes like this. I was 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 odds maker 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 wasn't doing it as a strategy, but it turned out to be a great strategy because people would drive them crazy. 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.
Malia Obama
You know, like, what are you turning
Jimmy Kimmel
down the idea that I Was turning down TV shows was genuinely ridiculous until he told me about this show, Win Ben signs 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. My manager is a guy named James Baby Doll Dixon. His other clients, Jon Stewart and Stephen Colbert, came along later. And 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, suggests to the guy, Lloyd Braun, who's running the company, that he 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 there like number one show, whatever. And for whatever reason, they decided they were gonna hire me, but they didn't wanna tell me. That's why they were interviewing me, because I had the same manager as the guy they had already essentially offered the job to. 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 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 gonna be hosted late. I talked to you, I was like, what? I am okay.
Craig Robinson
They knew about your strategy of saying no, so they made it so you couldn't say no.
Jimmy Kimmel
I don't think they knew anything about. It was a period of 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 100, 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 made you guys pick me over Jon Stewart? And he said, you were a lot cheaper, by the way. Was not kidding.
Malia Obama
No, no, Bob would not kid about that.
Jimmy Kimmel
And that's how I wound up on the air 23 years later. Here I am, cheap. That's all the discount host.
Malia Obama
That's right. That's right. What did it feel like making that transition?
Jimmy Kimmel
Terrifying.
Malia Obama
Really.
Jimmy Kimmel
Yeah, terrifying. Relentless. I mean, the show was live at that time.
Malia Obama
Yeah.
Jimmy Kimmel
And that means. And the show was on at midnight. It was on at 12:05 following Nightline. 12:05 to 1:05, which in LA time means 10:05pm to 11:05pm no. Yes. No. 9. Oh, sorry.
Craig Robinson
9:05.
Jimmy Kimmel
9:05. 10:05.
Craig Robinson
Yeah, yeah, yeah.
Jimmy Kimmel
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. Staff that 80% of them had never done anything like this before, had no idea what they were doing. A host who had no idea who he was doing, what he was doing. I had bunk beds in my office so my kids could sleep after school come and they'd 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 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 in fact, like the first six months, and 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.
Malia Obama
It's like, please.
Jimmy Kimmel
I really was.
Malia Obama
Put me out of my midst.
Jimmy Kimmel
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.
Malia Obama
Just hanging on. What do you think it was that kept it going? Was it the time slot? Was it luck? Was it bad luck?
Jimmy Kimmel
I think it's. Well, somehow we managed to get okay ratings, which I think is probably the number one reason that it stayed on the air, because if they weren't making money that, you know, whatever.
Malia Obama
So they're not doing you any favors.
Jimmy Kimmel
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. But I think more than anything is I'm just bullish. And I just kept. 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 do everything in my power to keep it going. And 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 has, you know, got this entirely different career. But back then there was. You were gone. That was it. You were done.
Malia Obama
Yeah. Yeah.
Jimmy Kimmel
Maybe you'd get a game show if you were lucky.
Malia Obama
Yeah. How old 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.
Jimmy Kimmel
They were at that time. My daughter was. My daughter Katie was 10 and my son was 8. My son Kevin was 8.
Malia Obama
They were little.
Jimmy Kimmel
Yeah, they were little. They were almost exactly the age that my younger kids are now.
Malia Obama
Yeah. Do they. What do they remember about that time or do they remember anything about that?
Jimmy Kimmel
They do. 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. 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. 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.
Malia Obama
Yeah.
Jimmy Kimmel
I'd get my son a bean and cheese burrito from Piquito 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. 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.
Malia Obama
Yeah, yeah, yeah. What's. What does your daughter Do.
Jimmy Kimmel
My daughter is an artist. My oldest daughter, 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.
Malia Obama
Nice.
Jimmy Kimmel
And she has a baby as well. So I am a grandfather. Welcome. Thank you.
Malia Obama
What do they call you? Pop. Pop.
Jimmy Kimmel
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.
Craig Robinson
So any tips on working with family? Because this is our first go around.
Jimmy Kimmel
Oh, yeah. Well, I think it might be harder with you guys because you're playing the same role here, whereas I guess that's true, you know, I'm in charge, you know, Although that's not great. And 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, or as far as working hard goes, as far as not complaining goes, as far as doing what needs to be done, they know that they have to be in the top 10% as far as that stuff goes. And I've been fortunate. I've had a couple of unfortunate situations. I've had to fire relatives. I've had to scold my uncle. Had to call him into my office and lecture him.
Craig Robinson
Yeah, that would be uncomfortable.
Malia Obama
Aw. And then how was Christmas after that?
Jimmy Kimmel
Well, he got over it quickly. But, you know, my Uncle Frank used to be like. He was a security guard on the show alongside Guillermo, who's my sidekick now. But Uncle Frank was my first sidekick, and he was the one we followed out to Las Vegas, who worked for Frank Sinatra. And he was a character. He was just offbeat, funny, dense man who. You could pull anything over on him. And 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, talking about dating and food and places to go and things to do, and it's just an unbelievable.
Malia Obama
Is that on you too?
Jimmy Kimmel
It is, yeah.
Malia Obama
Yeah.
Jimmy Kimmel
It's just unbelievable.
Malia Obama
I got so much to do after this.
Jimmy Kimmel
The guy doing Kermit was like, I don't know what's going on here? Is this a joke on me?
Malia Obama
So why did he get fired?
Jimmy Kimmel
Oh, I Didn't fire him. Oh, I just wasn't one of the ones.
Malia Obama
Okay.
Craig Robinson
Oh, you had a talking to. He got called into the office.
Malia Obama
Yes. So what did he get called, can you say?
Andrea (Listener)
Or is.
Malia Obama
It doesn't matter.
Jimmy Kimmel
No. Any 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, which, you know, like, part of the fun when somebody is, you know, a stooge, for lack of a better term, is you put them in situations they don't necessarily want to, 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 going to do that. And I'm like, yeah, you are going to do that.
Malia Obama
You are still a st. You're a star, but you're a stooge.
Jimmy Kimmel
We need you to do all the things, not just the fun ones. Yeah. So. But, yeah, he was funny, and he really helped get me through a lot of 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.
Malia Obama
So when did you meet Molly?
Jimmy Kimmel
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 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 years after that that we started dating.
Malia Obama
Yeah. Molly is everybody's favorite person.
Craig Robinson
Wait, let's back up a minute. So it was a couple years after you made her head writer that you started dating?
Jimmy Kimmel
Yeah.
Craig Robinson
When did you start thinking she was interesting?
Jimmy Kimmel
Oh, you know, I know it sounds. It always sounds like phony or whatever, but when I was dating, I was dating comedian Sarah Silverman. It didn't. I am. I don't like. I don't have that kind of brain.
Craig Robinson
So you had a girlfriend at the time?
Jimmy Kimmel
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 I broke up with my girlfriend, I just like, you know, you get in that period, you're like, ah, 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 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. I was like, it'll be fine.
Malia Obama
You're like, I'm the boss. It'll be okay.
Jimmy Kimmel
It'll be okay for me. But I also went from, you know, a 13 year marriage to an eight year relationship to dating Molly. So I've never been in a situation where I've been, like, dating, you know, I've never had anything like that. Not on the app. Yeah. That's not my. Yeah. There weren't even apps.
Malia Obama
There weren't even apps.
Craig Robinson
So you said earlier you don't know what writer's block is. You don't get writer's block. You're just used to cranking out stuff.
Jimmy Kimmel
Yeah.
Craig Robinson
Have you ever cranked out anything where you're like, ooh, I'm nervous about doing this, or, oh, every day. Really?
Jimmy Kimmel
Yeah. But I tend to lean into those things. 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. And really, that's why I was fired from all those other jobs, is because I always thought, oh, they'll think this is funny.
Malia Obama
Yeah, right.
Jimmy Kimmel
He'll think it's funny. I don't think they're gonna think it's funny.
Malia Obama
It's like, you're fired.
Jimmy Kimmel
I'll give you an example of something terrible I did.
Malia Obama
Yes.
Jimmy Kimmel
This was today.
Malia Obama
Oh, okay.
Jimmy Kimmel
Today is Ash Wednesday. Right, Right.
Malia Obama
Oh, I forgot about that.
Craig Robinson
You forgot about that?
Malia Obama
I did. Okay. Anyway, because we've been in this building
Jimmy Kimmel
all day, so my friend comedian John Mulaney texted me and Stephen Colbert and said, you guys have. You guys wearing. You have ashes. You know, we're all Catholic. You guys have your ashes today. And Stephen sends back a picture of himself, and he's got a. It looks like he got hit with a charcoal briquette. You. And then I am, like, kind of looking at the picture, and I think, oh, this is, you know, this is funny. What a mess this priest made on his thing. And I go into the bathroom and I get a pastel and I draw a penis on my forehead. And I texted, and I'm like, I guess my priest thinks he's funny, you know? And I thought, oh, maybe I'll put that on Instagram. And, yeah, no, that got. My wife was like, no, you're not. You will not.
Malia Obama
But if it were up to you, it had been sin. Sin.
Jimmy Kimmel
Left to my own devices, yeah, I probably would have done that. And now, in a way, I got. You know what? I kind of got what I needed because I did tell the story,
Malia Obama
and we're not laughing, everyone.
Jimmy Kimmel
I even said it to 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 went to church this morning and let me know if you think 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,
Malia Obama
and you crack yourself up.
Jimmy Kimmel
I love. You know, my other straight man growing up, besides my Aunt Chippy, who was my, you know, I would torture, was my priest, Father Bill.
Malia Obama
Oh, no.
Jimmy Kimmel
Who I've been friends with since I was a kid, you know, but there's no better. There's no one who can be more. Who gets more. You get more shock value out of. Than the priest from your church. And he had a great sense of humor. So he always started. 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.
Malia Obama
That's just like.
Jimmy Kimmel
So I had a painting made of Father Bill to celebrate the occasion. And I had it on an easel, and I had a sheet hanging over it. I was gonna 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. Oh, my God. Sitting on a stool, covering himself in just the right spots. It was just great. It was really, really like. I love when I'm doing the same things I was doing when I was 14.
Malia Obama
Oh. So how does it feel that you have probably unintentionally entered into this space in comedy where you are, you know, you've become a truth teller. And, you know, and there are times when. And, 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 has that transition felt for you because at heart you're a prankster, you know, you know, you're a morning show radio guy, you know, but here we are in these times and you have so bravely and boldly used your platform to speak truth to power, as they would say.
Jimmy Kimmel
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 don't see that. I just can't imagine on those nights talking about anything other than what we are talking about. 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 my job, I've always said, since the very beginning, even when 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 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 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 comedians have been doing this for a long time.
Malia Obama
So true.
Jimmy Kimmel
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. And I do think that he would probably have a greater impact than any of us do. But I don't love those nights. I feel uncomfortable, I get emotional, 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 going to Talk about this. Am I going to talk about this? Am I going to talk about this? And 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.
Malia Obama
Yeah. Yeah.
Jimmy Kimmel
I wish we didn't have to do it. I hope there's a day that we don't anymore. We can just go back to fun.
Malia Obama
It would be nice. It would be nice.
Craig Robinson
Do you worry that comedians will censor themselves in this environment?
Jimmy Kimmel
I think what worries me most is when comedians warp their sensibilities for whatever reason. Do people censor themselves? I don't know. Do television networks censor themselves? Absolutely. Have they always censored themselves? Yes, but for different reasons. I was listening to you guys talk to Henry Winkler, and ABC wouldn't let him wear his leather jacket unless he was riding. Riding a motorcycle.
Malia Obama
That's right. Yeah.
Jimmy Kimmel
I mean, how quaint is that? You know, like leather jackets or some kind of.
Malia Obama
It's like.
Jimmy Kimmel
It's a political statement entryway to gang membership.
Malia Obama
If you look at it, you'll go blind.
Jimmy Kimmel
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 kind. It's. It's especially sad to me. It's especially sad to me because you look at. At, you know, you look at some of these. These comics and, you know, maybe they're not doing so great and they, you know, I'm gonna pick up this. This MAGA torch and maybe people will support me just because of that.
Malia 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, more than.
Jimmy Kimmel
More than you would not, I would
Malia Obama
bet, because there's a lot, you know, we saw it in the White House, you know, especially around the. 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 believe 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 winking and nodding that goes on. It's like, you know, and I think that does a disservice to the people who are following people. It's like, oh, how much do you believe in this stuff you're spewing? Because if you don't believe it, don't play with people's lives like that.
Jimmy Kimmel
Yeah, it's hard to, on 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 a little more backlash than someone who maybe like Jon Stewart, who kind of came out of the chute of very outspoken liberal. Because I didn't talk about politics and because it wasn't really part of my, it wasn't really something I wasn't particularly interested in.
Malia Obama
You were putting bombs in cigarettes and sending Shippy off with the.
Jimmy Kimmel
Doing sports jokes and this kind of stuff and hosting the man show, which people were like, what? You've betrayed us? No, I've always been like this. My parents are. And of course that's how it starts. Whatever your parents are, usually that's what you are. And, and my parents are very liberal people, you know, Very, very, very liberal people. And I always have been, you know, I've, I've never voted for a Republican in my life. Just always been of this mindset. And I think people were like, just shocked to hear it because you assume somebody you like thinks like you. And I don't mind if people think differently. I have, I have some very close friends who, who think very differently. And I'm okay with that. 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 and just you have to allow for that. And lately I posted something on Instagram about some of these, primarily podcasters who now are having second thoughts about who they endorsed for president. And I'm grateful to them for being honest and admitting that they were mistaken. Absolutely. It happens almost never.
Malia Obama
Right. That people admit when they're wrong.
Jimmy Kimmel
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 basis of the whole faith is asking for forgiveness and 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.
Malia Obama
Right.
Jimmy Kimmel
That's what I think. Now 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.
Malia Obama
Yeah.
Craig Robinson
What makes you Excited about the future of comedy.
Jimmy Kimmel
I love the niche 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, 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, and then they put you on a little more, and then hopefully you get better. But now you open up your computer, you could do a whole show for 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, the end of comedy as a business. But I think it's great. I mean, I think you'll see a lot more people doing it. 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.
Malia Obama
And there are so many funny people out there. I mean, it's like, you know, I get funny things sent to me. Cause I try not to be on social media a lot, but I could spend the day just cracking up about people.
Jimmy Kimmel
I love that too. 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, and I like that.
Craig Robinson
Who are some of the younger guys that you see coming along that excite you? Can you say without.
Jimmy Kimmel
Without, like, thinking too hard? You know, that's always. I always get nervous because I will go home and go, oh, I forgot all about him.
Craig Robinson
He's gonna kill me.
Jimmy Kimmel
We had a comic named May Martin on the show last week who was very, very funny. And that's one of the great things about my job is sometimes I can see people and I can put em on television if I want to, you know.
Malia Obama
But we've got a listener question too.
Craig Robinson
We do, we always have a listener question that we can offer some advice to some. One of our listeners.
Andrea (Listener)
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, 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.
Jimmy Kimmel
Well, number one, I would. Andrea, your husband comes first no matter what he. Oh, sorry, I'm talking to Molly.
Craig Robinson
We were ready for that one.
Jimmy Kimmel
That's a tough one, especially for women because you know, there's, you know, these presumptions that you like. I guarantee you it, 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, then sometimes at night. 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 it 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, 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 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.
Malia Obama
She wasn't complaining.
Jimmy Kimmel
Let him do.
Malia Obama
She would have heard about it.
Jimmy Kimmel
Let him do his job, and you do your job, and then you do as much of the job together as you can and release that, 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. I'm not doing enough at, 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. She says this the other day. I'm like, what am I all. I think I was. What can I say to get out of this room without causing.
Craig Robinson
Getting yelled at?
Jimmy Kimmel
And what I did was I touched her on the face and I said, you're doing a great job. You're doing everything you can, and that's all you can do. 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.
Malia Obama
And scene.
Jimmy Kimmel
And there he goes, off to work.
Malia Obama
What a great man. What a great man.
Jimmy Kimmel
But it's hard, right?
Malia Obama
Yeah.
Craig Robinson
Yeah, it is.
Malia Obama
Yeah. 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 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 learn to play on that guilt. And that may not be. 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. Right. We learned that in the White House. So we started going. Okay. Yeah. We 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 regular routine and their lives 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.
Jimmy Kimmel
So much better than my advice to Andrea. 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 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, you know, you should. Your birthday's in July, and you should put that on your birthday list then if you want it. But we're not buying a jelly cat right now. And they go back, and my daughter's relentless. You know, she's going on, and she's like, but I did this and that. And so no Jane. I said, no, you know, whatever. And I'm sitting there, I'm watching the whole thing, and finally I go, go, I'll buy it for you.
Craig Robinson
Sorry, Jimmy.
Jimmy Kimmel
And I just. And they both started cracking. I decided, I'm just going to be the worst parent imaginable.
Malia Obama
I'm going to end this jelly cat issue. It's yours.
Jimmy Kimmel
I'll buy it for you.
Malia Obama
Here's two.
Jimmy Kimmel
And it was such an antisocial act that. But I did buy it for her, ultimately. And no lessons were learned.
Malia Obama
None whatsoever. You just screwed Molly. That's all.
Jimmy Kimmel
You did so brazenly, though, that I felt it was okay.
Malia Obama
Totally ran over you, backed over Molly and then drove back over her. Oh, my goodness.
Jimmy Kimmel
Good luck, Andrea.
Malia Obama
Yeah. Yeah. You're gonna be fine. You're gonna be fine. Well, this has been Great.
Jimmy Kimmel
Yeah, it was a lot of fun.
Malia Obama
Yeah. What's next? Next on the Jimmy Kimmel train.
Jimmy Kimmel
Let's see. I have an appointment with my ENT on Friday. Is that interesting? Nothing. You know, we're off for the rest of the week. I will rest up and then go right back at it.
Malia Obama
Go right back at it.
Jimmy Kimmel
Right back into the mess.
Malia Obama
Yeah.
Jimmy Kimmel
And it is a mess.
Malia Obama
It's a mess. But you handle it beautifully.
Jimmy Kimmel
Oh, thank you.
Malia Obama
You really do.
Jimmy Kimmel
I finally handled something beautifully in my life.
Malia Obama
Yeah.
Jimmy Kimmel
Well.
Malia Obama
Yeah. You've got this one down.
Craig Robinson
You've got this one down. It's fun watching you.
Malia Obama
Yeah.
Jimmy Kimmel
Thank you.
Malia Obama
And thank you for gracing us. You know, turnabouts.
Jimmy Kimmel
Finally.
Malia Obama
How did it feel being on the other side of the interview chair?
Jimmy Kimmel
It's fun, actually. You know, I like talking to you guys. I love the brother sister dynamic. I could probably ask you 10,000 questions about that.
Malia Obama
Just start with, yeah, we'll both be on.
Jimmy Kimmel
That would be fun.
Craig Robinson
That would be funny.
Jimmy Kimmel
Maybe on, like, National City Siblings Day or something like. That would be nice.
Malia Obama
And we could play a joke on Craig.
Craig Robinson
Oh, well.
Malia Obama
But he'll forget about it.
Jimmy Kimmel
Or we could just do something. You could just both do something to Aunt Chippy.
Malia Obama
Oh, great. Oh, my God. No, no, I don't.
Craig Robinson
Because I do not want to be responsible for any kind of accident.
Malia Obama
It's like. I don't know.
Jimmy Kimmel
Listen, I'm gonna kill her eventually. My son. Well, go out. You know, an A level.
Malia Obama
Oh, Jimmy, thank you so much for everything you're doing. We love you.
Craig Robinson
Love you.
Jimmy Kimmel
Love you, too. Thank you, guys.
Malia Obama
Thanks, Sam.
Episode: Have a Good Laugh with Jimmy Kimmel
Date: April 15, 2026
Host: Higher Ground
Guests: Jimmy Kimmel
Length: ~1 hour, 22 minutes
In this lively episode, Michelle Obama and her brother Craig Robinson are joined by late-night legend Jimmy Kimmel. Together, they swap stories about family, career ups and downs, pranks, and the evolving landscape of comedy. The conversation is full of laughter, heartfelt reflections, and candid insights about balancing high-pressure careers with parenting and staying true to your comedic voice in turbulent times.
Fashion and Airbnbs:
The hosts open with light teasing about Craig’s fashionable jacket and his extensive Airbnb experiences since the podcast began. Michelle shares her fondness for the word “janky” (02:30).
Mutual Kimmel Show Appearances:
Craig recalls his appearance on Jimmy Kimmel’s show, noting his wife Kelly forgot about it, leading to gentle ribbing. Jimmy confirms he remembers Craig’s visit (06:29).
Vegas Childhood:
Jimmy discusses moving from Brooklyn to Las Vegas at age nine due to a failed Florida move after an alligator encounter (13:32).
“I didn’t raise three daughters to have 'em eaten by a goddamn alligator.” — Jimmy’s Aunt Chippy (14:21)
Parents & Siblings:
His dad worked for a Howard Hughes company in casino IT, eventually running slot machine systems (21:26). Jimmy’s sister became a stand-up comic later in life, and his brother writes for South Park (22:23–22:39).
Practical Pranks:
Jimmy pranks his Aunt Chippy, including an elaborate self-driving car stunt at age 85 (24:16).
“No mercy.” — Jimmy, on family pranking (25:13)
He shares stories about exploding cigarettes and sibling mischief (25:16–26:44).
High School Jokester:
Teachers either loved or hated Jimmy—one limited him to “one joke a week” (28:26).
“Which is worse than no jokes…” — Jimmy Kimmel (28:26)
He closed the White House Correspondents Dinner with this anecdote (29:02).
Radio Beginnings:
Jimmy dreamed of being a cartoonist or radio DJ, landing a college radio show in high school (33:05).
“Just being listened to, it was a big deal.” (32:21)
First Firing:
Early jobs included a classic rock morning show in Seattle; he was fired in under a year, which was devastating (34:51).
“It really was, like, one of the worst times of my life…” (34:51)
Adapting Through Setbacks:
Frequent firings built resilience and adaptability, teaching him to write quickly and under pressure, a crucial skill for nightly monologues (39:38, 40:56).
“I never have writer's block because I just don’t have time for it.” (40:56)
How He Got the Gig:
ABC hired Jimmy Kimmel to host a late-night show—mostly because he was cheaper than Jon Stewart (44:41).
“You were a lot cheaper, by the way. Was not kidding.” — Bob Iger, per Jimmy (44:41)
Early Years’ Challenges:
The live show’s first years were chaotic, juggling single parenting, inexperience, and tight deadlines (45:56).
Staying Afloat:
Jimmy credits persistence and the support of family/friends on his team for surviving the tough years (47:11).
“It was just an act of sheer willpower more than anything.” (47:13)
Parenting While Hosting:
Jimmy often had his kids sleep in bunk beds at the studio as he balanced solo parenting and hosting (48:38–49:51).
“Our family traditions just took place at the show.” (49:24)
Working with Family:
Jimmy shares tips on working with relatives, emphasizing high standards and recounts the comedic chaos his Uncle Frank brought to the show (51:33, 52:29).
Meeting His Wife, Molly:
Molly started on the show as a writer’s assistant and worked her way up to head writer before they dated (54:02–54:45).
Risky Jokes and Censorship:
Jimmy admits he pushes boundaries in writing, often needing to be “talked out of” the riskiest jokes (56:23–56:57).
Anecdote: He drew a penis on his forehead for Ash Wednesday as a prank, texting it to Colbert and his childhood priest, who replied, “You need an exorcism.” (57:08–58:56)
Comedy as Truth-Telling:
On getting serious and political:
“To me, it just seems obvious and unavoidable... I just can’t imagine on those nights talking about anything other than what we are talking about.” (61:17)
Cancel Culture and Warped Sensibilities:
Jimmy discusses how comics sometimes abandon their real selves for an audience or a “hustle,” especially in today’s climate (65:00–66:44).
Audience and Social Media:
He’s excited about how social media allows niche comedy voices to flourish and reach audiences directly, though sometimes for less money (69:43–71:02).
Listener Andrea (72:44) asks for advice on balancing career and motherhood:
| Time | Segment | |----------|---------------------------------------------------| | 00:00 | Pranking Father Bill: The Nude Painting Story | | 04:47 | Guest intro: Both hosts on Kimmel's show | | 06:29 | Jimmy confirms remembering Craig’s appearance | | 13:32 | Brooklyn-to-Vegas childhood & alligator tale | | 21:26 | Parents’ careers and family roles | | 24:16 | Aunt Chippy and family pranks | | 28:26 | High school pranks; only “one joke a week” rule | | 33:05 | Radio start; impact of family support | | 34:51 | First major firing; lessons from rejection | | 39:38 | Skills built under pressure on morning radio | | 44:41 | ABC hires Jimmy Kimmel “because he’s cheaper” | | 45:56 | Live show chaos; single parenting stories | | 49:51 | Working with family on the show | | 54:02 | Meeting and working with wife Molly | | 56:23 | Pushing boundaries: risky jokes and consequences | | 57:08 | Ash Wednesday prank with Colbert & Father Bill | | 61:17 | Comic as truth-teller during hard times | | 65:00 | On comedians cashing in with political performances| | 69:43 | Social media and niche comedy’s future | | 72:44 | Listener Q&A: Working mom guilt and presence | | 75:21 | Jimmy and Michelle's parenting advice | | 78:18 | Jellycat story: undermining spousal discipline | | 81:05 | Closing banter: sibling dynamics and parting jokes |
This episode offers a generous mix of personal anecdotes, practical wisdom, and unguarded humor. Whether you’re interested in the nitty-gritty of show business survival, the challenges of working with family, or just need a laugh at parenting mishaps, Michelle, Craig, and Jimmy Kimmel deliver a memorable, insightful hour.