Craig Robinson reflects on a vibrant, humorous life shaped by late-night comedy, childhood pranks, and deep family bonds. The episode opens with a lighthearted yet significant moment—revealing a nude painting of his priest friend Father Bill at a 50th-anniversary celebration, blending personal friendship with bold comedic expression. Craig traces his journey from early radio work to becoming a late-night host, emphasizing resilience, persistence, and the importance of authenticity over polish. He credits his success to relentless effort, tight deadlines, and a willingness to push boundaries, even in serious moments. The story is interwoven with personal anecdotes: pranks on family, parenting during chaotic hours, and the role of humor in connecting with others. Craig also highlights how comedy, especially in today’s climate, serves as a tool for truth-telling and social awareness. He celebrates the human side of humor—pranks, small moments, and real emotions—while affirming that comedy is not just about jokes, but about reflecting life’s complexities. The episode is infused with warmth, nostalgia, and a deep respect for both personal relationships and the evolution of comedy over time, showing how laughter and honesty go hand in hand. Through personal and professional experiences, Craig underscores the value of authenticity, community, and staying grounded in everyday realities.
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?" I think that's just like, 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 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. Oh my sitting on a stool. This episode is brought to you by Shipped and Chase Home Lindy. Hey, Beach. Hi, Craig. Good. How are you? That's a good jacket. Have you worn that before? I wore this to the Christmas party. I haven't worn it on an episode yet. That's cool. It's cool on all fronts. The color is good. It feels smooth. Now can you get that in other colors? Yes, I have this in a different, I have a couple of these. I'll break them out later on. Yeah. So what's new and exciting? No, not much. Not much. No, not much. Man, you're boring. You know, I will say. So this trip to LA has been great. Now the sun's back out, but I've been, I've been 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 outfits soaked is easy. Well, we were just talking about how many Airbnb's do you think you've stayed in since we launched IMO because you, you, you know, you get around. I do. And so we've, I tried to figure it out. We've done 40 episodes, but you can't, you don't do one per episode. So you figure on average, we've done four or five. How many total tapings have we done in the last year team? And I'd say about 10 tapings separate tapings because once we started doing this, then I was just in my own personal life. I was doing Airbnb. So all your travel, your trips, the things with the boys, all of that stuff. So I would say since last August, so a year ago, August, probably 2025. 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 it. But he just so happened. You've been using janky a lot. I really love in 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. No. So speaking of janky. No, no, that's not right. We are our guests. This episode. 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. That's never happened, right? No, because no one invites you on their show. But Jimmy, when I did my book tour back in 2010, he invited me on. But my wife, Kelly Swar, who knows everything, Swar, that I wasn't on the Jimmy Kimmel show. She thought it was the other Craig Robinson. I don't know what you thought. But I was like, how do you forget that? How do you confuse that? Who would forget being on Jimmy Kimmel's show? I mean, the green room aspect of his show, the music. I mean, it's a good green room. It was a real memorable vibe as my kids would say. It was a vibe. It was drinks and food and music. Strippers. No, no, there weren't strippers. So that was only with me, right, Jimmy? So the male strippers. I didn't tell Baroque. But we were, you know, and I'm sure Jimmy wouldn't have remembered. If we were, 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. That you were right. I was right. Yeah, I would like to think you would forget to get home. I can't wait until Kelly that she was wrong. Well, let's properly introduce Jimmy Kimmel. Yes, let's do that. Jimmy Kimmel serves as host and executive producer of Jimmy Kimmel Live, which has become a picture 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. Oh, he's just hot because he's got those cute jeans on. Welcome, Jimmy. Come on in. Right, Jimmy. Look, look how cute his jeans are. Good. I'm cute. I'm good to see you, man. I want to tell you about your play. Look, look, you're here. I'm excited to be here. And thank you for saying my jeans are cute. I fredded over them before I came. My wife made me change. Tell her. She did. She really? Why is she? Why didn't she come? 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 and 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 it. So tell Kelly, you know what? I don't always remember if people have been on the show or not. Sometimes it gets blurred, but I definitely remember that. Thank you. Thank you for saying that. The weird to think that you might want to be concerned about is the fact that she doesn't remember. That's the thing. And Kelly, his wife remembers everything. So maybe no, I maybe she didn't remember him. Well, you know what it was. What that was one of the shows where I came alone. She usually she would come, come with me. But I think I flew down. I was in Oregon at the time. So I flew down. It may have been a blind spot caused by jealous rage. That's right. That's right. There you go. We were asking. So you're not sure when this is going whenever right now you guys are on a week. I ate us. We're on break. Yeah. Yeah. Yeah. How does how does that work? I mean, it feels like this talk show thing is pretty grueling. I mean, it is. It's grueling. So what's the week break feel like? Are you like chilling? Are you? It feels brief. I don't be dead. Actually, we rented an Airbnb in Phoenix. Really? We rented a, we went to visit our friends there. I have a friend named Chris Bianco. He's a great pizza chef. I think you have his pizza. Absolutely. 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. He 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. My gosh. They were very nice about it, though. They said so. So the car did he, did he trash the car? Did he total it? Trash. Our rental car was trash. It was, it was like a video game type scenario. He was so excited. Yeah, he was. It was sad. It was sad. It is so sad. But I told him, don't we're going to look back and laugh at this. So tell me this, did it have the old-fashioned gear shift that was on the side where you had them? No, it had that it was down. I know this because I drove it shortly before he drove it into the house. And it's so good. And I remember thinking this car's too fast. It's like, it's too responsive. You know, it's a little bit dangerous. Yeah, but it has to be in the right gear. It does. That's one of the things that we learned. Yeah. So if you're in, if you're in drive and should be reverse, it just doesn't work. So when that happens to your friend, are you laughing at him? Are you sort of like a buddy? 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. Uh-huh. And something ridiculous has just happened. I did have the urge to laugh, but I held it. I held it. We're laughing now. He's probably still not laughing. But maybe by the time this air is doubtful, but maybe here, uh, where the kids in the car? The kids were in, you know, the kids were in our rental car. And then 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. Did you get pizza at least? We did go, we did go for pizza afterwards. Because the kids were like, are we, because kids don't care. They're like, well, we thought we were getting pizza. 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. So that's what you do on your break. Yeah, no wonder it didn't feel long. You were dealing with crisis. Yeah. We took the kids to Vegas. We had a lot of fun in Vegas. So your kid, the little ones. Yeah. Right. 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. Kids love, there's a lot of fun stuff. Which I told them to stop saying out loud, you know, I believe they're like 10 and believe it's like, we love Vegas. We love staying at the wind. And I was like, you know what? Don't say that out loud. But it's made to attract little kids and old ladies like our mom. Kids like Blackjack. They love video poker. No, they love, we took them to see the Michael Jackson Circus. So they show, we went to see the Wizard of Oz at the sphere. It was like, great, really great. Yeah. Did they like it? I think a long time since doing very well. Yeah, that was fun. That was my aunt. She'd be along. She loves in Vegas. So we picked her up and brought her to the show. We went to a place called Omega Mark, which is part of this Meow Wolf. Franchise. He's visual experiences. And it's very interesting. It's really fun. There, I think there's one at Dallas, one at Phoenix, one at Denver or something, but it was a lot of fun. Kids loved it. And they got to stay in a room, a Vegas room. Whichever I actually died in it, you know, that kind of thing. Do you let them get in the mini bar? Because that can break you. We did not know. You know what? I don't think they even knew the mini bar was there. There's, I'm going to my kids knew. Oh, they did. Yeah. I can't even imagine. Well, candy bar. My dad would have done if we'd gone even open the door of a mini bar. But 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 drove back home. Those are the worst vacation. When you get towed back home, you heard my dad's mad. Everyone's quiet. Because we don't want them to get mad or you know. But 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 people back then wouldn't have taken somebody's dog. I mean, my hand knuckle 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 thinking 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. He's like, he thought he's like, let's just see. Let's just do not disturb on the room so the maids didn't come. Don't clean. Fluffy's not going to bark all day long. So Vegas, you were born in Brooklyn and moved to Vegas. What age? Nine years old. You were 90. So what prompted you to move? I just, 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 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 for New York does. They got to Florida. They put us small deposit on a house $100 on like a house that was going to be built in a subdivision. They're staying with friends. And in the backyard, the friends had a pool. There was an alligator in the pool of backyard. My aunt Chippy looked out. She goes, I didn't raise three daughters that haven't mean by a goddamn alligator. I'm with aunt Chippy. And that was that for Florida. That would be it for me. I've said this before. I don't like it's a reasonable fear. Any place where an alligator is going to could be in your backyard. It's like, 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, you're on Chippy. It's like everybody. We're out. We're out tonight. They lost $100. 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. My aunt should be still there. 86 years old. When was the last time you were shopping delivery service really delivered? I've had days when I'm bouncing between meetings, studio time, trying to get home before friends come over. And then I realized my grocery delivery guy made some creative choices. Like the time I asked for marinara sauce and they brought me salsa. 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Stop putting off those doctor's appointments and go to website. This episode of IMO is brought to you by Chase Home Lending. Buying a home isn't just a financial decision. It's a step into a new chapter and you shouldn't have to take that step alone. With Chase, you're supported by real people, your neighbors, folks you see around town, people who know your community and understand what matters to you. Chase's home lending advisors are there to listen, guide and help you understand what's possible and help you get into your new home. With smart digital tools like Chase My Home, you can plan your next steps and explore your options whenever it works for you. 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.
or 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 wanna be a vice president, act like a vice president. Those words stayed with me my whole career. Behave like the position you want, not the position you're in. So, if you're thinking about your own next chapter, remember, having someone you trust by your side can make all the difference. Explore your savings opportunities and let Chase support your journey. Visit chase.com/IMO to get started. Remember FDIC equal housing opportunity. (upbeat music) - What did your parents do? Did both your parents work? What did your dad do when he got to work? - 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 if he did. 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. - I remember that that's what they used to call IT. - Is that right? - Yes. - Yes. - My dad was an IT guy. - He was a genius. (laughing) - He's not a genius. But he did somehow run these systems that ran the slot machines at the casino and they would set the odds on the, that's as much as I know. - Oh, that's plenty, that's pretty good. - That's pretty good. - That's sometimes he'd be just clock in and go bowling and then have someone clock out for him. - Did you know that for a fact that you make it up? - I found that out a couple of years ago. (laughing) How many of you siblings do you have? - I have a sister and a brother. I'm the oldest, my sister's three years younger and my brother is nine years younger. - Are you the typical oldest brother? Are you the protector? Are you the, you know, where you beaten up? You're, you know, you're young. - I tortured them, yes, yes, I beat them. I did all the things that you supposed to do. - Did you really? - Yeah. Psychological torture. (laughing) But also I'm so much older than my brother. I was kind of like a brother uncle to him, really. - Yeah, yeah. - 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. - So you heard the reason why I South Park. (laughing) - I am none of the thing. - I have no manners. - My sister is a comedian, the stand up comic. - That's, that's wild. - Yeah, and you said she came to stand up comedy late in life. - Yeah, she decided about maybe like 13 years ago that she wanted to be a stand up comic. And everybody was like, what? - What did she do before that? - 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. - Wow. - Yeah. - Wow. - What's her brand of humor? - Her life being a mom and thing she notices. - I guess, I mean, I think that's what you'd call it. - Yeah, yeah, that's, that's, yeah. - Management Information Services, she does. (laughing) - 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. - 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 going up in your house? - 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. - Yeah. - 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. Our most recent mega prank on aunt Chippy was we put her in a Waymo, you know, the driver of this vehicle. And how old is she? - She was 85 at the time. Now she's 86. We put her in the car. We pretended that 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. (laughing) And the rest, you should just watch on YouTube because it's, I couldn't possibly explain how funny it is. - It's 85, Jimmy. - I did, you know what I did? She has three daughters, my cousins. And 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 hit send. Yeah, go ahead, go ahead, go ahead. So that's how it goes in our family. No mercy. God, I gotta see that, that's on YouTube. - What I started by blowing up her cigarettes. She's a world-class smoker. She loves marboral reds. She's been smoking. She's like a dragon ever since I was a kid, you know? And I would get these cigarette loads. Do you remember those? - Yeah, absolutely. - Yeah, we tried that on our dad. - We sure did. We tried a bunch of stuff to make them stuff smoke in. - She's making quit smoking. - That's not why I did it. I know, I know, I got a figure. 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'd think she got one over on me. She took the pack of cigarettes. And the next day I'd 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 best sale, man. - We did that to our dad and almost got in trouble. - It was more, we were dipping the tips in hot sauce. - No, you dipped the tips in hot sauce. We, 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 the cigarette in your mouth and it's bent. - You are absolutely right. - It's bent from the explosion. It's just like a cartoon. - If you get lucky and they take a hard drag, they will be tatters. Just, you just have this confetti coming out of your mouth. I buy them on eBay now and they still work. They like, they're, you can't really find them new, but you can find them all. - Oh my gosh. - And so going to school, did you get in trouble a lot at school doing stuff like that? - A little bit. - Yeah, a little bit. 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, like I think he was a Marine and a good teacher, you know, a really good teacher was an advanced level class, but he did not, 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 or the, 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? - Yeah. - And they said, hey, come on, whatever he goes. And he says, all right, you get one joke a week. - Okay. - 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, they 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 go, I just give him like, side 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, you're a funny guy, you're a smart kid. But if you keep screwing around, you're never gonna get anywhere alive. - Yeah, yeah, yeah. - And that's how I closed my White House correspondent 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 he, I guess he remembered me and he thought it was a funny story. - Well, I'd say you guess he remembered you, huh? - Yeah, he did, he remembered me. You never know, right? I mean, there's a lot of students, but he remembered me, yeah. - Wow, that's, 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, you, you, you go on onto people and they, they stay with you forever. - Yeah. Is it loyalty or just no one else wants us around? I don't know what it is. - No, I think it's love and loyalty. Yeah, I have a lot of family and friends working at the show.
I, 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 friends 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 band leader. Oh, yeah, yeah, I, you know, I know where you, where you are with that and yeah, yeah, yeah, yeah. So when, when did you say, okay, maybe I can make a living out of this stuff? You know, I always want 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 Chippie's house sometimes. And that was about as close as we got to show business. Yeah. Perfecto. Perfecto and motion was the name of the, 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 I, that I ever even imagined doing until I, I got on the radio, you know, that's really what 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'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 as 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, and I found a, 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, heat style turned out it was only one star. And that star was John Davidson from that's incredible. You remember that guy? Yeah. And we spent a full half hour talking about John Davidson's hair, which included a big white spot that was like a skunky, 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, and 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 from there on is be at this shocking. Did you finish college? I didn't know. I was at UNO V 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 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. So what was this first job in morning radio and it 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 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 was me. I was him. And 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. What happened? What'd you do? 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, 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. But they figured that out a lot quicker than I did and they, and they sent me back home. And it was heartbreaking. Really was like one of the worst times in my life where, 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, grab your stuff from your desk and go home and don't come back. Which is weird. It's like no notice. Yeah, you've never been fired, obviously. I don't think I know. Have you been fired? I'm a coach. Yeah, that's part of the, yeah, it is an empty feeling, isn't it? Yeah. Even when they owe you stuff, it's still like, 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. 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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. Yeah. 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. I went to another top 40 station and finally I wound up at K Rock 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. Yeah. I fit in well at that stage. Yeah. What do you think you were learning as you were going through this period in your life that prepared you for your ultimate shine? 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 sports casts of 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 non-stop 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.
around in a 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. 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 on to the next one. And if something terrible about that, it just disappears, you put as much work into 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. I would love to hear Jimmy about your getting your late night gig. Like tell, tell me about that process. 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, 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 turn out to be a great, 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. And then they keep offering me things until I did a game show called Windbend Steins money. And it was like, I think the fourth thing this producer Michael Davies had offered me in each time. I was just a, you know, I was the sports guy. I was making $60,000 a year, you know, like, what do you turn into? The idea that I'm turning down TV shows genuinely ridiculous. And until he told me about the show, Windbend Steins money, I was like, Oh, that sounds funny. And he explained the premise of the game show. And I was like, Oh, 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 Babydald Dixon, his other client. John 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 looked at a tape from, of me. And he said, Oh, the guy from the football and he's like, yeah, he's like, Oh, all right. So they looked at a tape and they are 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 going to hire me, but they didn't want to tell me that's why they're entering me because I had the same managers, 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 going to be hosting late night talk show. I was like, What? I am. Okay. They knew about your strategy, saying no. So they made it so you couldn't say no. They knew anything about it. 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 Baker, I was like, because I still to this day think they made a mistake. I would have at 100 times out of 100, I went to hire John 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 John Stewart? And he said, you were a lot cheaper. By the way, was not kidding. No, no, Bob would not quit kid about that. And that's how I wound up on the year. Right, right. 23 years later. Just cheap. That's all the discount host. That's right. That's right. What did it feel like making that transition? Terrifying. Really. Yeah. Terrifying, relentless. I mean, that's with the show was live at that time. Yeah. And that means, and the show was on at midnight. It was on a 12.05 following nightline, 12.05 to 105, which in LA time means 10.05 p.m. to 11.05 p.m. No. Yes. No, nine. I'm sorry. 9.05. 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. 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. 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 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, I hired all my friends, all my relatives. And there was a lot writing on this, right? And I was hoping that ABC would cancel the show. It's like, please, I really was because then it wouldn't have been my, you know, well, what are you going to do? I'm not quitting. But, you know, I wasn't going to 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 never came hanging on. What do you think it was that kept it going? Was it the time slot? Was it luck? Was it bad luck? I think it's, um, well, somehow we managed to get okay ratings, which I think is probably the number one reason that that stayed on the air. Because if they weren't making money, that we, you know, whatever. They're not doing you any favors. 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 I just kept, I had a good friend named Alex Wallow, who was the president of ABC at the time. And he said, at my 20 year anniversary, he said, you know what? 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, 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. Yeah. Now somebody like Conan is, you know, got this entirely different career. But back then there was, you were gone. That was it. You were done. Yeah. Yeah. Yeah. Maybe you'd get a game show if you're lucky. 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. They were at that time, my daughter was, um, a daughter Katie was 10. And my son was eight. My son, Kevin was eight. They were little. Yeah. They were almost exactly the age that my younger kids are now. Yeah. Do they remember, what do they remember about that time? Or do they remember anything about that? Do my son, Kevin, works at the show now. So he's still in the bunk bed. Yeah. He's six five. But he's showing 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 are 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, um, took place at the show. Yeah. I'd get my son a bean and cheese burrito from piquito moss every, you know, like we had my daughter again, Panay Marinerra from the Italian restaurant across the street. We do the homework. You know, I'd be riding 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's like just very strange situation. But, you know, what are you going to do? That's how you just have to do it. Yeah. Yeah. Yeah. What's, what is your daughter do? My daughter is an artist, my oldest daughter. Um, she, her name's Katie Kimmel, um, you can find her on Instagram. She's a very successful ceramics artist. She makes really clever, um, whimsical sculptures and, uh, she has a pop up store at the row in downtown LA. Nice. And she has a baby as well. Um, so I am a grandfather. Welcome. Thank you. What
they call you pop pop. 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 just, I'm going with grandpa. I don't know, I know it's weird, but I'm going to hope for just grandpa. So any tips I'm working with family because this is our first, our first go already. Oh, yeah. Well, I think it might be harder with you guys because you're playing the same role here, whereas, you know, I'm in charge. You know, 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 higher 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. 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. I've had this scold my uncle call him into my office and lecture him. Yeah, that would be okay. And then, and then how was Christmas after that? Well, he got over it quickly. But, you know, he, my uncle Frank used to be, look, 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 an 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 wants 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. Is that on YouTube? It is. Yeah, yeah. It's just unbelievable. I've had so much to do after this. The guy doing Kermit was like, I don't know what's going on here. Is this a joke on me? So why did he get fired? Oh, I didn't fire him. Oh, I just, it came close, it came close. Okay, so he had to talk to you. He got called into the office. Yes. So what did he get called? Can you say or is it a crime matter? No, it wasn't any better. 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 a, you know, a stooge for a lack of a better term is you put them in situation 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 in a life. Yeah, you are going to do that. You are still your star, but you're a stooge. 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. So when did you meet Molly? 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. Yeah, and Molly is everybody's favorite person. Let's back up a minute. So it was a couple of years after you made her head writer that you started dating. Yeah. When did you start thinking she was interesting? You know, I know it sounds, it always sounds like phony or whatever, but when I was dating, I was dating comedian Sarah Silverman. I don't have that kind of brain. So you had a girlfriend at the time. I had a girlfriend. 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 know, you get in that period you're like, I'm not going to go out, you know, it was a fairly high profile relationship, whatever. So I would just hang out at the show after work. We just hang out a group of us and Molly was a 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 much more cavalier about the whole thing. It'll be fine. You're like, I'm the boss. It'll be okay. 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. So I'm on the apps. Yeah, that's not my, yeah, there weren't even there weren't even apps. So you said earlier, you, you don't know what writer's block is. You don't get writer's block. You just used to cranking out stuff. Yeah. Have you ever cranked out anything or you like, oh, I'm nervous about doing this? Or really? Yeah. Well, 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 because 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. I don't think they're going to think it's funny. This is like, you're fired. I'll give you an example of something terrible. I did. Yes. This was today. Oh, oh, okay. Today is Ash Wednesday, right? Right. Oh, I forgot about that. You forgot about that? I did. Okay. Anyway, because we've been in this building all day. So my friend comedian, John Mulaney texted me and Steven 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 Steven sends back a picture of, of himself and he's got a, it looks like, it looks like he got hit with a charcoal briquette, you know. And then I'm like, kind of looking at the picture and I think, oh, this is, you know, this is a funny home. What a mess this priest made on his thing. And I go into the bathroom and I get a, a pastel and I draw a penis on my forehead. And I texted and I'm like, well, I guess my priest thinks he's funny, you know. And I said, oh, maybe I'll put that on Instagram. And yeah, no, that got in my wife was like, you're not. You will not. But if it were up to you, it would have been sent to my own devices. Yeah, 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 that with story. And we're not laughing everyone. I even sent it to my, my, 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, 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. And you crack yourself up. I love it. You know, my other straight man growing up, besides my aunt Chippy, who was my, you know, I would torture. It was my priest, Father Bill, 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 then the priest from your church. And he had a great sense of humor. So he always sort of 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 it this way? So I had a painting made of Father Bill to celebrate the occasion. And I had 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, covering himself in just the right spots. It was just great. It was really. really like I love doing the same things I was doing when I was 14 oh so how does it feel that you have probably unintentionally entered into the space and comedy where you are you know you 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 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 boldly used your platform to speak truth the power as they would say 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 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 and 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 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 that's what my job is and comedians have been doing this for a long time and you know from my generation George Carlin Richard prior 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 than any of us do but I you know I don't I don't love those nights it's not I feel uncomfortable I get emotional 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 going to talk about this am I going to talk about this am I going to 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 yeah yeah I wish we didn't have to do it I hope there's a day that we we don't anymore we can just go back to fun it would be nice it would be nice do you do you worry that comedians will sense of themselves in this environment I think I think it worries me most is when comedians warp their sensibilities for whatever reason do people censor themselves I don't know I don't do television network censor themselves absolutely have they always censor 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 a motorcycle that's right yeah I mean how quaint is that you know like leather jacket so it's like it's like it's the devil yeah entryway to gang membership if you look at it you'll go blind 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 it's it's especially sad to me it's especially sad to me because you look 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 you know I'm gonna pick up this this maggot torch yeah yeah and and maybe people will support me just because of that 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 more than more than I would bet 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 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 I 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 wink in a nodding that goes on it's like you know and and I think that is does it disservice to the people who are following people it's like oh do you 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 yeah it's um it's hard to I it's some some levels it's hard to understand on others it's easy to understand because when it comes to how people make their money they seem willing to compromise in in a lot of ways and I think I get a little more backlash than someone who maybe like like John Stewart who kind of came out of the the shoot of very outspoken liberal because I didn't talk about politics and it because it wasn't really part of my act it wasn't really something I wasn't particularly interested in you were putting bombs and cigarettes yes and send in I was mostly I was with the doing sports jokes and this kind of stuff and I'm hosting the man show you know which people like are like why you betrayed us like no I've never I've always been like this I you know my parents are you know of course you know that's how it stars it would 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 you know I've I've never voted for a public in my life just always been of this mindset and I think people are 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 I have I have some very close friends who think very differently and I'm okay with that I I understand that people have different life experiences and believe things I mean I know I personally believed certain things to be true for a long time my life and realize that they weren't and just you have to allow for that and lately you know 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 I'm grateful to them for being honest and admitting that they were mistaken I don't it happens almost never right that people admit when they're wrong 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 you know it's asking for forgiveness and that seems to be cast aside but I welcome those people I am I I don't think there's any way forward if we don't right that's what I think 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 yeah what makes you excited about the future of comedy I love the niche aspect aspect to comedy now where you can like our announcer on our show 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 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 know, 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 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'll be able to, if you're good, you can make a living and really only talk about what you want to talk about. And there are so many funny people out there. I mean, it's like, you know, 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. I love that too. It's 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 going to have like some incredibly developed talents that are very unique and very unusual. And I like that. Who are some of the younger guys that you see coming along that excite you? Can you say without, without like thinking too hard, you know, that's always, I was getting nervous because I will go home and go, he's going to get away. 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 them on television if I want to, you know, but we've got a listener question too. We do. We always have a listener question that we can offer some advice to some one of our listeners. Hi, my name is Andrea. I'm a mom of three-year-old twin girls and they're 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 save her 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 therefore, 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. Well, number one, I would, Andrea, your husband comes first, no matter what. He. Oh, sorry, I'm talking to Molly. We were ready for that one. That's the top one, especially for women, because there's these presumptions that you. I guarantee you if the roles were reversed there, be like, wow, what a great dad he is. He wouldn't be writing. He wouldn't be writing it like, how can I be more present? He'd be like, I'm with these kids all week and sometimes at night. But it does seem 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? They're still only 24 hours in the day. Now, we're expected to do so many more things. 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. That has to be enough because you have to be a 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 sounds like she thinks he's doing a good job. She wasn't complaining. Who would have heard about it? 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 guilt. My wife, we have this conversation too. She's like, I feel like I'm not, you know, I'm not doing 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. She says this the other day. I'm like, I wonder why I think I was, what can I say to get out of this room without causing an injury? And what I did was 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. 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 surge of pride in the way I handle it like you would in a movie. And there he goes off to work. What a great man. What a great man. It's hard, right? Yeah, it is. 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 you're, 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. 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 Baroque reacts to it, right? We learn 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 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. 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 birthdays 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 into and she, my daughter's relentless, you know, she's going on. And she's like, but I did this and that. And she's like, 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. Oh, Jimmy. And I just, and they both started cracking. I just said, I'm just going to be the worst parent imaginable. We're going to end this jelly cat issue. It's yours. I'll buy it for you. And it was, it was such an anti-social act. But I did buy for her ultimately. And no less. We're learned. Yeah. None, none, none whatsoever. You just screwed Molly. That's all you did. So brazenly, though, that I felt it was okay. Totally ran over. You backed over Molly and then drove back over her. Oh, my goodness. Good luck, Andrea. Yeah. Yeah. You're going to be fine. Well, this has been great. Yeah. It was a lot of fun. Yeah. What's next on the Jimmy Kimmel train? Let's see. I have an appointment with
my auntie 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 out. Right back into the mess. Yeah. And it is a mess. It's a mess. But you handle it beautifully. I think you really do. I finally handle something beautifully in my life. Yeah. Well, you've got this one down. Yeah. It's fun. It's fun watching you. Yeah. Yeah. And thank you for greasing us. You know, turn around. My pleasure to feel being on the other side of the interview chair. It's fun, actually. You know, I like talking to you guys. You're a mirror. I like to love the brother sister dynamic. I could probably ask you 10,000 questions about that just to start with. One day we'll both be on. Yeah, that would be fun. That would be fun. Maybe unlike national siblings day or something like that would be nice. And we could play a joke on Craig. Oh, well, he'll forget about it. Or you could just do something. You can just both do something to answer. Oh, great. Oh, my God. No, no, I don't. Because I do not want to be responsible for any kind of acts. It's like, I don't know. Listen, I'm going to kill her eventually. My soul go out, you know, an A level. Oh, Jimmy, thank you so much. Thanks for having me. You're doing. We love you. Thank you so much. Thank you guys. Your body is always changing and those changes can feel like a lot to navigate alone. Wait, that won't budge. Skin that starts to show signs of change, hair loss, mood swings, MIDI health gets it because MIDI was built for exactly this by women, for women. Their clinicians specialize in the hormonal shifts that occur throughout your life. So you're not getting generic care. You're getting expertise for exactly where you are. MIDI is the trusted virtual care clinic for women's health with specialists trained to treat everything from weight changes, to skin care, sleep, mood, and hormonal health. They listen, they dig into root causes and they build you a personalized care plan with treatments that fit your needs. You shouldn't have to keep guessing. And with MIDI, you won't. MIDI visits are available in every state and covered by most insurance plans. So expert care that actually sees you is more accessible than you think. Book your first virtual visit today at joinmitty.com. That's join m-i-d-i.com.
Podcast Summary
Key Points:
Craig Robinson shares a humorous story about revealing a nude painting of his longtime priest friend Father Bill at his 50th-anniversary celebration, which caused laughter and delight among bishops and attendees.
The episode highlights Craig’s lifelong prankster instincts, rooted in childhood practical jokes with family, especially his aunt Chippy, and carried into adulthood through comedy and satire.
Craig reflects on his career path from radio hosting to late-night television, crediting persistence and sheer willpower over luck for the longevity of his show despite early setbacks.
He discusses the importance of storytelling and honesty in modern comedy, emphasizing that truth-telling and addressing social issues are natural extensions of his comedic roots.
Craig shares personal connections, including his family, his career in media, and his relationship with Molly, a writer who became his partner after years of workplace camaraderie.
The conversation touches on real-life challenges, such as parenting during a demanding work schedule, and the joy of simple family traditions, like sharing snacks and helping kids with homework.
Craig praises Airbnb as a meaningful way to use homes while traveling, especially during events like the FIFA World Cup, noting its impact on community and hospitality.
He credits his ability to constantly create content—without writer’s block—to intense work routines and the discipline of deadlines, which shaped his comedic style and career resilience.
Summary:
Craig Robinson reflects on a vibrant, humorous life shaped by late-night comedy, childhood pranks, and deep family bonds. The episode opens with a lighthearted yet significant moment—revealing a nude painting of his priest friend Father Bill at a 50th-anniversary celebration, blending personal friendship with bold comedic expression. Craig traces his journey from early radio work to becoming a late-night host, emphasizing resilience, persistence, and the importance of authenticity over polish.
He credits his success to relentless effort, tight deadlines, and a willingness to push boundaries, even in serious moments. The story is interwoven with personal anecdotes: pranks on family, parenting during chaotic hours, and the role of humor in connecting with others. Craig also highlights how comedy, especially in today’s climate, serves as a tool for truth-telling and social awareness.
He celebrates the human side of humor—pranks, small moments, and real emotions—while affirming that comedy is not just about jokes, but about reflecting life’s complexities. The episode is infused with warmth, nostalgia, and a deep respect for both personal relationships and the evolution of comedy over time, showing how laughter and honesty go hand in hand. Through personal and professional experiences, Craig underscores the value of authenticity, community, and staying grounded in everyday realities.
FAQs
Craig revealed a nude painting of Father Bill sitting on a stool, covering himself in just the right spots, as a humorous tribute to their long-standing friendship. The painting was unveiled after a playful talk about their relationship, and it was well-received by the audience, especially with bishops present.
Craig was invited to speak at the event celebrating Father Bill's 50th anniversary of priesthood in Las Vegas. He created a painting of Father Bill as part of the celebration and used it to share a lighthearted, humorous story about their friendship.
Craig has been a close friend of Father Bill since childhood, and they share a humorous, playful relationship. Craig often makes jokes about the priest, and their bond is rooted in shared experiences and mutual respect for each other’s sense of humor.
During his break, he and his family visited friends in Phoenix, where they stayed at a beautiful house owned by a pizza chef named Chris Bianco. The visit turned into an accident when the chef’s restored El Camino was driven into the Airbnb, destroying part of the garage.
They took their kids to see the Michael Jackson Circus and the Wizard of Oz show at the Sphere. The kids loved the experience, and they also visited a Meow Wolf visual experience, where they stayed in a room and enjoyed the fun environment.
Craig began in high school on a college radio station, where he hosted a show and interviewed a hairstylist of a celebrity. The experience was exciting for him, especially since his family listened to it, which gave him a strong sense of validation and motivation to pursue a career in media.
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