Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)

Summary

Podcast Summary: "Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)"

Podcast Information:

• Title: On Purpose with Jay Shetty
• Host: Jay Shetty
• Episode: Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)
• Release Date: August 13, 2025

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1. Introduction to Jimmy Kimmel

The episode begins with Jay Shetty introducing his guest, Jimmy Kimmel, a household name known for his long-running late-night show. Jay highlights Jimmy's unique position of rarely being a guest on interviews, setting the stage for an intimate and revealing conversation.

Notable Quote:

Jay Shetty [01:12]: "Jimmy, you don't do a lot of interviews. What does it feel like to be on the other side?"

2. The Early Struggles and the Role of Pranks

Jimmy delves into his early career struggles, emphasizing how his penchant for pranks often led to multiple job losses. He recounts various humorous yet telling stories of how his antics, such as sabotaging golf carts and repeatedly placing hot dogs in his boss's desk, ultimately resulted in his dismissals.

Notable Quotes:

Jimmy Kimmel [01:27]: "Pure delusion."

Jimmy Kimmel [15:22]: "I have tunnel vision, you know, Like, I got stuff I need to get done, and I want to get it done."

3. Transitioning from Radio to Television

Despite frequent setbacks, Jimmy's resilience and unique comedic style eventually opened doors in radio, leading to opportunities in television. He attributes much of his eventual success to luck and being prepared to seize moments when they arose.

Notable Quote:

Jimmy Kimmel [07:08]: "A lot of it is luck... You have to be ready when you get that moment."

4. Personal Life: Marriage and Family

The conversation shifts to Jimmy's personal life, particularly his relationship with his wife, Molly. They share anecdotes about their 16-year relationship, highlighting Molly's significant influence on Jimmy's personal growth and maturity. Jimmy humorously discusses their dynamic, including Molly's role as an executive producer and the playful teasing that defines their relationship.

Notable Quotes:

Jimmy Kimmel [32:56]: "We are celebrating our 12th anniversary in July."

Molly [37:37]: "Jimmy is incredibly self-deprecating if you can't tell..."

5. Becoming a Grandfather: Reflections and Anticipation

Jimmy expresses his excitement about becoming a grandfather, sharing lighthearted plans to prank his grandchildren as he did with his own family. He reflects on the cyclical nature of family dynamics and the enduring aspects of his personality that he hopes to pass on.

Notable Quotes:

Jimmy Kimmel [23:21]: "Katie had a baby. A baby girl."

Jimmy Kimmel [24:44]: "Anxiety... They find different paths to it. It has nothing..."

6. Dealing with Anxiety and Relationships

A significant portion of the discussion addresses Jimmy's experiences with anxiety, both stemming from his early financial struggles and in his current life of fame. He elaborates on how his relationships have been tested by financial expectations and the pressures of being a public figure. Jimmy emphasizes the importance of therapy and self-reflection in managing his mental health.

Notable Quotes:

Jimmy Kimmel [29:22]: "It's just hard to explain to people when they want money, but your relationship with them is more important than that money."

Jimmy Kimmel [40:04]: "There's a lot of stuff in there. I'm not sure I want to go rummaging around. There's a whole pizza in there."

7. The Impact of Late-Night Success on Personal Growth

Jimmy discusses how achieving success in late-night television allowed him to nurture his authentic self and comedic expression. He reflects on the balance between staying true to his comedic roots while evolving as a person and professional.

Notable Quote:

Jimmy Kimmel [20:35]: "Pure delusion... I wasn't that good at my job."

8. Final Five: Quickfire Questions

In the concluding segment, Jay Shetty poses five rapid-fire questions to Jimmy, eliciting candid and often humorous responses. This segment provides deeper insights into Jimmy's personal philosophies, values, and lighter aspects of his personality.

Sample Questions and Responses:

• Best Advice Received:

  Jimmy Kimmel [45:49]: "Listen to a priest... I just listened to them. Good advice."

• Worst Advice Received:

  Jimmy Kimmel [48:07]: "Lash out is the worst... you gotta take a beat."

• Morning and Night Routines:

  Jimmy Kimmel [48:45]: "Brush my teeth... snuggle with my kids."

• Valued Once but No Longer:

  Jimmy Kimmel [49:34]: "I don't drink much anymore."

• One Law for Everyone:

  Jimmy Kimmel [50:18]: "The golden rule. Do unto others."

Notable Quote from the Final Segment:

Jimmy Kimmel [50:18]: "If we all did that, we'd be doing great."

9. Concluding Thoughts and Reflections

The episode wraps up with reflections on the importance of empathy, gratitude, and continuous personal growth. Jimmy underscores the value of meaningful relationships over material success and the significance of supporting others to find personal fulfillment.

Notable Quote:

Jimmy Kimmel [42:00]: "Helping other people is always a help. It always makes you feel better."

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Conclusion:

This episode of "On Purpose with Jay Shetty" offers a candid and multifaceted glimpse into Jimmy Kimmel's life beyond the spotlight. From his early career challenges and love for pranks to his roles as a husband and new grandfather, Jimmy shares personal stories that reveal the resilience, humor, and depth behind his public persona. The insightful discussion on anxiety and relationships provides listeners with relatable experiences and valuable lessons on navigating personal and professional growth.

Transcript

[Jay Shetty]

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[Jimmy Kimmel]

It feels selfish sometimes to be happy. It's hard to figure out to be happy. There's no logical reason why we shouldn't be happy. It doesn't make sense.

[Jay Shetty]

Jimmy Kimmel's been hosting his late night.

[Jimmy Kimmel]

Show for over 20 years.

[Jay Shetty]

Jimmy, you don't do a lot of interviews. What does it feel like to be on the other side?

[Jimmy Kimmel]

Putting yourself out there is hard. I started in radio. You're already halfway hidden. Nobody sees you. You don't have an audience there to not laugh if you're not funny when.

[Jay Shetty]

Everyone'S firing you, letting go of you, telling you this isn't a great idea. How do you hold on to an idea when everyone's telling you it's terrible?

[Jimmy Kimmel]

Pure delusion.

[Jay Shetty]

Has talking about your emotions always been something that you found challenging?

[Jimmy Kimmel]

I feel like I've matured a lot, thanks to my wife.

[Jay Shetty]

In what way?

[Jimmy Kimmel]

No, don't ask her. Oh, she's standing. She wants to be asked. All right, before she gets up here, Jay, I should just say you've been.

[Jay Shetty]

Very open about your son's heart condition. And that's been something that I imagine.

[Jimmy Kimmel]

Is extremely difficult to stop and think about someone else and their child. The number one health and wellness podcast, Jay Shetty. Jay Shetty, the one, the only Jay Shetty.

[Jay Shetty]

I am so excited to be here tonight at the Greek Theater in LA with the one and only Jimmy Kimmel. Make some noise, everyone.

[Jimmy Kimmel]

Thank you. Thank you for having me. Jay, I want you to know that my first question, as it always, is because I'm never. I'm interested. I was watching you and when you had people stand up and you said, stand up if you've ever worried about how you looked. And I was thinking, I was wondering. Cause I couldn't see the audience. If anyone didn't stand because I think everybody. And if there was a person who's never worried about how they looked, that's the person I want to hang out with after the show. But I said, what is the dress? You know, what is the. Cause I want to fit in. They said, it's elevated casual. I was like, all right, well, okay, I'll find something that seems to fit that category. And then I come here, and you are dressed like Adam Sandler.

[Jay Shetty]

I'm not wearing shorts. I'm not wearing shorts.

[Jimmy Kimmel]

Is this technically elevate. What is it elevated from?

[Jay Shetty]

I don't know what this is, but I assume this is what you wear.

[Jimmy Kimmel]

To go to 7 11. There's nothing. This is just casual. This is not. This is just level casual is what it is.

[Jay Shetty]

Jimmy, this is not the roast of J.C. i think you're at the wrong. I think you're at the wrong event. I think we're gonna see you stand.

[Jimmy Kimmel]

Up if you've ever eaten a whole pizza by yourself.

[Jay Shetty]

All right, Jimmy, we're three minutes in, and you started roasting me already.

[Jimmy Kimmel]

I'm sorry. It's my nature. I was telling you it was confusing to me because you're talking to these people, and everybody's got these great stories, and you're hypnotizing them with your eyes. I know what you do. You know, like, 85 of this audience is here in the hope they might get to have sex with you. Right. That's why I showed up.

[Jay Shetty]

So how does this go, Jimmy? How does that work between me and you?

[Jimmy Kimmel]

What, sex?

[Jay Shetty]

Yeah.

[Jimmy Kimmel]

Well, when a host and his guest fall very much in love, they go into the dressing room and. And I'll show you from there.

[Jay Shetty]

Yes, that's right. My wife would not approve. Thank you so much. That's the only reason. Thank you so much, man. I appreciate it. Jimmy, you don't do a lot of interviews, but you.

[Jimmy Kimmel]

No one wants to talk to me.

[Jay Shetty]

You agreed to do this one. Why now? Why here? And what does it feel like to be on the other side?

[Jimmy Kimmel]

First of all, my wife loves you. And so I've become exposed to you, your magic. We have some mutual friends. And really, I said to my wife, I said, hey, Jay Shetty asked me if I would do his show. I said, what do you think? She said, well, I'd like to hear you on that. And I said, all right, well, you're not listening to me at home, so maybe. Maybe we can accomplish something today.

[Jay Shetty]

We'll make some magic happen. Where is she? Is she here?

[Jimmy Kimmel]

She is here, but I don't know where she's sitting. She may be.

[Jay Shetty]

Hello there.

[Jimmy Kimmel]

Oh, there she is. If you guys want to thank you for making this happen, write on a card what you think of her. We'll hand them to her afterwards.

[Jay Shetty]

Thank you for making this happen, Jimmy. Let's start there. Actually, you know, tonight has been all about what we don't do because of what people think of us, the things we worry that people are perceiving about us, the judgments, the criticisms that people have of us. Talk to me about a time in your life when you really felt, like, imprisoned by that, if ever.

[Jimmy Kimmel]

Oh, very much so. All the time. Not just. I mean, really honestly, like, if I'm at an event and I'm not dressed properly. I feel. In fact, I went to a wedding recently. A very good friend invited me to be in his wedding party. And he was not great with the details of the party, but again, another dress code situation. This one was festive attire, which means nothing to me. And I was in the wedding party, and I wore what I thought was festive attire. And I showed up and everyone else was in a black suit. And so I'm the idiot in all these wedding photos. And that, you know, that's. I feel uncomfortable with the simple things like that. But, you know, putting yourself out there is hard. And I'm not talking about show business necessarily. I think that there are a lot of people that I've known over, you know, years and years who are really good at something, and you try your best to encourage them to do that thing that they're good at, and they're either going to do it or they aren't. And sometimes for them, you saying they're good at it is enough. That's enough for them. And they don't want to threaten that idea. They don't want you to ever think, oh, you weren't good at that. So they leave it. And I think that's. To me, that's so sad that people. People will do that, because I do think that there are so many people who know they have this potential or this talent or whatever it is, and they just. They don't use it because they don't want to be proven otherwise. Because everyone in their little circle thinks it, and they don't want to change their minds. And I know that's an inelegant way of saying it, but you just really need to do it. You have to do it. And I. For me, I was fortunate because I started in radio, and when you're on the radio, you're already halfway hidden. Nobody sees you. You don't have an audience there to not laugh if you're not funny. So you just kind of have to assume you were, and you keep going. And I was able to take baby steps from being on the radio to being the sidekick on a game show, to being a partner on a comedy show, to eventually doing my own show. And I'm not sure if I would have been able to take that big leap. I was fortunate, really, genuinely fortunate. Very lucky to have been in a situation where I could take those steps one by one. Oh, yeah. I mean, it's just a lot of it is luck, you know, that's the other thing. That is a sad truth, but a lot of it is luck. Now, you have to be ready when you get that moment, or you are lucky when you have that moment of fortune. You have to be prepared, and you have to do whatever it is that you need to do to accomplish whatever goal you would like to accomplish. But still, luck is a big part of it.

[Jay Shetty]

Yeah, I want to get to that, but I want to go backwards a little bit, because I read somewhere that you actually grew up wanting to be a scientist.

[Jimmy Kimmel]

No, I don't know where you read that, but that is false.

[Jay Shetty]

Okay.

[Jimmy Kimmel]

Was I farting into Ziploc bags and leaving them under my sister's pillow? Yes, if that's what you consider to be science. I wanted to be a scientist, but no, science was never my thing. I wanted to be an artist. When I was a kid. I liked to draw. That was my thing. I wanted to draw.

[Jay Shetty]

And you were good at drawing?

[Jimmy Kimmel]

Yes, I liked.

[Jay Shetty]

What would you draw?

[Jimmy Kimmel]

I draw my classmates, which they never liked. I would draw anything. Superheroes when I was a little kid, caricatures of people. I draw my family. I draw David Letterman on the television as I was watching him, pretty much. I still, to this day, if I have a pen and a piece of paper, I'll just scribble whoever is sitting in front of me as we're sitting there.

[Jay Shetty]

Wow. And so you'll still do it today?

[Jimmy Kimmel]

I do, yeah.

[Jay Shetty]

Have you done it on the show ever?

[Jimmy Kimmel]

Couple of times. It's hard to be funny and draw at the same time. They're like. They're totally different parts of your brain.

[Jay Shetty]

They definitely got that wrong. The media never gets anything wrong. Right.

[Jimmy Kimmel]

So, yeah. In this case, it's your fault. In this case, it's yours.

[Jay Shetty]

I'm always fascinated by what people wanted to be when they were growing up, and then what they end up becoming. Because I think there's so much hidden in childhood. And there's so many experiences, so many things we hear say the subjects we study at school. But you've had this history of pranks. Always being a central pillar. And for most of us, maybe you did a few pranks when you were a kid. How many of you did some pranks when you were kids? Any pranks? Yeah. All right. A few of you. I did a lot of pranks when I was kids. But sometimes you leave those behind. But you actually lost jobs because you did pranks on your colleagues. Yeah, bosses.

[Jimmy Kimmel]

Bosses.

[Jay Shetty]

Yeah, bosses. Right. All right.

[Jimmy Kimmel]

Is this gonna be where I crack open this Juni. And there's a cockroach in it or something like that?

[Jay Shetty]

Because you planted it. The sabotage.

[Jimmy Kimmel]

There's a prank. Yeah. I love pranks. I think the reason that I love pranks is because I grew up in a family that would scream and yell when I did something. And I got a great reaction out of it. I mean, really, if you don't want to be pranked, just don't react. That's the way to go. But I grew up. My Aunt Chippy is a very loud woman. She is on my show regularly. We are still. She's 85 years old. Most recently, I mean, I started by putting little explosives in her cigarettes and tying cans to the back of her car. And she would go to work, or she'd be in the casino in Las Vegas smoking, and pow. The cigarette would blow up, and then she'd call and curse me out over the phone. And I loved it. And now that I have a TV show, I'm able to escalate. So a couple of months ago. This has been a dream of mine since I saw those Waymo cars. She doesn't know about these. She lives in Las Vegas, and she's never seen a self driving car. So I had a guy pretend to be a chauffeur in a Waymo car, pick her up at the airport. He gets out of the car, he opens the door for her. He says, you mind? I have to use the restroom. And then we'll go. She's like, yeah, no problem. Go ahead. He closes the door of the car, and off it goes. And there was some real concern that this might kill her because she's 85. So I wrote to each of her daughters, my three cousins, I said, listen, this is what I'm planning to do to your mother. And I need your permission beforehand because I don't want to kill her on tv. And if I do, I need someone to blame. Within seconds, they all said, oh, definitely do it. Definitely do it. So we've got a sick family, but a fun family.

[Jay Shetty]

But talk to me about when you weren't. You didn't have the resources to pull it off your own show, and you were losing jobs over pranking your bosses. Like, first of all, where does the audacity come from? And second of all, how do you keep doing it? I believe it wasn't just once.

[Jimmy Kimmel]

I wouldn't call it audacity so much as I would call it stupidity. I thought that I was a dish jockey. I did a morning radio show, and I worked at a lot of radio stations in a lot of cities. If you've lived in a city, I've probably had a job and been fired in that city. And each time, I thought the bosses would be on board with the idea that the listeners would think it was funny if I was torturing them, because then they could drive to work and go, I love hearing these guys screw with their bosses. I wish I could do that, but I'm enjoying it through them. And they never liked it at all. They would tell me they were gonna like it when they hired me, and then when it happened, they hated it. Just dumb stuff. Once we were golfing, and I unlatched their golf bags on the back of the carts and then forgot about it for, like, six holes and then ran over their golf clubs. Once I completely smashed the inside of. I had a hot dog. It's a long story, but there was a hot dog that he didn't eat, and he threw in the garbage. And every night I would sneak in and put it in his drawer in his desk. And each day he'd open his desk, and there'd be a hot dog in there, and he didn't know why, and he'd throw in the garbage again. And then each time, I would get in there and I'd put it back in the desk. And then he started locking his office. So I climbed in over the. You know, the offices have that, like, kind of really cheap ceiling. I. I lowered myself in, and as I lowered myself completely, the desk collapsed. The shelves collapsed. It looked like the Northridge earthquake had happened. Only in his office. I knew that I'd be fired if he found out. So I just got out of there and locked the door, Put the hot dog in before I left and never mentioned it again. I don't know what he thought happened, but eventually they'd fire me. Eventually, they'd have enough of my Knowledge.

[Jay Shetty]

How did that conversation go, the firing? Was it a conversation or you just got a message like, what did that look like?

[Jimmy Kimmel]

Well, it would go like this. Now, of course, there were different situations, but generally it would go, so you know how you work here now, tomorrow you won't be working here, and in fact, we're gonna get a box, we're gonna go in your office, and we're gonna get all your shit, and we're gonna walk you out to the parking lot. I have to say, to this day, I hate firing people. It crushes me to fire somebody, even if they deserve it, even if they've done something bad, because I've been fired so many times. And it sounds funny. These stories are. I get that they're funny, but it wasn't funny at all at the time. You know, I was making like $18,000 a year and then had to go home and first of all, tell my wife at the time that I'd been fired again for being an idiot and that we're gonna have to pack all our stuff and move to tuc. And that happened over and over and over again until eventually I found a radio station here in la, kroq, that valued my commitment to nonsense. And I also grew up a little, and I learned, like, okay, don't call your boss's wife at home on the air and dig into their personal life, those kind of lessons, those important lessons that you learn along the way. And I was able to keep that job until I got a job in television.

[Jay Shetty]

I love your commitment to the prank.

[Jimmy Kimmel]

I have things going on right now that would blow your mind that I can't even talk about because they're bubbling. But what my thing is, my wife does not like. When I. My wife, I got her a. Did you know you can get a personalized license plate for anyone's car?

[Jay Shetty]

No. How does that work? Explain that to me.

[Jimmy Kimmel]

Well, what you do is you fill out the forms, and then you forge the person's signature at the bottom, and you write on the thing what you would like their personalized license plate to be. In my wife's case, I made it. We be jammin. And then the license plate came in the mail, and I went out in the garage and I screwed it onto the car, and I waited until she was. You know, until she came out to the car, and she wasn't happy. But I've done that with a lot of people. My band leader who plays the saxophone, I made one that says Senor Saxy, and I put that on his car. I got the idea at a U2 concert. Somebody had a license plate, said U2 fan. I thought, oh, okay, maybe I'll do that in a bad way.

[Jay Shetty]

What's a firing conversation that went wrong? What's the worst time you've fired someone and you're like, oh, I shouldn't have done it like that?

[Jimmy Kimmel]

Oh, well, one time it went on for like three and a half hours. It was me arguing and them crying and just kind of going around in circles over and over again until finally I was like, all right, I gotta go pick up my kids.

[Jay Shetty]

So wait, you fired them, then hugged them?

[Jimmy Kimmel]

Oh, yeah, right, yeah, there's always some hugging involved. Yeah, it's, you know, it's not great. I got fired one time and I'd been fired now so many times. I knew what was. I knew was coming. Because the way you know is they stop yelling at you. And once they stop yelling at you, you're in trouble. They're like, eh, forget, we don't need. Why bother? We're firing them in three weeks. But I went in and it was me and my partner on the radio and they sat us down, they said, listen, you know, we're gonna go in a different direction. And you know all that bullshit that they say to you, and this is probably best for you guys too. And I'm thinking, no, it's not. And then they gave the whole spiel and they were nervous and I said, listen, here's what we're gonna do. We're gonna come to work on Monday morning and we're gonna pretend like none of this ever happened. And there was a long moment of confused and terrified silence. And then I started laughing and gave him the finger and left, I think.

[Jay Shetty]

Before we dive into the next moment, let's hear from our sponsors. Apple gift Card is the perfect gift for back to school. Send it via email or send a physical card to your loved ones. Friends and family can use Apple gift Card to get products, accessories, apps, games, music, movies, TV shows and more. They can also spend it on in app content, music subscriptions and even iCloud. Plus. Visit ApplegiftCard Apple for details and to send Apple Gift Card this back to school season and back to our episode. On a serious note, what's beautiful about that is you were able to hold on to a really authentic part of self expression that was your comedy or something you found funny. It was something that you really believed was something everyone would find funny. You didn't give up on that. You were able to hold onto it and find A place, eventually that allows you to pull off these crazy things. How did you stay true to that when everyone's firing you, letting go of you, telling you this isn't a great idea. It's pushing people the wrong way. Like, how do you hold on to an idea when everyone's telling you it's terrible?

[Jimmy Kimmel]

Pure delusion. Just like a lot of the things I thought were so funny weren't even funny. They weren't funny. I wasn't that good at my job. And I think that's an important thing, too, because I look back at these jobs and I go, well, it wasn't all their fault. On one hand, I feel like maybe they should have recognized that I was always a very hard worker and that I did have some talent. I think every one of them would tell you that. But on the other hand, I was kind of crazy. I was doing antisocial things, and they didn't get it, and they didn't want to deal with it. They were adults, and I was this asshole, this kid, and they didn't want to deal with it. But I do have this thing where I just kind of figure like, well, if I think it's funny, then surely there will be other people that think it's funny, and it applies to other people, too. One of the best things about my job, and really about even when I was on the radio, is I've been able to identify and help other people who I saw as talented and who didn't quite know how to do it or make their way in or stay there once they got in. And that, to me, is very sad. Even just putting my Aunt Chippy on television, right? I'm not the first person to put one of their relatives on television, but I just kind of looked around and go like, well, I think she's funny. And so I think other people will think she's funny. And the same with my Uncle Frank, her ex husband, who was my security guard on the show before Guillermo was there, and then they were there at the same time. He was just this weird, very neurotic, very anxious former cop from New York who only arrested six people in 20 years and had this strange outlook on life where he would take $200 out of his ATM at the beginning of the week, and then he wanted to have $0 in his wallet at the end of the week, and it had to be that way. And so if he had any money left in his wallet on Sunday, he'd just give it to people like strangers. He'd just hand it out to people. And he was always doing this, like, weird stuff. And I, you know, one time, my band leader on my show is my best friend since I was nine years old. We grew up across the street from each other and I didn't know my relatives were funny until he thought they were funny. I was like, oh, they're annoying. They're always yelling at each other. It's like, oh, they're coming over. I said, my Aunt Chippy and Uncle Frank are coming over. He's like, oh, can I come? I was like, what? He's like, oh, they're hilarious. I was like, they are. And that clicked for me. I was like, oh, yeah, they are hilarious. And it turned out he was right. And I've just kind of operated by that principle for my whole life.

[Jay Shetty]

Yeah. Talking about family, you just became a granddad too, right?

[Jimmy Kimmel]

I did. My daughter Katie had a baby. A baby girl. Probably should have gotten more applause for that, but thank you.

[Jay Shetty]

I mean.

[Jimmy Kimmel]

I feel like almost killing my Aunt Chippy got more applause than having a. A granddaughter. But yeah, we're very excited. She's what, like maybe like eight days old or something? Yeah. Yes. Smoking already. Which we're concerned about.

[Jay Shetty]

But how does that feel? What is that like, psychologically, internally, mentally?

[Jimmy Kimmel]

I feel like, I don't know, people seem to think, like, first of all, people approach you cautiously in a way about it. Like, oh, so you're having like. Like, I'm going to be upset about this. What kind of an asshole would be upset about having a grandchild? But I guess people don't want to be thought of as old. And I don't really care that much about that. I'm just excited to have a little. And also being a grandparent, I think is going to be, first of all, an incredible way to get revenge on my children.

[Jay Shetty]

Tell me how, what are the pranks that are brewing?

[Jimmy Kimmel]

Not even pranks, just all the things they did to me that they're going to say, I know they're going to go, don't give. Please put them to bed before 11 o'. Clock. You know, don't give them a bunch of Reese's Pieces. And I'm gonna nod just like my parents do. And then I'm gonna do all the shit they don't want me to do. And I think that's one of the circle of life, you know, but it's fun and it's exciting and it's strange to see my daughter as a mom. I think that for me is the. It's not really about how I feel, because I've always felt like the same person. I feel like I'm the same person I was when I was nine years old. But to see, like, your daughter holding a baby and smiling is. It's. Yeah, people know. It's great.

[Jay Shetty]

Yeah, absolutely. Give it up. It's. It's beautiful to hear about that because, yeah, it's. I've. I have no experience at all.

[Jimmy Kimmel]

You have no grandchildren.

[Jay Shetty]

I don't have kids, no grandkids. And it's really fascinating watching someone you love grow into becoming someone else. Like you said, it was strange watching her do it. What are you noticing in her that feels that way?

[Jimmy Kimmel]

Well, she's breastfeeding, which she'd never done before. You know, she's. Seeing my daughter is very funny. All my kids are really funny. My daughter Katie is very funny. She's got a very strange sense of humor. She's an artist. She makes these funny ceramics. Her name is Katie Kimmel. You could see her on Instagram, and she. You will get. You will understand what I'm talking about. She does. Like, today, she sent me, like, I sent her a text this morning, and I said, you're not posting enough pictures of the baby on the stream. And so she just posted a bunch of pictures of the baby screaming and crying. And the baby's wearing a onesie that says, I'm 11 years old. So I know she's gonna. You know, she's not gonna be a traditional mom, but just seeing her be a mom is. It's just funny. I think it's like anything. Like, when I try to remember how old I am. I don't know if you ever forget how old you are. Yeah, I have to remember how old my sister is and add three years. That's how I get to it. And just seeing my kids become adults and both of my older kids are married and having to pay rent and be a husband and a wife is weird. It's just weird. You know, it's great, but it's weird.

[Jay Shetty]

Yeah. They obviously inherited your comedic gene, it sounds like.

[Jimmy Kimmel]

Yeah. I wouldn't necessarily classify it as genius, but they are very funny and just very good people. I think more importantly. No, funny's more important. Let me rank it. Hold on a second. Yeah, funny. Definitely more important than good, but both important. Super important. Yeah.

[Jay Shetty]

What's a part of you that you didn't want them to inherit?

[Jimmy Kimmel]

My nose. I didn't want my daughter to have my beard, for sure. My anxiety, maybe. Of course, you know, kids, they inherit that. Whether you want them to or not? But I think anxiety, yeah. And I think, like, growing up without any money adds a measure of anxiety. But then you realize, like, you know, my older kids, I didn't have any money when they were growing up, but now my younger kids, I do. It's interesting because they somehow managed to get to the anxiety. Like, they find different paths to it. It has nothing, it turns out, it doesn't. Like, for me, like, when I was a kid and I loved to draw, I told you I would get, like, a set of pens for Christmas, and I would never want to use them because if I used them, they'd run out. And so I'd have these pens that I never used, and eventually they'd just dry out because we lived in Las Vegas and. What a terrible thing. So now, you know what I do? I buy a million art supplies, and the house is like a dick blick, you know, my house is just full of these art supplies. And I know that I will never. I will not live long enough to use all this stuff. But knowing it's there makes me feel like I've conquered that anxiety in some way.

[Jay Shetty]

By hoarding.

[Jimmy Kimmel]

By hoarding.

[Jay Shetty]

So the reason why anyone else can't get art supplies is Jimmy Kimmel.

[Jimmy Kimmel]

That's right, yes.

[Jay Shetty]

Walk me through what anxiety really feels like at this point now in your life. How your relationship with it's changed over that time. From going from being anxious about not having money, not having resources, not having a job. What does that look like as the externals change? What happens on the inside?

[Jimmy Kimmel]

Well, it's a lot simpler when you don't have any money because the things you're thinking about are, you know, do I have enough cash in my checking account to have lunch today to get a twenty dollar bill out? And like, it's like, oh, I have $21.18. Great. You know, and that's significant, certainly. But then you get in a. You wind up in a position where a lot of people rely on you for a lot of things. And, you know, people will come to you with very serious needs, serious requests. Your relationship with people changes. It's hard to navigate that. It's hard to even find people to talk about it with. There are, as far as I know, no books on how to handle it. And you wind up having these kind of, like, intimate conversations with famous people. You don't even really know that well. I mean, like, I know a guy who is a real, like, family guy, who's a very wealthy guy. He's a very Famous actor. And I said, how many houses have you bought for your family? And he thought about her for a second, and he goes, 17. That was my reaction, too. And you can't be the nephew anymore at that point. You're the person that people go to when they need something. And it can be a lot, you know? It really can. I mean, I shouldn't complain. Now I sound like I'm complaining. Oh, Jesus. We all have problems, right? I mean, some of them are just different than others.

[Jay Shetty]

Yeah. What do you do about that anxiety? What do you do with it? Just buy more houses?

[Jimmy Kimmel]

For the most part. Yeah. Yeah, yeah, yeah. It depends, you know, But I'm hopefully getting better about it, you know, because it's hard to explain to people when they want money, but your relationship with them is more important than that money. And then sometimes you realize, like, oh, wait, their relationship with me is not more important than the money. And that's when you have to reevaluate the relationship.

[Jay Shetty]

That's tough.

[Jimmy Kimmel]

Yeah, it's hard.

[Jay Shetty]

That's. That's really, really tough. I mean. Yeah. Is there someone particular or someone specific that you think about when you. When you share that?

[Jimmy Kimmel]

My wife, she's sucking me dry. Jay. How much do I get for this?

[Jay Shetty]

Do I get paid?

[Jimmy Kimmel]

No, nothing.

[Jay Shetty]

Shit, no. She made you do this for free?

[Jimmy Kimmel]

No, there's no one in particular. It just. It comes up, you know? It happens.

[Jay Shetty]

Yeah. In my small journey with it, I've definitely experienced that as well. Losing people that you thought you were close to. Yeah. Realizing what standard or frequency of relationship you had with someone, you put them up here and you thought you had this bond, and actually you realize it was just based on finances or access or whatever it may be.

[Jimmy Kimmel]

Yeah. Sometimes you get an email from somebody you went to the sixth grade with asking for a huge amount of money for something nonsensical.

[Jay Shetty]

It's not even for a charity. It's like, never.

[Jimmy Kimmel]

Never.

[Jay Shetty]

It's crazy. Any crazy requests you can share, you know?

[Jimmy Kimmel]

Yeah, I've had a lot of crazy requests. I mean, you know, people think you can wave a magic wand and make all their problems go away, and it's not true. You know, even if a lot of times you give them what they want, they still have to deal with whatever got them there in the first place. So, you know, trying to keep that in mind, I think is important. But these are not the kinds of things that occur to people when they're in a pinch.

[Jay Shetty]

Yeah, absolutely. You've been talking about your wife a lot tonight. And how long have you been together now?

[Jimmy Kimmel]

We are celebrating our 12th anniversary in July. We've been together, I don't know, like 16 years or something like that.

[Jay Shetty]

That's beautiful. And I believe you met on the show.

[Jimmy Kimmel]

I did, yes, we met on the show. My wife is the executive producer, one of the executive producers of the show. And we made love and I asked her.

[Jay Shetty]

So it wasn't you and your guest?

[Jimmy Kimmel]

It was, yeah, I got right to it. Yeah. No, she was not a guest. No, wasn't like us.

[Jay Shetty]

Yeah, it wasn't like us. Bit different. Yeah. This is terrible. This is terrible.

[Jimmy Kimmel]

It won't be that bad. I'm very gentle.

[Jay Shetty]

This is all my. This is. This is what all my British friends worry about LA being like. This is what they all worry about.

[Jimmy Kimmel]

Yo. You mean all the friends who got buggered in boarding school are worried about?

[Jay Shetty]

No, they're all like, what are all the parties in LA like? And you know they're gonna be like, what's Jimmy Kimmel actually like? And I'm gonna have to show them this.

[Jimmy Kimmel]

Yeah, let them know, invite them over.

[Jay Shetty]

Apart from the pranks, what have been the. There's a lot of people out here either looking for love who are still searching. You know, everyone always says it's always hard to date in la.

[Jimmy Kimmel]

Yeah.

[Jay Shetty]

Is that true?

[Jimmy Kimmel]

I think it is. I mean, I've never really been in that position. I've gone from one long term relationship to another, but certainly people close to me and my life, I've seen them have a really hard time and even like, think like, oh, maybe I should move back to Chicago on that kind of thing. And I go, but wait a minute. But there's. There's just people here and there, whatever. And obviously the apps have changed that a lot. Sometimes for the better, sometimes for the worse, I guess, depending what your intentions are. But, yeah, sometimes I feel bad for people because it does seem to be hard.

[Jay Shetty]

Yeah. What's been the secret for your connection? What's been the secret source to the 16 years and the 12 years of marriage?

[Jimmy Kimmel]

Left to my own devices, I'm not great. Okay. But my wife is very good. She will say she wants to. I'm just checking in with you. And I'm like, what is this checking in? She probably learned it from you.

[Jay Shetty]

Just checking in. Yeah, that sounds about right. There's four check ins, there's one every week, one every month, one every quarter, and one every year.

[Jimmy Kimmel]

And I get nervous. I'm like, well, what are you checking in about? Like, what what am I, a motel? She's like, no, just. How are you? How you doing? I'm like, oh, I'm fine. What did you hear? I don't know. I have a very. I have tunnel vision, you know, Like, I got stuff I need to get done, and I want to get it done. And sometimes I forget there are other human beings around me that, you know, would like to check in from time to time. So I've learned a lot, and I'm still not great at it, but I am better at it than I was. And I feel like I've matured a lot thanks to my wife. And in what way? In what way have I matured? Oh, Jesus Christ.

[Jay Shetty]

You don't get away with saying a statement.

[Jimmy Kimmel]

I knew you would do this, Jay. I knew it. I knew coming in here. What ways have I matured? Now when we hold hands, I don't take hers and put it behind me and fart on it anymore. And that's a big step for me. All right, let me get serious here. It's hard. I make jokes when I'm confronted with a serious situation. No, don't ask her. I don't know if she wants to be asked. Oh, she's standing. She wants to be asked.

[Jay Shetty]

I need a mic.

[Jimmy Kimmel]

All right. Before she gets up here, Jay. I should just say I haven't matured. I was lying. I just wanted to sound. I wanted to fit in with the podcast. Oh, this is what it was. Yeah. Right. Hi. Sit on my lap. Yeah.

[C]

Not gonna sit on your lap. I'm not gonna sit on your lap. He gets uncomfortable when we talk about serious things. He's definitely maturing in that area.

[Jimmy Kimmel]

Oh, I don't see any evidence of that.

[C]

I'd like to say, first of all, I'm very proud of you coming here and being here.

[Jimmy Kimmel]

Oh, thank you.

[C]

Because I think that's mature of you.

[Jimmy Kimmel]

Oh, see, okay, there's that.

[C]

Jimmy is incredibly self deprecating if you can't tell, and that's his defense, which is beautiful and wonderful and we all get to enjoy it. But I get to tell people how wonderful you are, and I love to do that. And I think one of the things, the most beautiful things you've done in evolving as a human is sharing your story regularly on the show. Fighting for healthcare, for children, fighting for people. I think maybe you went from being a little more inward to outward over the last decade of your life, and I think it's been beautiful to witness.

[Jimmy Kimmel]

Well, thank you for bringing it out of me.

[C]

You're welcome.

[Jimmy Kimmel]

Thank you.

[Jay Shetty]

All right.

[C]

You have a lot of more work to do, though, so I'll just.

[Jay Shetty]

Jimmy. Jimmy, now it's your turn. We need, you know. Yeah, Jimmy, turn this into a session.

[C]

Yeah.

[Jay Shetty]

Okay. Now it's your turn. Please.

[Jimmy Kimmel]

Well, first of all, is it just me, or does it suddenly smell like toast?

[C]

It does.

[Jay Shetty]

It does.

[C]

You're having a stroke. He's having a stroke.

[Jay Shetty]

It does.

[C]

Okay.

[Jimmy Kimmel]

Oh, wouldn't you love that? Yeah. Well, yeah. You know, I'm always amazed at how easily these kind words come out of my wife. And not just for me, but for others. Like, there's nobody you'd rather have give a toast at your birthday dinner. Because she really speaks from the heart and speaks very beautifully and makes people feel really good, and I don't think there's any better quality than that.

[C]

Thank you. I love you. And I love you.

[Jay Shetty]

I love you, too, Molly. Thank you so much. You're welcome.

[C]

Your eyes really are beautiful.

[Jimmy Kimmel]

More. Well.

[C]

We'Ll see how the night goes. No, I love your wife, too.

[Jay Shetty]

All right, give it up for Molly, everyone.

[Jimmy Kimmel]

Thank you, Molly.

[Jay Shetty]

Thank you.

[Jimmy Kimmel]

Oh, you really put me on the spot there, Jay.

[Jay Shetty]

Whoa. She saved you.

[Jimmy Kimmel]

She saved me.

[Jay Shetty]

She saved you. I mean, you know, I put you on the spot, but she saved.

[Jimmy Kimmel]

You're right.

[Jay Shetty]

Okay, so now we're going from couples therapy to individual therapy.

[Jimmy Kimmel]

Oh, okay, Great.

[Jay Shetty]

Has talking about your emotions always been something that you found challenging?

[Jimmy Kimmel]

Yes.

[Jay Shetty]

Not useful. Like where on that spectrum? Talk. Talk to me about that. What? What spectrum? Is it like, what does that look like? Like.

[Jimmy Kimmel]

Well, I think my dad's the same way because I hear my mother yelling at him about it. But, yeah, it's very. You know, I can write a nice letter. I'm good with that. But there's something about expressing myself in a very honest way that is difficult for me. Why is it?

[Jay Shetty]

The answer's within. The answer's not within. It's within only you can.

[Jimmy Kimmel]

There's a lot of stuff in there.

[Jay Shetty]

Yeah.

[Jimmy Kimmel]

I'm not sure I want to go rummaging around. There's a whole pizza in there.

[Jay Shetty]

But first, here's a quick word from the brands that support the show. This episode of On Purpose is brought to you by Chase Sapphire Reserve. I believe that travel is one of the greatest gifts that we've ever been given, and Chase Sapphire Reserve has been my gateway to the world's most captivating destinations. When I use my Chase Sapphire Reserve card, I get eight times the points on all the purchases I make through Chase Travel and even Access to one of a kind experiences. Experiences like music festivals and sporting events. And that's not even mentioning how the card gets me into the Sapphire Lounge by the club. At select airports nationwide. Travel is more rewarding with Chase Sapphire Reserve. Trust me. Discover [e-mail] Sapphire Reserve cards issued by JP Morgan, Chase Bank, NA Member, FDIC, subject to credit approval terms apply. All right, thank you to our sponsors. Now let's dive back in. When was the last time you felt like you accessed that part without a letter and you were able to share that part of yourself?

[Jimmy Kimmel]

About 86 seconds ago?

[Jay Shetty]

No, but your emotions, Your emotions, not about someone else, but how you feel.

[Jimmy Kimmel]

About something about someone else?

[Jay Shetty]

Well, no, no, not how you feel about someone else. How you feel about your own emotions or feeling an emotion that may be uncomfortable or difficult or challenging. When was the last time you feel you did do that?

[Jimmy Kimmel]

With our therapist? Last Friday at 9:18am it's easier with the therapist. You know, I was listening to you with Bert Kreischer. You had him on your podcast and he said something. He said that after, after he and his wife go to therapy, he declares a winner.

[Jay Shetty]

Do you do the same thing?

[Jimmy Kimmel]

No, but I like that a lot.

[Jay Shetty]

Who wins?

[Jimmy Kimmel]

You know, I don't think anybody wins, really. No, I think it's just helpful. I think it's really a good thing. I find it very uncomfortable, but I'm never not glad that I did it afterwards. I think it's just a good thing to talk. I mean, maybe it's the reason why we can talk as humans because we're supposed to. And I think it's good. And I think a lot of guys don't like to go to therapy and then they're looking for somebody who's gonna be on their side and they're looking for a referee more than a therapist. And that's probably not the way to go in it. I will say from my own personal experience that I recommend it both individually and together. And I think that it's helped me a lot in my life to sort things out, you know, And I think what you do is, you know, is very helpful for people because, I mean, obviously, you know, there are a lot of people here just trying to figure out who they are and how to go about their lives and how to be happy. And it's hard. It's hard to figure out to be happy. I mean, there's. There's no logical reason why we should, should be happy. It doesn't make sense. There are so many people suffering and there's so many sad and bad things happening, and it feels selfish sometimes to be happy. It was like, oh, yeah, great. Things are going great for you, but look what's, you know, kids don't have lunch. And I think that it takes a lot to, to remember that that's not good for you and it's not helping anybody. And if you really want to do something, do something. Don't just worry about it. And so that's something that I think is important. And I also found that, like, you know, sometimes people want advice and sometimes I want advice. And sometimes people who are asking for advice don't really want to. They don't want advice. They just want something. And I always think that when you're really down, when you're feeling low, and when you're looking for answers, helping other people is always a help. It always makes you feel better. So if there's a situation where you're feeling worthless or you're feeling unloved or whatever, the best thing you can do is to help someone else. And for yourself, not even for them. It's almost a selfish thing to do. And I think it always works.

[Jay Shetty]

I agree. I love that. I love that. Jimmy, you've been amazing. Tonight we end every on purpose interview with the final five. These questions have to be answered in one word to one sentence maximum. So, Jimmy Kimmel, these are your final five. The first question is, what is the best advice you've ever heard or received?

[Jimmy Kimmel]

Well, it's not be yourself. We learned that earlier. Listen, listen. That's the best advice.

[Jay Shetty]

Who did you hear that from?

[Jimmy Kimmel]

I heard it from a priest. Yeah. A friend of mine who's a priest. Yeah. I said, what do you do when people come to you and they say, you know, my son is dying and I don't believe in God? He said, I just listened to them. Good advice.

[Jay Shetty]

Speaking about that, you've been very open about your son's heart condition.

[Jimmy Kimmel]

Yeah.

[Jay Shetty]

And that's been something that I imagine is extremely difficult.

[Jimmy Kimmel]

Well, not anymore because he's, he's doing great. But it was. Yeah. For sure. Yeah.

[Jay Shetty]

What, what helped you at that time? What, what helps you in. In such a difficult, dire situation?

[Jimmy Kimmel]

And, well, number one Children's hospital here in Los Angeles helped me. The support, the support from family and strangers. And I'm a religious person. I grew up going to church, Catholic and all those things. But. And I think that the thoughts and prayers, that gets thrown around a lot people, when they say they pray for you, that's to take a moment of your day to stop and think about someone else and their child. It's a. It's a small sacrifice, but it's a meaningful one. Whether you believe in prayer or not, I just think it's powerful and meaningful. And I know that's more than one sentence, but that's the answer.

[Jay Shetty]

Thank you, Junior. Thank you so much. That was actually just question number one. I, I just snuck another one in there.

[Jimmy Kimmel]

Oh, no.

[Jay Shetty]

Question number two. What is the worst advice you ever heard or received?

[Jimmy Kimmel]

You know, I don't really have an answer to that. I think that the worst thing you can do and I've done it, and it's something that I've learned, is to lash out. You gotta take a beat and think about what you're saying because you'll wish you had. So sometimes there are people that just want you to bring down the hammer of Thor. And that's not usually the way I go.

[Jay Shetty]

I like that. All right, question number three. What's the first thing you do in the morning and the last thing you do at night?

[Jimmy Kimmel]

Brush my teeth. You mean besides pee? I guess. Yeah. You know, we have, you know, we have an 8 year old and a 10 year old in the house. So he comes and our 8 year old and pounces on us in the morning. And I just like to snuggle with him. And then he wants us to come to bed with him at night and put him asleep every night. And we know that we shouldn't do it every night, but we just want to. And we want to get in there with him. And most of the time we're very easy to convince. So those are the, you know, the best. In the morning with the kids in the bed and then again again at night with the kids in the bed.

[Jay Shetty]

I love that. All right, last two questions. Question number four. What's something that you used to value that you no longer value?

[Jimmy Kimmel]

My parents. No, No, I love my parents. You know what? I don't drink much anymore. I. I used to, you know, I was never. I never like, had a problem or anything like that, but I just. It's less interesting to me now.

[Jay Shetty]

Why? Why is that?

[Jimmy Kimmel]

Because I'm so high all the time. We call that California Sober, I believe.

[Jay Shetty]

Yeah. All right, fifth. Fifth and final question. We ask this to every guest who's ever been on the show. If you could create one law that everyone in the world had to follow, what would it be?

[Jimmy Kimmel]

It's the golden rule. Do unto others. That's it. That's the whole thing that's all you. If we all did that, we'd be doing great. Yeah.

[Jay Shetty]

Jimmy, we've got one special segment to wrap it up for you.

[Jimmy Kimmel]

Okay.

[Jay Shetty]

I want to show you something behind you. If we can get the first one up. Take a look.

[Jimmy Kimmel]

That's me.

[Jay Shetty]

What advice would you give to your younger self? To that self? That younger self.

[Jimmy Kimmel]

To young Jimmy Kimmel in the seventh grade. Play the saxophone instead of the clarinet. You're never getting laid.

[Jay Shetty]

I love it. Can we get a second up? Looking very dapper. What does Jimmy Kimmel need to hear right now?

[Jimmy Kimmel]

Get away from that young boy.

[Jay Shetty]

You mean me, right?

[Jimmy Kimmel]

Both of you.

[Jay Shetty]

And then let's get the last one, courtesy of my team.

[Jimmy Kimmel]

You know, honestly, I never even thought I'd own a suit. So I'm ahead of the game right now, I think. Was that AI Me in the future?

[Jay Shetty]

Yes.

[Jimmy Kimmel]

Why is my beard the same color as it is now?

[Jay Shetty]

You're aging well. You're aging well. What do you. What do you hope you'll feel about yourself at that age?

[Jimmy Kimmel]

I hope I don't look like that number one. I do hope I have that much hair. I have a feeling I am going to be replaced by an AI Me at some point in the future. I hope I wind up like my grandfather. And by that, I don't mean dead. I mean just somebody that everybody thinks of and loves.

[Jay Shetty]

Give it up for Jimmy Kimmel, everyone. Thank you so much.

[Jimmy Kimmel]

Thanks, Jay.

[Jay Shetty]

If you love this episode, I need you to listen to one of my favorite conversations ever. It's with the one and only Tom Holland on how to overcome your social anxiety, especially in situations where you're not drinking and everyone else is. We talk about his sobriety journey and so much more. He gets really personal. I can't wait for you to hear it. It's gonna blow your mind.

[Jimmy Kimmel]

The quote is, if you have a.

[Jay Shetty]

Problem with me, text me. And if you don't have my number, you don't know me well enough to have a problem with me. Gatorade zero. The number one proven electrolyte blend made with zero sugar, designed to hydrate better than water so you can lose more sweat and push more limits. Gatorade zero. Is it in you? This is an I heart podcast.