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

25:22You know, 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 now i'm not i'm not the first person to put one of their relatives on television but i just kind of looked around i 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.

26:06He 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 just hand it out to people. And he was always doing this like weird stuff. And I, you know, at 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.

26:49And 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. They're, you know, it's like, oh, they're coming over. He's, I said, my aunt Chippy and Uncle Frank 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. Yeah. Talking about family, you just became a granddad too, right? I did.

27:21My daughter, Katie, had a baby, a baby girl. Probably should have gotten more applause for that.

27:31Thank you. I feel like almost killing my Aunt Chippy got more applause than having a granddaughter. But yeah, we're very excited. She's what, like, maybe like eight days old or something. Yeah. Yeah. Smoking already, which we're concerned about. How does that feel? What is that like psychologically, internally, mentally? I feel like, I don't know. people seem to think like i first of all people approach you cautiously in a way about it like oh so you're having like like i'm gonna be upset about this like 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 tell me how what are the pranks that are brewing not even pranks just all the things they did to me that they're gonna say i know they're gonna 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 We're the circle of life, you know?

28:55But it's fun, and it's exciting, and it's strange to see my daughter as a mom. I think that for me, 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 your daughter holding a baby and smiling, people know it's great. Yeah, absolutely. Give it up. it's um it's beautiful to hear about that because yeah it's uh i've i have no experience you have no grandchildren i don't have kids no grandkids and it's it's really fascinating watching someone you love grow into becoming someone else like you said it was strange watching her do it what what are you noticing in her that's that feels that way well she's breastfeeding which she'd never done before you know she's um she's seeing my daughter is very funny my 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 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.

30:16And 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.

30:27So I know she's not going to be a traditional mom, but just seeing her be a mom is 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. 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 yeah they they obviously inherited your comedic gene it sounds like i yeah i don't i don't i wouldn't necessarily classify it as genius but they are very funny and they're just very good people i think more important no funny's more important they're let me rank it hold on a second yeah funny definitely more important than good but both important super important yeah what's a part of you that you didn't want them to inherit my nose

31:39I 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 and 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 use them, they'd run out.

32:24And so I'd have these pens that I never used and eventually they 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. My house is just full of these art supplies and I know that 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. By hoarding. By hoarding. So the reason why anyone else can't get art supplies is Jimmy Kimmel. That's right. Yes. 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.

33:16What does that look like as the externals change? What happens on the inside? 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$20 bill out. And like, it's like, Oh, I have$21 and 18 cents. 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 people will come to you with very serious needs, serious requests, your relationship with people changes. It's hard to navigate that.

34:00It'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.

34:45It 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 yeah what do you do about that anxiety what do you do with it just buy more houses for the most part yeah yeah yeah yeah it depends you know but um I'm hopefully getting uh 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.

35:22And that's when you have to re-evaluate the relationship. That's tough. Yeah, it's hard. That's really, really tough. I mean, yeah. Is there someone particular or someone specific that you think about when you share that? My wife. She's sucking me dry, Jay. How much do I get for this? Do I get paid? No, nothing. No, shit. No, she made you do this for free. No, there's no one in particular. It just, it comes up, you know, it happens. 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.

36:03And 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. Yeah. And that happens very quickly. You get an email from somebody you went to the sixth grade with asking for a huge amount of money for something nonsensical. It's not even for a charity. No, never. Never. It's crazy. Any crazy requests you can share? You know, 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.

36:44So, 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. Yeah, absolutely. You've been talking about your wife a lot tonight. And how long have you been together now? We are celebrating our 12th anniversary in July. We've been together, I don't know, like 16 years or something like that. That's beautiful. And I believe you met on the show? 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 to marry me. So it wasn't you and your guest.

37:23It was, yeah. I got right to it. Yeah, no. She was not a guest, no. It wasn't like us. Yeah, it wasn't like us. A bit different, yeah. This is terrible. This is terrible. It won't be that bad. I'm very gentle. This is what all my British friends worry about L.A. being like. This is what they all worry about. You mean all the friends who got buggered in boarding school are worried about? No, they're all like, what are all the parties in L.A. like? And they're going to be like, what's Jimmy Kimmel actually like? And I'm going to have to show them this. Yeah. Let them know. Invite them over. apart from the pranks what have been the there's a lot of people out here either looking for love who've we're still searching you know everyone always says it's always hard to date in LA yeah is that true 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 have I've seen them have a really hard time and even like think like, well, maybe I should move back to Chicago and that kind of thing.

38:34And I go, well, 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 on what your intentions are. But yeah, sometimes I feel bad for people because it does seem to be hard. Yeah. What's been the secret for your years and the 12 years of marriage? Left to my own devices, I'm not great. Okay. But my wife is very good. She will say, um, 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.

39:16So keep just checking in. That sounds about right. 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. And I get nervous. I'm like, well, what are you checking in about like what what am i a motel it'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 that there are other human beings around me that 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.

40:02And I feel like I've matured a lot thanks to my wife. In what way? In what way have I matured? Oh, Jesus Christ. You don't get away with saying a statement right down the bush. I knew you would do this, Jay. I knew it. I knew coming in here. what ways have I matured

40:25now 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 alright let me get serious here it's hard I make jokes when I'm confronted with a serious situation

40:47no don't ask her I don't know if she wants to be asked oh she's standing she wants to be asked

41:00I need a mic alright before she gets up here Jay I should just say I haven't matured I was lying

41:09I just wanted to sound I wanted to fit in with the podcast oh this is what it was yeah right i sit on my lap yeah i'm not gonna sit on your lap i'm not gonna sit on your lap um he gets uncomfortable when we talk about serious things he's definitely maturing in that area i don't see any evidence of that i'd like to say first of all i'm very proud of you coming here and being here oh thank you because I think that's mature of you oh see okay there's that 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 and evolving as a human is sharing your story regularly on the show fighting for health care 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 well thank you for bringing it out of me you're welcome thank you you have a lot more work to do though Jimmy, Jimmy, now it's your turn we need to turn this into a session Yeah.

42:38Okay. Now it's your turn. Please. Well, first of all, is it just me or does it suddenly smell like toast? It does. It does. You're having a stroke. He's having a stroke. It does. Okay. Oh, wouldn't you love that?

42:57Well, 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 you, 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 is makes people feel really good. And I don't think there's any better quality than that. Thank you. I love you. And I love you. I love you too, Molly. Thank you so much. You're welcome. Which one of us do you love more? Well, we'll see how the night goes. I love your wife too give it up for Molly everyone thank you Molly thank you oh you really put me on the spot there Jay whoa she saved you she saved me I mean you know I put you on the spot yeah no you're right so now we're going from couples therapy to individual therapy oh okay great has talking about your emotions always been something that you found challenging yes 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 well I think my dad's the same way because I hear my mother yelling at him about it but um 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 uh is difficult for me why is it

44:35the answer's within the answer's not within here yeah only only you can there's a lot of stuff in there yeah i'm not sure i want to go rummaging around do you there's a whole pizza in there 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. Every time I travel, I find a part of myself I didn't know was missing. I remember being in this small town, completely unplugged, and for the first time in a while, I felt still.

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47:18Okay, I'm going to assume that everybody messages their friends. I'm also going to assume you've run into some issues when messaging, especially during group chats. I know I have. One time I sent a message way too fast, full of typos, and everyone had to guess what I was even trying to say. WhatsApp can help. First, you can message privately with everyone, even if you're all using totally different phones. It just works. Sent a message too fast and instantly regretted it? No problem, just edit it. And when the chat gets a little too intense, you can switch to a group video call and actually talk it out.

47:55Photos and videos come through super clear and messages get delivered without weird gaps or delays. Plus, WhatsApp has so many great features like polls, pinned messages and even event invites with rsvps so planning stuff doesn't just turn into a mess i mean it just makes a lot of sense it's time for whatsapp message privately with everyone 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 about 86 seconds ago. No, but your emotions, your emotions, not about someone else, but how you feel about something.

48:38About someone else. 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? With our therapist last Friday at 9.18 a.m. It's easier with the therapist. You know, I was listening to you with Bert Kreischer. Yeah. You had him on your podcast? Yeah. And he said something. He said that after he and his wife go to therapy, he declares a winner.

49:17Do you do the same thing? No, but I like that a lot. who wins you know we 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 i'm never not glad i i that i did it afterwards i 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 going to 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.

50:01I 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 no logical reason why we should be happy. It doesn't make sense. There are so many people suffering and there's so many sad and bad things happening.

50:44And it feels selfish sometimes to be happy. It's 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 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.

51:24And 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. because, and for yourself, not even for them. It's almost a selfish thing to do. And I think it always works. I agree. I love that. I love that.

52:05Jimmy, 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? Well, it's not be yourself. We learned that earlier.

52:28Listen, listen, that's the best advice. Who did you hear that from? 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. But he said, I just listened to them. Good advice. Speaking about that, you've been very open about your son's heart condition. Yeah. And that's been something that I imagine is extremely difficult. Well, not anymore because he's doing great. But it was, yeah, for sure. What helped you at that time? What helps you in such a difficult, dire situation?

53:13Well, number one, Children's Hospital here in Los Angeles helped me.

53:22The support, the support from family and strangers.

53:34And I'm a religious person. I grew up going to church, Catholic and all those things. 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.

54:04It'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. Thank you, Jimmy. Thank you so much.

54:29That was actually just question number one. I just snuck another one in there. Oh, no. Question number two, what is the worst advice you ever heard or received? 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 got to take a beat and think about what you're saying because you'll wish you had. Yeah. So sometimes there are people that, you know, just want you to bring down the hammer of Thor. And, um, that's, that's not usually the way I go. I like that. All right. Question number three.

55:15What's the first thing you do in the morning and the last thing you do at night? Oh, brush my teeth. Well, you mean besides pee? I guess. Uh, yeah. You know, we have an 8-year-old and a 10-year-old in the house. So he comes, 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 to sleep 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. And so those are the, you know, the best in the morning with the kids in the bed.

55:55And then again at night with the kids in the bed. I love that. All right. Last two questions. Question number four. What's something that you used to value that you no longer value? My parents. No, I love my parents.

56:17You know what? I don't drink much anymore. I used to, you know, I never had a problem or anything like that, but it's less interesting to me now. Why is that? Because I'm so high all the time.

56:35We call that California sober, I believe. All right, fifth and final question. We ask this to every guest who's ever been on the show. So if you could create one law that everyone in the world had to follow, what would it be? It's the golden rule. Do unto others. That's it. That's the whole thing. That's all. If we all did that, we'd be doing great. Yeah. Yeah. Jimmy, we've got one special segment to wrap it up for you. Okay. I want to show you something behind you, if we can get the first one up. take a look that's me what advice would you give to your younger self to that self, that younger self to young Jimmy Kimmel in the 7th grade play the saxophone instead of the clarinet you're never getting laid

57:33I love it can we get a second up looking very dapper what does Jimmy Kimmel need to hear right now Get away from that young boy. You mean me, right? Both of you. And then let's get the last one courtesy of my team. 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? Yes. Why is my beard the same color as it is now? You're aging well. You're aging well. What do you hope you'll feel about yourself at that age? 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 A.I.

58:30me at some point in the future. I hope I wind up like my grandfather. And by that, I don't mean dead. I mean, it's just somebody that everybody thinks of and loves. Give it up for Jimmy Kimmel, everyone. The best. Thank you so much. Thanks, Jay. 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 going to blow your mind.

59:10The quote is, if you have a 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. 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.

59:45And 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 more at chase.com forward slash sapphire reserve. Cards issued by JPMorgan Chase Bank, NA. Member FDIC. Subject to credit approval. Terms apply. This is Jay Shetty from On Purpose. If you've ever felt off balance, sometimes a change of scenery is the best reset. Delta invited four creators to explore one idea. What if travel isn't just movement, but recharging in motion? And the results? Based on their Oura Ring sleep scores, everyone met the day feeling more rested.

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