EP. 80 — Conan O’Brien

Jameela: [00:00:00] Hello and welcome to another episode of I Weigh with Jameela Jamil. I hope you’re well, I uh, in spite of everything that’s going on in the world right now, I’m quite good today only because I got to talk to someone that I am not I’m quite in love with him. I’m a little bit in love with him. James knows he’s fine with it. He’s also in love with him. It’s it’s a whole thing. It’s an ongoing whole thing. But I he’s just I just, oh, he’s my hero and I love him and I’m in love with. It’s complicated. But his name is Conan O’Brien. I’ve got Conan O’ bloody Brien on my podcast. What else do I need to achieve in life? I’m flicking my hair. This is the sound of me flicking my hair because I’m so happy that I managed to get someone that I’ve been watching on telly since I was a kid. And I just I have been obsessed with him for such a long time. I just love him so much. I just want to want to make people as happy as he makes people and wish that my brain could work the way that his does. He’s my favorite person to be interviewed by by a country mile, and I’m so thrilled and honored that he was here today to have such a fun and personal conversation with me. You know, because he’s an interviewer it’s very rare that we got to really hear much about Conan himself. Not everyone’s like me where they crowbar their personal information into all of their interviews with other people. Like just keep trying to involve themselves in other people’s stories. I hope you don’t mind that I do that. I’m really sorry if you do, I’ll try and keep an eye on it. But Conan doesn’t do that. He really makes it about the guest. That’s why he’s such an iconic interviewer. And so it was really fun to learn more about Conan and to learn about Conan O’Brien’s fears. What the fuck could Conan O’Brien fear? We talk about his mental health, his journey with anxiety and how it runs in his family, and we talk about therapies that have helped him. We talk about the root cause of his depression. We also talk about both of our asses. You know, we talk about his ass. We talk about my ass. We we talk about our feelings about our asses. Not each others. There are some mild but very tongue in cheek flirting, so I’ll just offer a warning for that. If you want to hear two very embarrassing, awkward people do bad, performative flirting at each other, whilst both in extremely happy relationships that we totally don’t mean anything we’re saying, then just be prepared. And I talk to him about, you know, gaining happiness with age, which I think is something that we all hopefully strive towards. Hopefully, after the last year and a half, we’re not looking at aging as an embarrassing thing. I’ve really I really hope that we look at it as a great privilege, and it’s wonderful to see him in real time, get happier and happier with every year. And while I know he’s not probably the most traditional guest for this podcast. I just think he’s a joy. He’s a real joy, and I think we always have something to learn from an absolute fucking legend. And he’s a legend to the bone, not just in what he does, but in who he is. So I feel quite different about the whole thing feeling different about him. Listen to it if you want. I don’t care. Please listen to this. Please enjoy it. Have a cup of tea. Relax. He’s such a great good egg. This is oh I can’t believe I’m saying it. This is Conan O’ fucking Brien. It’s my crush. It’s my hero. It’s Conan O’Brien. Hello. How are you? [00:03:44][224.8]

Conan: [00:03:45] That’s a lot. That’s a lot to put on me. [00:03:46][1.5]

Jameela: [00:03:47] I know. Sorry. You’re right. [00:03:48][1.3]

Conan: [00:03:48] Yeah, I think I’m going to be fine. Yes. I’m just imagining I’m David Bowie, and that’s where you’re directing it. [00:03:54][5.6]

Jameela: [00:03:54] Yes. [00:03:54][0.0]

Conan: [00:03:55] That’s the appropriate. That’s the appropriate place to send. [00:03:58][2.6]

Jameela: [00:03:58] I think of you as the David Bowie of late night, I think that’s fair. [00:04:01][2.6]

Conan: [00:04:02] I was the Bowie of Late Night, and we were lucky enough to have him on several times and he was lovely. He was. [00:04:10][7.8]

Jameela: [00:04:10] I didn’t know you interviewed him. [00:04:12][1.5]

Conan: [00:04:12] Oh yeah, he was terrific. Very funny. Played along with everything and very intelligent and one of my all time favorite people. So, his name just came up. I don’t know why, but there you go. Who’s better than David Bowie? I say nobody. [00:04:29][16.5]

Jameela: [00:04:30] Were you a big fan of his before you had to interview him? [00:04:33][3.0]

Conan: [00:04:34] Yes. Yes, I really was. And I just loved how he kept. I think my favorite quality in entertainers and artists is when they just keep changing. I love that. I always find that fascinating, and I’m amazed if you look at his arc just how many times he kept reinventing himself. So I admired that a lot about him. [00:04:56][22.7]

Jameela: [00:04:57] Yeah, except you and I had the same haircuts for 30 years. I mean, we admire it we talk the talk, but we do not walk the walk. [00:05:05][7.8]

Conan: [00:05:06] Well, we’ve changed in other ways. We went through change in other ways. [00:05:07][0.7]

Jameela: [00:05:07] You wore a denim jacket. for your final year. [00:05:09][2.3]

Conan: [00:05:12] That’s right. Yeah. So you know, that was my big change. Let’s see if the fans can handle denim. [00:05:18][6.3]

Jameela: [00:05:19] Do you feel like I wondered this about quite a lot of people, especially musicians, sometimes. But do you feel that as life becomes, as you become more successful, life becomes slicker, the show becomes slicker? Everything’s run kind of more smoothly, especially as we’ve gone into more of a digital age and things are more kind of controlled and therefore, I don’t know a little bit colder. Do you do you find that you miss the kind of scrappiness of before? [00:05:45][26.0]

Conan: [00:05:46] Yes, I know what you’re talking about when I started way back when we started a late night show. [00:05:52][6.7]

Jameela: [00:05:53] 28 years ago, [00:05:53][0.0]

Conan: [00:05:54] yeah, in 1993. And we didn’t really know what we were doing. And I’m trying to be really honest about it. NBC should not have given me a show. It was a mistake. I was way too green. And there was not enough supervision. And what we had was a lot of ideas of what the show should be, which I think later on were born out to be correct and worthy, and we had a lot of nerve. But we really didn’t know what we were doing. And I’m stunned that I found myself in that position and was able to push through it. And there was a lot that. There were shows that barely made it on the air. I mean, there were times when we delivered the show minutes before it needed to be put into a machine and a button pressed and then, you know, [00:06:52][58.4]

Jameela: [00:06:54] a pigeon would carry it. [00:06:55][0.9]

Conan: [00:06:56] Yeah exactly a pigeon in a pneumatic tube. [00:06:57][0.6]

Jameela: [00:06:58] Right? [00:06:58][0.0]

Conan: [00:06:59] But yeah, so I was had just turned thirty. I was twenty nine when I auditioned, I had just turned 30 and I look at. Someone, the other day, one of my friends found online a promo that I made before the show went on the air, and I look about sixteen years old and and I positively sound prepubescent and I just can’t believe that that guy got such a high profile show. And we didn’t know what we were doing, so I missed that part. I missed the scrappiness of it. I miss the ragged edges sometimes, but I could never live that again. Because I think it would kill me. It was too scary. It was really scary. [00:07:47][47.8]

Jameela: [00:07:47] Yeah, especially if you have anxiety, which I really want to talk to you about. I mean, this is predominantly a mental health podcast and and I feel as though you’ve been so honest and open, always in a very like fun and funny and relatable way. But about the fact that you have. Can I say, struggled with your mental health? Would you call it a struggle or you’ve just sort of. [00:08:05][18.0]

Conan: [00:08:07] Yeah I think everybody I mean, I think a lot of people have I wouldn’t say everybody has because I can’t speak for everybody, but [00:08:10][3.4]

Jameela: [00:08:13] I’m perfect. [00:08:13][0.5]

Conan: [00:08:14] We know that, [00:08:15][0.9]

Jameela: [00:08:15] Yeah, this is a charity podcast for people like you. [00:08:17][2.4]

Conan: [00:08:18] I I just did a Google search on perfect mental health and your your picture came up. Beautiful shot of you. [00:08:24][6.1]

Jameela: [00:08:24] Thank you very much. [00:08:25][0.4]

Conan: [00:08:26] Yeah, I would say that to be fair. And again, I can I can say that it’s in my family line anxiety specifically. I think we’re anxious people and I can see it in my immediate family. I can see it in the family tree. [00:08:47][20.2]

Jameela: [00:08:49] And it’s what’s that from like, what’s the? Is there a thing that happens throughout your lineage? I know that you are 100 percent Irish. [00:08:57][8.0]

Conan: [00:08:57] Yes, I’m 100 percent Irish. [00:08:58][1.1]

Jameela: [00:08:59] I’m not saying anything here about Irish and being anxious, just to be clear, but, that’s all I really know about your lineage is that you you feel very fondly about your family and you are 100 percent Irish. [00:09:09][10.3]

Conan: [00:09:11] I’m 100 percent Irish. I had a genetic test about three years ago and I ended up talking about it on stage a lot in a tour, which is I got the news that I was 100 percent Irish and the genetic doctor who told me that said, this is very rare for anyone. And he said there aren’t there aren’t people that live in Ireland that are 100 percent Irish. They’ve got a little mix of. [00:09:37][26.2]

Jameela: [00:09:37] Congratulations. [00:09:37][0.0]

Conan: [00:09:37] Yeah, they’ve got like a little mix of some Spanish in there. They’ve got a little Dutch, they’ve got a little this, they got a little of that. [00:09:43][6.0]

Jameela: [00:09:44] So nobody wanted to shag your ancestors then. That’s great. [00:09:48][3.1]

Conan: [00:09:48] Well, no. But what it turns out is our ancestors just wanted to shag each other. I figured out very quickly it means I’m inbred. Really inbred. Hundreds of years, hundreds and hundreds of years of a brother looking at a sister and saying, You know, it’s raining out again. No, I I think there’s something. I mean, famously, the Irish and this. I think this is a safe generalization. But we were known to self-medicate using what’s available, usually Guinness or something. But there is, you know, there’s I think there’s a strong correlation and I can’t say, look, I think there’s many different people around the world that have problems with anxiety. But I know that for me personally growing up, I remember thinking around the time that I was in the fourth, fifth, sixth is really started in fourth grade and fifth grade and sixth grade. I’m just anxious all the time. I’m just anxious and I remember [00:10:55][66.7]

Jameela: [00:10:55] What were you anxious about like what kind of things does someone in fourth grade worry about? [00:10:59][4.0]

Conan: [00:11:00] Uh, I think I moved to a much bigger school. I come from a really big family. My mom went back to work, so both my parents were working. She wasn’t around a lot. And I think I felt completely lost in the shuffle. And I think I also, you know, my knobs are probably turned up a little high on, you know, how I perceive what’s going on. And this is a strange environment, do people like me. Do they not like me? Dealing with a lot of insecurity. I was not a good athlete. I did not think of myself as a smart person. And it’s so funny because later on, people started to say, Well, you know, you’re really smart. And I would think I had no idea. And I don’t think of myself that way. And when I was a kid, I really didn’t think that I was intelligent and I didn’t think I had much to offer. So you add all those things together, and I remember just, you know, I hated going to school, hated the ride to school. It was a carpool. And every second that we were riding there, I kept thinking, Well, we’re not there yet. We didn’t cross the trolley tracks yet. So we’re not there yet. Just kind of that sick to your stomach queasiness. [00:12:21][80.9]

Jameela: [00:12:23] Do you know where that came from? [00:12:24][1.2]

Conan: [00:12:25] I don’t, you know, it’s funny because I’ve had my share of therapy and everything, but I [00:12:31][5.7]

Jameela: [00:12:31] it feels like you were waiting almost for the rug to be pulled from under you. [00:12:34][2.7]

Conan: [00:12:34] Yeah, and I think there’s still, you know, I still have that at times you just think there is. You know, and duh, this is probably where some of it comes from. My father is an, I think is an anxious person, and he used to say to me anxiety he thought was a good thing because it spurred you to work harder. It made you more cautious. If you’re anxious and you’re worried, you’re probably looking around the you’re looking ahead. He used to say to me, accidents are usually a failure of imagination, so he’s kind of a [00:13:17][42.8]

Jameela: [00:13:19] That’s amazing. He’s a philosopher. [00:13:19][0.0]

Conan: [00:13:20] Yeah, he kind of was a my dad was and I love my dad and he’s a great guy, a brilliant guy and very [00:13:30][9.0]

Jameela: [00:13:30] Bit of a downer sometimes? No I’m kidding. [00:13:31][0.6]

Conan: [00:13:35] Yeah no. But you know, to be fair to him, I think he just thought that if you’re careful enough in life, you can avoid problems. And I remember thinking, I think I swallowed my dad’s philosophy like, Oh yeah, OK. [00:13:52][17.0]

Jameela: [00:13:53] Like a survival mechanism. [00:13:55][2.4]

Conan: [00:13:56] Yeah, like a survival mechanism. But of course. When I look at my career now. Some of the best things that happened to me were me taking crazy chances. I mean, graduating from, you know, this really good elite college and decided to go out to L.A. and try my hand at being a comedy writer felt like it in retrospect feels kind of risky. [00:14:21][25.2]

Jameela: [00:14:22] Yeah no one goes from Harvard to working on like The Simpsons. I think it’s amazing that you did. I’m like, obviously like Mike Schur now and all these [00:14:32][9.9]

Conan: [00:14:35] You know it’s funny it became it became this like more acceptable thing to do. And now it’s the equivalent of being like a stockbroker in the 1950s. [00:14:41][5.4]

Jameela: [00:14:41] So this is the eighteen hundreds, you know, this is a different time. [00:14:44][2.6]

Conan: [00:14:46] I should point out I was born, to be fair, in the late 1800s. I was born in 1898. But no, but it’s funny that it was. I just look at some of the things that I’ve done in my life, and I thought that was a crazy chance to take. And then I took a bunch of chances here and there. And yeah, I am very I realized in a weird way, I’m very comfortable with that chaos. I’m really comfortable taking a chance and one of my, you know, if I’m on stage and things start to go off the rails, it’s the opposite of scary. It’s actually kind of thrilling and fun. And and some of my favorite moments have been accidents. So it’s very strange to grow up being afraid of a surprise or being afraid of something not going well and then actually find yourself in a profession where. I mean, getting up in front of people to try and make them laugh, I don’t care who you are. It doesn’t work all the time. It just doesn’t. And when it goes badly, it’s awful. It feels just as badly. [00:16:03][77.3]

Jameela: [00:16:05] I’ve always wondered this what goes through one’s head when they’re bombing on stage. Because I’ve always been like too. I’ve done standup one time ever. I did it at Largo and it was the most exciting and exhilarating thing I’ve ever done. And it went well and I was like, Right, that’ll never happen again. And I don’t have the. I don’t have the gumption to ever try this ever again. And I’ve always wondered because I’m so afraid of that feeling of dying on my absolute ass. What does that feel like? [00:16:35][30.1]

Conan: [00:16:36] Well, not that I would ever know. [00:16:38][1.8]

Jameela: [00:16:39] Yeah, of course. [00:16:39][0.3]

Conan: [00:16:40] I mean, I’ve read books about it, and it counts. [00:16:42][2.0]

Jameela: [00:16:43] Sad sad for them. [00:16:43][0.0]

Conan: [00:16:46] No I will tell you that it. I’ll tell you exactly what it feels like at first. It’s terrible, absolutely terrible to be trying to get people to laugh, and it’s not working. And what happens as as you go on in life is it starts to be terrible. And then the worse it gets, suddenly something happens where it’s kind of funny. You just think I’m getting nothing and this has happened. I’m going to say mostly when it has happened it’s been a charity event where they they book you and they say, We’ve got Conan O’Brien. It’s going to be great. And it’s a really big room that’s not built for comedy giant massive and deep. And they serve dinner and people are getting their food. Literally, waiters are handing them their food and they’re eating and you hear silverware, and then there’s no proper warm up or introduction. A voice just says, OK, everybody, Conan O’Brien. And then suddenly you start walking up the dais and you realize I can hear my feet. I can hear my leather of my shoes squeaking, and I hear a lot of eating and there’s no sense of occasion and there’s no focus and you get up there and you’re like, OK, everybody welcome. You know, we’re going to try and erase glaucoma today. Speaking of erasing glaucoma and people are looking down at their food and occasionally they’re looking up. And what’s interesting is that no one. In your mind, you’re thinking, Oh my God, I’m bombing. They’re not even thinking about you that way, they’re just, Oh, this veal is better than I thought it was. I wish it had a sauce. It doesn’t have a sauce and wonder if I can get the waiter’s attention. [00:18:38][112.6]

Jameela: [00:18:39] I imagine them thinking of you as a veal. [00:18:40][1.1]

Conan: [00:18:40] Yeah, maybe. Well, I’m pale. [00:18:44][4.0]

Jameela: [00:18:45] A talented veal. [00:18:47][1.7]

Conan: [00:18:48] Yeah. But it is funny that you get to a point if you, I think with experience comes. OK, I’ve know what it’s like to do well in front of a crowd, and I’ve done that enough to know that this is not a referendum on my character. This is just one of those nights. And [00:19:05][16.8]

Jameela: [00:19:05] It’s also sorry. It’s also that reminds me quite a lot of social anxiety. I was telling my I was telling my boyfriend about this that, you know, when he used to worry about what people would think about him when you know, we would go to a party cos he has terrible social anxiety, or he did anyway. I just feel like no one is thinking about you being shit. Everyone is having the same worry about whether they are being shit. And so while you’re scrambling to find the end of your story or in your head, you’re scrambling. They’re all just panicking about what their story is going to be, what they’re going to contribute to the story. Everyone is so kind of navel gazing and terrified that we presume everyone is focusing on us much more than they are. Obviously, that’s different and very heightened if you’re literally on stage and everyone is supposed to listen to you and they aren’t. But, but it is kind of the same thing. [00:19:53][47.4]

Conan: [00:19:53] They will quickly move on with their lives. They will very quickly forget that I was even at the benefit. And I think that’s the other thing too, is it is very calming to realize that this planet is filled with billions and billions of people, and most of us are very self-involved. So that does take away some of you know, I don’t know if you’ve done cognitive therapy, but I’m a big. [00:20:23][29.9]

Jameela: [00:20:24] I have. [00:20:24][0.1]

Conan: [00:20:24] I’m a big believer in cognitive therapy. I’ve tried lots of different things, but one of the things that I loved about cognitive therapy is that we are machines, we are, you know, we’re biological machines, and we our brains work a certain way and we’re flawed. We if and if you start with the premise that we’re flawed and that evolution still needs to probably work on us for a couple hundred thousand more years for us to improve if we even get that shot. If you take that premise that we’re flawed, you start to realize, Oh, I can detach myself a little from my brain and I can sort of start to map out how it works. And so I can see, Oh, I’m doing that thing again. I’m doing that thing where I, you know, Jameela says, something that makes me that triggers me, that everyone thinks I look like a veal. Then I go. [00:21:28][63.2]

Jameela: [00:21:29] I was not saying I think you look like a veal! [00:21:34][4.2]

Conan: [00:21:34] Well you’re the third person today, anyway. But then I start to go into a spiral. And you know what the first thing I did when I went to cognitive therapy is the therapist who was very good said, When you’re having this, you know, I’m no good. My career is over. I’m it’s all collapsing. No one ever really liked me. I’m a failure. All the things that people can think about themselves, regardless of what you do. If you write it all down on a sheet of paper as you’re thinking it and then walk away from it for ten minutes and then go back and look at it and read it, it looks ridiculous. Do you know what I mean? [00:22:18][44.2]

Jameela: [00:22:19] Yes I believe in writing everything down. [00:22:20][1.1]

Conan: [00:22:21] And and so there might be a moment where you would think I’m unattractive. I’m this. I’m that I’ve gotten nowhere. People hate me and you would write that all out. And then you, Jameela, would go back and look at it ten minutes later and say, This is all shit. What are you talking about? This isn’t true. None of this rings true. This is neuroses when you get ten minutes away from it and it’s on a piece of paper and you’re able to revisit it just looks false. It just does. You know, and you’re able to get a little distance on it in the moment that it’s happening and you’re having your anxiety attack. It’s all encompassing and it all feels true. So that’s one of the things I like. And when I talk to my kids, I have a seventeen year old daughter and I have a 15 year old son. And if they’re having anxiety, I do talk to them about. You know, [00:23:20][58.8]

Jameela: [00:23:21] perspective, [00:23:21][0.0]

Conan: [00:23:22] perspective and saying, OK, what is it you’re worried about, get them to say it out loud and then say, really? So let me get this straight. No one likes you or you’re you’re you’re not good at math. Well, actually, no, I’m I am good at math. Oh, but you just told me five minutes ago, I’m no good at math. Well, actually, I I didn’t mean it that way. Well, that’s exactly what you said. So you just start to divorce the these panicked thoughts. [00:23:52][29.6]

Jameela: [00:23:53] Panic lies. [00:23:53][0.3]

Conan: [00:23:55] Yeah, they’re lies. [00:23:55][0.4]

Jameela: [00:23:56] We had a guest on here say that depression gave him fake news. I feel like that was one of my favorite expressions around that. I’m sorry, I was just taking what you said and then to sort of make my finding a more beautiful and condensed. [00:24:10][13.5]

Conan: [00:24:10] Sure. With a clearly better [00:24:11][0.5]

Jameela: [00:24:11] with a better guest, [00:24:12][0.5]

Conan: [00:24:13] Clearly better guest. [00:24:13][-0.2]

Jameela: [00:24:14] He’s my favorite. He’s so great, by the way. [00:24:16][1.7]

Conan: [00:24:16] Oh, I love that guy. I love that guy. When I first started to get some help. Uh, years ago, I was convinced I said I am not depressed and I had a real chip on my shoulder about I am not depressed and I do want to be fair that I I’ve read accounts of people that have gone through just intense depression where they can’t get out of bed. And I mean, they need incredible intervention and it’s life threatening. And I’ve never had that ever ever for a second ever had that. [00:24:56][40.2]

Jameela: [00:24:57] What was yours? How did yours manifest then? Because mine was the same. I was high functioning, so I didn’t know I had depression. I thought that you had to cry all the time. [00:25:04][6.9]

Conan: [00:25:04] Exactly. That’s what I thought. And so when someone was saying what I think you might be depressed, I was very argumentative and I was like, No, that’s not me. I’m anxious. I’m anxious. That’s not the same. And then I started to learn that anxiety is a perpetual anxiety is a type of depression or a subset of it, and that it can all fall under the same. It’s not an either or. And the other thing that I heard was this great definition of depression. Someone said to me, which is it’s anger turned inward. And I thought, That’s fantastic. You know, it is. I never thought of it that way. But it is. It really is anger at yourself. And you know, when it it’s when it’s at its worst, it’s rage directed at yourself. And so that’s what I tried to attack is, Hey, what did I do that was so bad? Why am I, you know why? Why am I picking on myself so much? Why am I putting myself through this? Because that’s what we are doing a lot of times in some way. [00:26:16][72.1]

Jameela: [00:26:17] Mine is a different kind of repressed rage where I’m not mad at myself. I’m actually mad to other people and I’m not being brave enough to say something and stand up for myself. And that frustrates me with me. But generally, I am one of my ways out of depression was deciding to be the smaller man instead of the bigger man and actually get pettier and never rise above. When they go low, we go lower. [00:26:44][26.9]

Jameela: [00:26:44] You know, I love that I want that. [00:26:45][1.1]

Jameela: [00:26:46] That’s my presidential slogan. [00:26:48][1.8]

Conan: [00:26:50] I want that. Let’s uh the Obamas have the other slogan, so let’s trademark that one [00:26:53][2.9]

Jameela: [00:26:54] 2024 you and me. [00:26:55][1.1]

Conan: [00:26:56] I love when they go low, we go lower. I would I would wear that shirt. [00:27:00][4.2]

Jameela: [00:27:00] It really helped. It really cured my it really, I wouldn’t say the word cured, but it massively alleviated. [00:27:05][4.5]

Conan: [00:27:06] Oh no, God, no, no, you’re not cured. [00:27:07][1.8]

Jameela: [00:27:10] I’m not cured. [00:27:10][0.3]

Conan: [00:27:11] Jesus, Jesus Christ, you’re the worst. I mean, you just get worse and worse every time I everytime I talk to you. [00:27:13][1.9]

Jameela: [00:27:13] I’m falling apart. [00:27:17][4.3]

Conan: [00:27:18] You’re completely falling apart. It’s fascinating that you say that because there’s this. I was raised very Catholic and my mother as we were growing up. There is this Catholic idea, Christian idea, but the Catholics have really taken it and it was offer it up, offer it up. So my mother would always say, if something’s bothering you or if someone’s irritated you or someone’s done something she would say, offer it up to the suffering souls in purgatory meaning. Just and and I remember at the time thinking [00:27:54][36.6]

Jameela: [00:27:54] I don’t know what that means, offer it up, like [00:27:56][2.0]

Conan: [00:27:57] offer it up almost like a prayer, like, oh, that person just cut me off in traffic and took off my front bumper and then tore off into the night. So I’m going to take all that anger and rage towards them and just offer it up. And like as an offering, I’m going to give it up to the universe and it will just magically disappear. And and I was like, even as a kid, I thought, Huh, OK, well, my mom’s telling me, this must be good and it doesn’t work. That doesn’t work. You need to accelerate, then force that person over to the side of the road and then take the bumper off the front of your car that’s hanging there by one bolt and beat them with it. [00:28:46][49.1]

Jameela: [00:28:46] And will you take a shit on the the driving seat as well? [00:28:49][2.7]

Conan: [00:28:50] That’s a lot of pressure to take a shit on cue like that. [00:28:51][1.6]

Jameela: [00:28:52] Oh I’m sorry have I gone too far? I’m so sorry that I lost control in this scenario. [00:28:59][7.3]

Conan: [00:29:00] I’m sorry, but you now are invoking think about the anxiety involved you defecating on cue on cue. [00:29:08][7.9]

Jameela: [00:29:09] You’re being horribly violent but I’ve gone too far. [00:29:10][1.1]

Conan: [00:29:10] Yes, you have. You have, because that’s unsanitary. I was just going to clump him once on the side of the shoulder. [00:29:17][6.6]

Jameela: [00:29:17] I’m sorry, I didn’t realize that this is a civilized conversation. [00:29:20][2.5]

Conan: [00:29:22] This was a civilized attack. This was just me enforcing certain societal rules. And now you brought in defecation. And so you have a lot of work to do, and I’m double down on this idea that you’re getting worse and worse. [00:29:34][11.7]

Jameela: [00:29:35] Ah, but I do. I really do. I really, you know, I’ve spent kind of the last nine years now since I made that decision. Maybe 8 years. It just in the gutter like I jumped down and I’ve I’ll fight, I’ll fight you like that. I’m just like, I’m all about that. And while I think that it’s important to make sure that you never become the aggressor, it’s all like it has helped me personally to and people say, you know, don’t use your energy for that. But if I don’t use my energy for that, I end up using my energy kind of consoling myself from all the shit that I’ve had to swallow, like having to digest all of someone else’s bullshit that I have just swallowed against my integral will. [00:30:15][39.3]

Conan: [00:30:16] It does not work. Very simply, it doesn’t work. Now, that doesn’t mean, as I, you know, it doesn’t mean you have to beat them with a bumper or defecate on their front seat. You don’t have to do those things, but standing up for yourself is a very healthy thing to do. And swallowing anger. It just has to go somewhere. So when you internalize that stuff, disappointment, anger and I was so uncomfortable being, you know, feeling like I had to confront people about things. It was problematic and I would just internalize it. So so I [00:31:03][46.8]

Jameela: [00:31:03] You would try and offer it up, and it would just sort of piss back down over you. [00:31:05][2.4]

Conan: [00:31:06] It would piss back down on me and I [00:31:07][0.4]

Jameela: [00:31:07] When did you stop doing that? Was there like a moment where you were like, Fuck this, I actually can’t do this anymore? [00:31:12][5.1]

Conan: [00:31:13] I want to say once I started doing The Late Night Show and I was under so much pressure, there was just no way to do that anymore. And I remembered when I when I came to New York to do The Late Night Show and I was 30. I remember going to a restaurant with with someone and the waitress said, Oh, we have this lovely salad, and she listed nine ingredients and I remembered I loved eight of them. But the ninth ingredient was something I really didn’t like, which is olives. I don’t like olives. And so I remember thinking, Well, I can’t get that. And my friend said. Why don’t you ask them, can you get me that dish but just leave off the olives? And I said, and I’m a 30 year old man at the time and I said, Oh, she’s going to think I’m like a dick. If I ask her to leave off and I’m one of those fussy customers and I don’t want her to be mad at me, and they’re like, What are you talking about? That’s called ordering in a restaurant? I’ll have this. But could you leave off that and that and then put this on the side? That’s the state of development I was in at the age of 30 as I thought, I’m going to get in trouble if I ask her to leave off the olives. [00:32:30][77.1]

Jameela: [00:32:31] It’s so funny you say that this again, is part of my philosophy. As I started with changing my orders, that was my micro. No. Yeah, it was how I began. That was my kind of that was the a gateway drug to stand up for myself was just starting to advocate for myself in really tiny ways. [00:32:46][15.1]

Conan: [00:32:46] But that’s one of the things that they in cognitive therapy they encourage you to do is you’ve got to start small, but you’ve got to do it. It’s like anything else. It’s like doing sit ups or push ups. You’ve got to just start and then you. It has to be consistency. So every day. And for me, mine was if I knew the right way to go and I got into a cab and the cab driver was taking me the wrong way. It’s OK to suggest a better way. You’re not an asshole if you suggest a better way. And you do it nicely. Do you know what I mean? And I had trouble doing that. So it took me a while. I had this little micro assignments like, could you please leave off the olives and could you please, you know, maybe take the West Side Highway. I think that’s going to go a little better at this time of day in my experience. [00:33:43][56.6]

Jameela: [00:33:43] What about the shagging? With shagging were you ever good at being like I don’t love that, I don’t love that. Could we do this differently? [00:33:50][6.8]

Conan: [00:33:51] I was just happy that it was happening. Let’s just say beggars can’t be choosers. I was just so happy. [00:33:58][7.0]

Jameela: [00:33:58] I’ll eat the olives. [00:33:58][0.0]

Conan: [00:34:02] I’m here. I’m naked. This is actually happening. I’m not watching Cinemax. This is incredible. [00:34:10][7.6]

Jameela: [00:34:11] Just shut up before it goes away. You’ve gone a bit red, sorry have I embarrassed you? [00:34:20][9.5]

Conan: [00:34:22] It’s ok. That’s also probably, probably high cholesterol, too. It’s a mixture of blood pressure and embarrassment. [00:34:28][6.0]

Jameela: [00:34:29] And being 100 percent Irish. [00:34:29][0.2]

Conan: [00:34:31] I am not. No, I am not. I am not some terrorist with a list of demands in the bedroom. [00:34:36][5.5]

Jameela: [00:34:39] No, I don’t mean that. [00:34:40][1.1]

Conan: [00:34:41] I can’t stop. [00:34:42][1.3]

Jameela: [00:34:43] I’m not saying, do you have like a Chilcot inquiry level. Just sort of like, you know,. [00:34:47][3.7]

Conan: [00:34:47] Here’s what’s going to happen see. [00:34:48][0.9]

Jameela: [00:34:51] No but if like you know like some people can use too much tongue. You know what I mean in the in the mouth. And and so have you been in that situation where you’ve ever been like, because that was a big that was a big one for me where I was like, Oh, wow. Advocate for myself. Or I was just like, Hey, I would prefer it. If we actually kiss a bit more like this, this would work for me. Could we try it? And then he ended up finding that fine, and then this was like when I was like, 25 years old. And then we ended up having really nice kisses after that, and I was like, Oh my God, the amount of bad kisses I’ve had and bad shags I’ve had because I never just said, Oh, can we just. that was my version of leaving off the olives like leave out all of the tongue, you know? [00:35:30][38.3]

Conan: [00:35:30] Right, right, right. Could you wear this presidential mask? [00:35:33][2.6]

Jameela: [00:35:34] Yeah. [00:35:34][0.0]

Conan: [00:35:38] I have a great collection of 19th century presidential masks. [00:35:41][2.7]

Jameela: [00:35:42] Your lucky wife. Which one of you wears them? [00:35:42][0.0]

Conan: [00:35:47] Yeah no. She drew the line. This is before my wife. You know, it was always getting getting the woman to wear the Martin Van Buren mask was always the trickiest one. They just I don’t know why they always drew the line at Van Buren. But no, but I it’s so funny you say that because so it sounds to me like this person who was using too much tongue. They they probably thought they were overthinking it. They probably thought, Oh, the ladies love this and basically what he is, he sort of Roto-Rooter. He’s just like, he’s like a blender. Yeah, you know, and it’s that’s he’s not just in the moment. He’s thinking time for the old tongue action that always gets ’em. [00:36:30][43.7]

Jameela: [00:36:31] Yeah. Well, that’s also because no one’s ever said, Hey, this is like an attack inside the mouth, you know? [00:36:39][7.2]

Conan: [00:36:41] He was giving you a cleaning, you know, did you ever notice that [00:36:43][1.9]

Jameela: [00:36:44] That was it. Yeah, you know, like my hygienist didn’t have to, I fired my hygienist. [00:36:48][4.4]

Conan: [00:36:49] My hygienist was just like, You have no plaque. This is incredible. You haven’t had a cleaning in six years and you have nothing in here. [00:36:55][6.2]

Jameela: [00:36:56] I strongly, I strongly I strongly suggest anyone listening to this, like, I think that’s a really also important way is in the bedroom. I feel like that’s such a fundamental way to be able to advocate for yourself. You don’t have to give anyone like, you know, an itinerary, but a little like, Hey, you know, we had Shadeen Francis on this shows a sex therapist who talked about. We’re not going to talk about sex the whole time, even though I know that you love that it doesn’t make you feel at all uncomfortable, but. [00:37:20][24.8]

Conan: [00:37:21] Not at all. [00:37:21][0.4]

Jameela: [00:37:21] She talks about the fact that when you’re cooking for someone, right, it’s it’s very normal to be like, Hey, is there anything you don’t eat? And so, you know, it’s so funny that with when it comes to sex, it’s like, you shall eat what you are given. [00:37:32][10.5]

Conan: [00:37:41] Brussel sprouts for everyone. It’s so funny because we had I’m blanking on her name now, but we had a sex therapist on the late night show in the 90s, and she was just so straightforward and just saying, OK, this is what women like. This is what they don’t like. And I remember thinking, Where were you twenty years ago. Do you know what I mean? [00:38:00][18.8]

Jameela: [00:38:00] 100 percent. [00:38:01][0.4]

Conan: [00:38:04] Because I was so I was getting the news late, relatively late. [00:38:07][2.6]

Jameela: [00:38:11] Is that via no news at all? [00:38:12][0.8]

Conan: [00:38:13] Yes exactly. There was a news blackout and I am someone who didn’t know anything. And so just, you know, and then of course, the this was all pre-internet where I mean, just it’s knowledge and and there’s way too much information about sex everywhere constantly. And it’s popping up on my watch and it’s it’s all the time. [00:38:42][28.9]

Jameela: [00:38:42] It’s not a normal part of the watch. Just so you know, yes, you have to download that, especially on the Apple watch. [00:38:48][5.6]

Conan: [00:38:49] I got a special Apple watch. Yeah, it’s got a massive screen. And but I grew up in that era where like, you’re hearing things from friends. Who are saying things like, well, basically how it works is you. This is a friend actually told me this. I think I was in like the fifth, fourth or fifth grade. I was like, he parks his car in her garage and I was like, got it. [00:39:15][26.7]

Jameela: [00:39:17] I’m ready. [00:39:18][0.5]

Conan: [00:39:19] I’m all set to go. That’s I mean, what is that? And then to actually start interviewing sex therapists through my job on television and having them say, OK, you want to do this, you don’t want to do that. This is good. This is you could try this. You could try that. This is a good spot. And then you might want to do this and you’re like, Jesus, I love invoking Jesus when having these conversations. Jesus, Mary and Joseph. Where was all this? I was operating on so little knowledge. Literally, someone had told me, You’re going to land this airplane. And all they said was, stick, go down plane, go down. And no one told me about the no one told me about the altimeter. No one told me about the ailerons. No one told me, you know, this was nice to get some information, so I don’t know. But now, of course, kids are getting crazy amounts of information at a at a very early age, and I don’t know what that does to them so who knows. [00:40:23][64.2]

Jameela: [00:40:23] Yeah, I don’t yeah, I don’t know how I feel about the first time you learn about sex being almost entirely from the internet. I do think some of it is should be practical. [00:40:34][11.4]

Conan: [00:40:36] Yes. [00:40:36][0.0]

Jameela: [00:40:37] You know what I mean? I feel like there’s there’s more intuition as to what you as individuals like. We’re not a monolith. We are all like the same things. We’re not. People don’t respond in all the same ways. I feel as though it’s it’s definitely a shame that so many people are having so many of their first kind of sexual interactions online because you can’t really instinctively feel. And I’m not anti or, you know, pornography or sex talk or anything like that. I think that’s great. I think, you know, creates access for those who don’t have it, but I definitely feel like I know some of this should be learned with your hands. You know, like I said, like how what you like, what they like? Otherwise it’s too intellectualized. [00:41:13][36.9]

Conan: [00:41:17] Yes yes well as the sex robots get better which they will, you know, they’re going to, [00:41:21][4.2]

Jameela: [00:41:22] you’ve noticed they’re getting better. [00:41:23][1.0]

Conan: [00:41:23] I keep going by the store and I haven’t been out for a while they just look like for awhile they were just washing machines with mannequin arms. And I was very unhappy and I would look, you know, I’d go through the store, but they’re just going to get better and better and better. And and then there’s going to be people. You’ll be at a party having a full on amazing conversation and you realize this is a sex robot. This is a [00:41:45][21.2]

Jameela: [00:41:47] I don’t know. I’ve been in L.A. for about eight years now, and I already have that thought when I’m talking to some people. [00:41:54][6.6]

Conan: [00:41:54] You think this is a sex robot. [00:41:56][1.5]

Jameela: [00:41:56] I think this is a sex robot. [00:41:57][1.0]

Conan: [00:41:58] Yeah. [00:41:58][0.0]

Jameela: [00:42:02] In this episode, I quote previous guest Matt Haig’s line Depression gave me fake news, and if you like this episode, then I think you would really like my conversation with Matt Haig. We talk about his experience with depression and how social media impacts mental health, why he’s so grateful that he pushed through his mental health struggles and his incredible, groundbreaking book Reasons to Stay Alive. Go give it a listen. But enough about shagging, Conan, if you don’t mind. [00:42:28][26.5]

Jameela: [00:42:29] All right. I mean. I just think there’s a lot more to talk about here. I’ve got some drawings and etchings I’d like to show you. [00:42:37][7.9]

Jameela: [00:42:38] That would be great. We could maybe present them at the end of the show. I do want to talk. I want to talk a little bit more about the depression. So with. So when it comes to like advocating for yourself, it’s like a big part of kind of changing. And how did that start to make you feel just more in tune with yourself more integral more in control? [00:42:56][17.9]

Conan: [00:42:57] I think I’m a big believer in talking to somebody and there’s when I do my podcast, [00:43:06][8.9]

Jameela: [00:43:06] what do you mean? Like confrontational? You mean therapy? [00:43:08][1.5]

Conan: [00:43:09] I mean in therapy. And I think that I probably still have a ways to go with confrontation. But. But I think that talking anything that when you’re just trapped inside your head, it’s easy to start drawing all the wrong conclusions, and I think that’s where anxiety, that’s where depression can build. I think the more that you can speak and get these ideas out of your head and then realize, Oh, wait a minute. Lots of people feel this way. Lots of people have these thoughts. I’m not special. I’m not this once in a millennia genius that just happens to have this very unusual way of thinking. [00:43:58][49.0]

Jameela: [00:43:58] Speak for yourself. But yeah, okay. [00:43:59][1.2]

Conan: [00:44:00] No, no, no. You are. Yes. I wouldn’t say millennial. You know you’re 600 years. You’re a once in a 600 year genius. [00:44:05][5.4]

Jameela: [00:44:05] Thank you. Thank you. I feel very seen. [00:44:06][1.0]

Conan: [00:44:09] My my, my type of genius crops up roughly every four months. And in many different places in the world simultaneously. So I can’t feel too special about it, but talk about it and get it outside of your head. Get it out of you. And then you will start to realize, I think that, oh, this is a pattern. This is a way a lot of people feel. And that in itself, I think, is very healing. I’m not so special. Like, I think you talk about that. You know, you talk about celebrity or performers and they what’s really at the crux of all that is I want everyone to see how special I am on some level, but it’s also really healthy to realize you’re not that special. You know that we you know, when I was growing up, obviously an old man, but in the 70s, there was this big movement like everybody’s so special and you’re so special. And everyone’s and I I sometimes used to think as I got older, it’s kind of healthy to realize that I’m not that special, that plenty of people feel the way I do. And you don’t feel so alone. Do you know what I mean? [00:45:33][84.2]

Jameela: [00:45:34] Yeah I do except then you know, we end up in this fucked up industry where everyone is hyperbole using just how special we are almost in a way to kind of control us, you know, like to kind of pander to our egos, tell us we’re special we’re special, we’re special. And so it’s an extra kind of and it’s a really vital effort to make sure that you remember that, that that that is not really true. [00:45:55][20.5]

Conan: [00:45:56] Right. And you and I have both met countless people who will go unnamed, who buy into it. They buy into it, and it makes them more and more unhappy [00:46:06][10.1]

Jameela: [00:46:07] What about Russell Crowe. Like, just like, popped into your head no I’m joking, [00:46:10][2.0]

Conan: [00:46:13] I think the time he punched me out maybe. No it’s just so this is what fascinates me. You and I both get to work in this business where that people kind of idolize people, love they think, show business and getting to walk on a red carpet and be known and occasionally get some free stuff is absolutely amazing. And it’s a very American dream. And people obsess about celebrity. And my question is, why are so many of them so fucking unhappy? There’s a lot of people that are just really miserable. [00:46:53][39.8]

Jameela: [00:46:54] I don’t know anyone happy. [00:46:55][0.7]

Conan: [00:46:57] You don’t. You don’t know anyone who’s [00:46:59][1.4]

Jameela: [00:46:59] No, but I’m serious. Like, I really don’t know anyone who’s like, really happy and well or has been throughout the entire experience. I think all the people I know who were starting to come to peace are all kind of like in their 50s and 60s. I don’t know anyone who’s young who’s really happy. They smile on the red carpet, but they’re all there. I mean, they’re fucked. [00:47:20][21.8]

Conan: [00:47:22] Well, they’re terrified. And you know, I know that you. I, you know, I know that you worked with in The Good Place, you worked with Ted Danson, and he’s an example to me of someone who was very famous, very young and has had this just incredible success, you know, in film and television, and it’s just this unrelenting success. But whenever I’m around him in the times, I talk to him. He’s such a lovely guy and he’s there’s this zen calm that comes out of him. And I think that if I could get in a time machine and talk to him at 25, I probably wouldn’t get that. [00:48:03][41.1]

Jameela: [00:48:03] No. Even at 40, you wouldn’t have gotten that. He’s so open about it. It’s one of his favorite things about Ted. [00:48:07][3.7]

Conan: [00:48:08] Yes, he is. He has been. He has been through the mill and he now. It’s such a cliche to say someone gets it. He just gets it. He understands he has this deep understanding of, you know, probably what it’s what it’s. He’s been through so much and he has this understanding of just how to be. And he’s whenever I encounter him. I think if there’s any like disease in my body, it will go away because I’m talking to Ted Danson. He’s just such a lovely man. And I believe that that comes with age and [00:48:48][40.5]

Jameela: [00:48:49] Yeah he chases simplicity. He chases gratitude like he would skip physically, skip around the set and be like, aren’t we’re so lucky to be able to do this. Aren’t we such a great group? Aren’t we so lucky that we have all this chemistry and all this fun together, and we’d be shooting until one o’clock in the morning and he would be exhausted. We were all exhausted, but he’s also in his seventies and it’s 119 degrees outside, and he’s just still unrelenting in his enthusiasm. No, not a complaint. And this is a man who this could not be less new to, but he treats as if his new he’s like he is so determined to not to not take anything for granted again, because I think once he used to and he was fucking miserable. And so he hangs onto that. But also, he’s fucking he’s obsessed with Mary. He’s obsessed with her. Like she would be driving in the little golf cart. That’s his wife, Mary. Who they met at 50, which is also just amazing and so beautiful, but he was whenever she would come to set, she’d be driving down the little golf buggy and he’d be watching her and he, literally, like a baby, would almost beyond his own control to start doing a little clap to himself and giggle because he was so excited to see her. So he’s really, like, refined his life to be very much about only doing work that you love, making sure that you are grateful all the time and then really just surrounding yourself with the most wholesome and kind and simple and funny people. He’s absolutely nailing it. [00:50:16][87.2]

Conan: [00:50:17] But that’s meaning to me. I have so many people. We are a culture that idolizes youth beauty, and I am 58 and I am happier at 58 and I than I was at forty eight thirty eight twenty eight, 18 eight, you just like. And that’s my I. I just appreciate things more. I’m and I look back at myself and yes, I I think it’s appropriate. I you can’t. It’s very hard to be zen comedian in your 20s and 30s. It’s just probably not going to happen. But when people wax rhapsodic about youth, I think I like this better. I really do. And as you can tell, I work out a lot. And so I have the body of like a twenty two year old athlete. Sexual athlete [00:51:25][68.4]

Jameela: [00:51:26] Oh yeah. An ass that won’t quit. That’s what they say about you. [00:51:28][2.1]

Conan: [00:51:29] Well, actually, I have an ass that did [00:51:31][2.5]

Jameela: [00:51:31] However much they ask it. [00:51:33][1.4]

Conan: [00:51:36] Apparent.y, I have an ass that did quit and left because I’ve been told [00:51:38][1.3]

Jameela: [00:51:39] My ass never arrived and so at least at least have turned up to the party [00:51:43][4.4]

Conan: [00:51:44] My ass is in a FedEx tube somewhere. And I never got it. [00:51:46][2.2]

Jameela: [00:51:46] I’m Asian, I’m Asian. Mine just was never signed up for. For me, it was never in the cards. The storks just flew past me. [00:51:55][8.6]

Conan: [00:51:55] I, yeah, I was very disappointed when I was told by women that they were like, Oh, that guy, he’s got a great ass. And I think, wait, we have to have an ass. Yeah, no, I didn’t get the memo. So I’ve had implants. [00:52:09][14.0]

Jameela: [00:52:10] The expectation on men. It’s just it’s it’s so much, you know, especially us women. We can just chill. [00:52:16][5.6]

Conan: [00:52:16] Yes exactly. [00:52:17][0.2]

Jameela: [00:52:17] But you guys an ass and the bare minimum? God. [00:52:20][3.4]

Conan: [00:52:24] Let’s define bare minimum. And I want that in metric. It’s a it’s a more impressive number. Yeah, I have to say, I think that there is so much to as you go along and you just have raw experience. I have become much happier and I’ve done I’ve done work, which I believe in and I think people that listen to your podcast. You know, I think are very wise about this. And they’re learning about it, which is we all have these issues, and I’m shocked when someone doesn’t have an issue at this stage and more surprised or they’re not in touch with it, they just don’t know themselves. [00:53:10][46.1]

Jameela: [00:53:12] They’re liars. [00:53:13][0.4]

Conan: [00:53:13] Liars, but I think. Yeah, I like I like life better now. I wouldn’t change anything. I actually I would change one thing. I would take the knowledge that. [00:53:27][14.5]

Jameela: [00:53:28] your ass. [00:53:28][0.0]

Conan: [00:53:28] I would change my ass and I would add an ass where there is no ass. And I would take the knowledge that I learned from a sex therapist like eight years ago, and I would have that knowledge as a 20 year old man. I wish I. That’s the one thing I would do in time travel. [00:53:45][16.7]

Jameela: [00:53:46] A penile time machine. [00:53:46][0.3]

Conan: [00:53:48] Yes. A penile time machine. Exactly. There’s no better word for it than a penile time machine. [00:53:53][4.7]

Jameela: [00:53:54] How how it was penile time machine on your bingo card for any chance this year [00:54:00][6.1]

Conan: [00:54:01] Twice. Yeah. [00:54:02][0.4]

Jameela: [00:54:02] Ok fine, that’s good that’s exciting. [00:54:03][1.4]

Conan: [00:54:04] And both times, I insisted it be on there. I’ve I’ve been asked. I’ve been asked to leave many online bingo tournaments because I insist that that penile time machine be on there. [00:54:15][10.9]

Jameela: [00:54:15] So. So you’ve done so. You’ve done so many things. You’ve hosted your own show, The Tonight Show. You’ve you’ve hosted your own podcast. You’ve interviewed every you’ve interviewed fuckin David Bowie multiple times. You’ve you’ve kind of crossed off so many things that probably weren’t even on your bucket list because they were so preposterous. And and yet they’ve just kind of made it in. So so what? Like, what else do you want to do? You’ve got all this time left. We hope you’ve got all this time left. So now we [00:54:44][29.0]

Conan: [00:54:44] We have no idea. We really have no idea. [00:54:45][1.4]

Jameela: [00:54:46] But you know, you’re still relatively young. Fifty eight. So you’re nowhere near. I mean, Ted Danson is still going and he’s got 20 years on you. Almost. [00:54:53][7.4]

Conan: [00:54:55] Yeah but he’s Ted Danson. You know, he’s getting some special treatments. Some, you know, that are only available to Ted Danson. You know that he just looks too good. He’s getting some kind of special blood. He goes to some foreign country. [00:55:05][10.6]

Jameela: [00:55:06] I think you’re doing fine. I think. [00:55:07][1.4]

Conan: [00:55:08] There’s a Swiss lab, but [00:55:09][0.9]

Jameela: [00:55:09] What are the things that you want to do, not just career wise, but also like, you know, you said you’re still not good with confrontation, like what are the things that you would like to kind of spiritually achieve that you still like, haven’t quite gotten there yet? I really want to imagine that, [00:55:24][14.3]

Conan: [00:55:24] OK, I would like to care less what other people think of me. If I could have that part of my brain removed. I would have it removed. [00:55:37][12.7]

Jameela: [00:55:38] What do you want them to think of you? [00:55:39][1.6]

Conan: [00:55:40] Well, I’d like them to think of me as a nice person that tries. I try to make people I think instinctively when I’m around people, I try to make them feel better. So. And I just mean people on the street or people that I encounter, I I try to make their day a little better, but sometimes I think I. I think I’m too focused on it sometimes I think it would be a good idea to have a little more. What the fuck in my life? You know, does that make sense? [00:56:16][35.9]

Jameela: [00:56:17] I don’t know what you mean. No. What do you mean? I mean, I kind of know what you mean, but I want you to spell it out [00:56:20][3.2]

Conan: [00:56:22] Just like here’s what I’m going to do. I’m going to do this. And if people don’t like it, if I’m going to try this kind of thing or I’m going to try that kind of thing, and if people really hate it. Well, what are you going to do? I gave it a try and move on rather than obsessively worry. Does everybody like it do you know what i mean? [00:56:39][17.1]

Jameela: [00:56:40] Yeah I totally know what you mean. [00:56:41][0.7]

Conan: [00:56:41] I admire people that have I think I have a lot more of it than I used to do, but I’d like to keep going in that direction. Do you know what I mean? [00:56:49][7.7]

Jameela: [00:56:49] Is there a thing you have in mind, though, that you’re just like, I want to fucking try this, and I don’t care if everyone thinks you’re not, because are you worried that people will think you’re a bad person for this thing? Or are you worried that people won’t think you’re funny or they’ll think you’ve lost it? Like, what’s the anxiety? [00:57:02][12.8]

Conan: [00:57:02] Yeah, that’s the fear everyone has is that they stayed on the field when they when they should have gotten off. And that is especially scary in comedy because you can feel like it’s so easy to cross over into being, Oh my god him again. Is he still around? I’m so tired of his voice, and so there’s that. I think I would like to write something. I started out as a writer and I do aspire to write something and kind of aim high. And whether it’s my story or some silly fiction, I’d like to write something. I’d like to put pen to paper and write something and just put it out there at some point. That’s something I aspire to do at some point before I get too old. [00:57:54][52.1]

Jameela: [00:57:55] I think I’m going to hold you to that. I think that you should absolutely do that. Youre so, you have my favorite mind in the whole wide world, I’m I, I I fucking adore you. I know I’m really mean to you all the time. [00:58:09][14.0]

Conan: [00:58:09] Terrible to me, awful. [00:58:10][0.6]

Jameela: [00:58:11] But it’s it’s it’s it’s a bit because I love, you know? [00:58:21][10.3]

Conan: [00:58:22] We have kind of an S&M thing going. Yeah, you’re incredibly abusive to me. And I just I’m like, [00:58:28][6.4]

Jameela: [00:58:28] That’s why you wrote on the simpsons so. [00:58:32][3.4]

Conan: [00:58:33] I want I want more of that. [00:58:35][1.5]

Jameela: [00:58:36] No, I but I do. I adore you, and I think you are such a fine mind with such a sensitivity and such a heart and such a tendency towards the unexpected that I feel as though. And I know this is the exact thing that you’re fearing, right? I’m feeding into it right now that I’m expecting something really profound. I think that everything you’ve done has been a scary accident. You mustn’t lose that now. [00:59:00][24.5]

Conan: [00:59:01] Right I agree. [00:59:01][0.0]

Jameela: [00:59:01] I think this is the time that, you know, like, I know you’ve done a kind of like quite sterile version of your show where there’s been less kind of room for something wild to happen. Even doing this podcast, not face to face like, doesn’t feel quite as right as I want it to be. But it’s I’m so I know that you feel maybe a bit detached from that old side of yourself, but that’s where all of your magic has happened, is in the dangerous and in the unknown. And I would love to see something that you make. [00:59:26][24.8]

Conan: [00:59:27] OK. I’ll do something. [00:59:30][2.6]

Jameela: [00:59:30] I think you should do that. I really do. [00:59:31][0.9]

Conan: [00:59:32] I don’t know what it’s going to be, but whether it’s a clay pot or another show I’m going to, I like to make things. I’m going to keep making things, and I’m going to try and get better at if people like it, fine. If they don’t, we don’t live forever anyway. So. [00:59:47][14.9]

Jameela: [00:59:48] But also, it’s like yeah legacy and all these different things that I think hold us back, I think are so problematic and and if I may, failure. I have always and I’ve said this, I think maybe on this podcast before I prattled on to my poor listeners about it some other time. But failure, I think, is incredibly noble because it means that you tried when success wasn’t guaranteed. Like, I look at failure as something that is much more noble than just being effortless in your success. I really like I feel so, so passionately about it and I run towards it. [01:00:21][33.2]

Conan: [01:00:21] I think that’s true, and I think you also used another word which is, you know, legacy. And I think. [01:00:26][5.1]

Jameela: [01:00:28] Fuck the legacy. [01:00:28][0.3]

Conan: [01:00:29] Yeah, exactly. People get obsessed with this idea. I gave this speech once years ago. I think it was in 2000 at Harvard. They invited me to give a talk at graduation, and I told them about all my ups and downs. And that was in 2000 before I even had. I’d only had half my ups and downs at that point. But I told them success is like a white tuxedo. You become obsessed with, I don’t want to get any. I don’t want to stain it. I don’t want, you know [01:00:58][29.6]

Jameela: [01:00:59] That’s amazing! [01:00:59][0.0]

Conan: [01:01:00] And I said, You know it, it actually starts to if you have success, your fear of fucking that up can actually inhibit you, and [01:01:10][10.0]

Jameela: [01:01:12] mine is covered in blood and feces. And spaghetti and I’m sorry, I said faces twice on this podcast. [01:01:18][5.9]

Conan: [01:01:18] You’re a very you’re in the fecal zone. [01:01:21][2.8]

Jameela: [01:01:22] I’m going to take it back noo, I really don’t want. [01:01:23][1.6]

Conan: [01:01:24] It’s too late. [01:01:24][0.0]

Jameela: [01:01:24] To think I’m in the fecal zone. I really have no I’ve worked so hard in my life to not have you think I’m in the fecal zone. I only took the Good Place in the hopes that I could one day meet you and you wouldn’t think I was in the fecal zone. Truly like, I am sorry. So finish what you’re saying. I was. [01:01:42][17.4]

Conan: [01:01:42] Well, no, I was just saying that. I think I think that so many people are inhibited. They inhibit themselves, they build a cage around themselves with the success they’ve had, and then they think they can’t look any different. They can’t age. They can’t embarrass themselves. And we see that a lot in our business. And of course, you need to do all those things. We need to age. We need to embarrass ourselves. We need to try. We need to succeed and we need to fail and we need to get hurt. And as long as we are, you know, treating other people with some degree of, you know, kindness and compassion. Great. That’s what’s the harm if you’re not, you know, if you’re doing all that, why don’t you have the you’ve earned the right to fall on your ass a couple of times? [01:02:33][51.1]

Jameela: [01:02:34] Yeah. And I think also I want to look back on my life with a very, very stained tuxedo. I personally will look at that. And I mean, it’s already pretty stained. Anyone who follows me on Twitter, they’ve seen watched the stains happen in real time? And I’m sorry about that. But I I really like, I think, a part of the fabric of my life, I hope, is that I look back like it’s I want my tuxedo to be disintegrating. for the filth that I have acquired over the course of my life. [01:03:07][32.6]

Conan: [01:03:08] Yes, it should look like when we’re done, it should look like you jumped on a grenade to save your battalion wearing a tuxedo and it exploded and it’s just in tatters. You’re, you know, that’s what we should. That’s what it should look like. [01:03:19][10.9]

Jameela: [01:03:22] I really just want it to be nipple tassels. I really want it to have been reduced to just basically two nipple nipple covers. [01:03:26][4.7]

Conan: [01:03:28] Those little little pasties. [01:03:28][0.0]

Jameela: [01:03:28] Yeah. Little pasties yeah. So I just that’s that’s my personal dream is to run at failure is to stay on the, you know, to get that like not wanting people to like wondering when you’re going to leave the field. I want to be dragged off the field kicking and screaming. I’m just coming at this. I love imposter syndrome. When people think I don’t belong or deserve it, I’m like, Yes, I want to go in there. I’m going to get everything I can. I’m a good steal. I’m going to get some free meals. I’m going to take a selfie with Conan O’Brien. Like when I was on your show, the first time when I was there on my own, it was the absolute pinnacle and height of imposter syndrome because I’ve watched your show forever and I just couldn’t believe that I was sitting there with you on that show. [01:04:08][39.7]

Conan: [01:04:08] That’s so funny. [01:04:08][0.4]

Jameela: [01:04:09] Having that conversation is why I kept on as I was so inappropriate because I go into like, full [01:04:14][5.5]

Conan: [01:04:15] yeah, but you’re yet you were great. [01:04:15][0.4]

Jameela: [01:04:16] Worst part of my brain. [01:04:17][1.0]

Conan: [01:04:18] Yeah but you were great because that’s that is what makes it magical is you didn’t you [01:04:24][6.1]

Jameela: [01:04:26] Oh, went in there just like I was like, I don’t care what NBC are going to think about how this goes. I don’t care if the audience likes me. I’m going to make the absolute most of this. I’m not going to dare walking away from. I’m not going to walk away from this without knowing that I had as much fun as humanly possible just with you. I didn’t give a shit about how the interview came out or how I came across. I just wanted that moment. [01:04:44][18.5]

Conan: [01:04:44] That’s why it was great. That’s what makes it work. So let’s learn from that. [01:04:48][4.0]

Jameela: [01:04:49] So Conan, as I’m losing you shortly, will you just tell me, what do you weigh? [01:04:53][4.3]

Conan: [01:04:54] I weigh my moments throughout life of total freedom. Where I had no inhibition, just moments where I was making a group of people laugh or a bunch of people on the street laugh and I was just not thinking and doing and writing some kind of wave. And then there can be an audience there or not. But moments when I wasn’t afraid and I just did, and was happy that that’s what I weigh. [01:05:27][32.7]

Jameela: [01:05:27] I love that. Is there a particular moment that you have when you look back to that and you’re like, fucking hell, I felt amazing. Then there’s a kind of moment where you want to get back to that feeling. [01:05:36][8.8]

Conan: [01:05:37] I mean, I’ve had it. I’ve been blessed, but I’ve had so many times where I’ve just been in a room full of writers or with my wife and kids or at a party or any place, and it does not have to be clearly on stage. And I just started to. Unspool some weirdness in my head, and I had no fear, and I just went with it. And everybody’s laughing and then I’m laughing and I think this is such a nice antidote to all the worry and planning and anxiety and fearing, what will people think? It’s just such a great those moments. I live for those moments of just floating. And sometimes they have happened on a big stage, but more often they haven’t, and it just makes me happy for that. You know, fourth grader who was so anxious and so worried. You know, I can channel that kid at that moment and go, See, this is fun. It’s all good. Just. Anxiety is not your friend. [01:06:57][79.7]

Jameela: [01:06:59] 100 percent. Well, I am your friend. [01:07:00][1.0]

Conan: [01:07:01] Yes, you are. You are. [01:07:01][0.7]

Jameela: [01:07:02] Im going to I’m going to text you. It’s going to get weird if you haven’t written some pages. I’m going to need some pages from you. Conan ok I’m going to stay on you about that. [01:07:13][11.6]

Conan: [01:07:13] I owe you pages. And also we got to do a meal that’s going to be fun too. [01:07:17][3.2]

Jameela: [01:07:17] I would. I would die. I’d frankly die. And all of my all of the mess I got on my tuxedo has led me to being able to have dinner with someone that I adore so much. Thank you so much for coming on. [01:07:30][12.9]

Conan: [01:07:31] Thank you. I loved this. This was really fun. I feel like I feel like you could charge me now. This was a very good therapy session. [01:07:36][4.7]

Jameela: [01:07:38] Well, thank you for taking all of that depression and that pain and that anxiety and putting it aside to bring so many people so much joy for such a long time. And may you continue to do so. [01:07:49][11.2]

Conan: [01:07:50] I hope so. [01:07:50][0.4]

Jameela: [01:07:51] And now get the fuck off my podcast, right? [01:07:52][1.0]

Conan: [01:07:54] What a charming exit line. I love it. Thank you. Thank you for having me. [01:07:58][3.8]

Jameela: [01:07:59] I love you Conan. Thank you for being here. [01:07:59][0.6]

Conan: [01:07:59] Love you too. [01:07:59][0.0]

Jameela: [01:08:02] Thank you so much for listening to this week’s episode. I Weigh with Jameela Jamil is produced and researched by myself, Jameela Jamil, Erin Finnigan and Kimmie Gregory. It is edited by Andrew Carson, and the beautiful music you’re hearing now is made by my boyfriend, James Blake. If you haven’t already, please rate review and subscribe to the show. It’s a great way to show your support. We also have a bonus series exclusively on Stitcher Premium called Ask Jameela Anything. Check it out. You can get a free month of Stitcher Premium by going Stitcher.com/premium and using the promo code I Weigh. Lastly, over at I Weigh, we would love to hear from you and share what you weigh at the end of this podcast. You can leave us a voicemail at 1-818-660-5543 or email us what you weigh at IWeighPodcast@gmail.com. And now we would love to pass the mic to one of our fabulous listeners. [01:08:51][49.5]

Listener: [01:08:54] Hey, Jameela. I want to say that I weigh my recovery from a cocaine addiction and it will be 10 years in November, which is exciting, I weigh that I’m an artist, an activist and a cat mom. I weigh that my boyfriend and I have a healthy relationship and that he supports me and I weigh my anxiety, which I’m feeling right now because I’m nervous to do this at all. But I’m so excited anyway. And I weigh my depression and finally getting help for both. Thanks. Be well. [01:08:54][0.0]

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