Podcrushed - [Rerun] Conan O'Brien

Episode Date: July 10, 2024

Today we're rerunning one of our favorite interviews from Season 1! Conan O'Brien (SNL, Late Night, Conan) comes by to discuss his "need" for friendship and what it was like being the tall, lanky redhead in middle school in Boston. He also tells the group about the beginnings of his career in comedy at Harvard, SNL and more. Stick around to hear about his family's obsession with Gossip Girl and his thoughts on how the show ended.     Follow Podcrushed on socials: TikTok Instagram XSee omnystudio.com/listener for privacy information.

Lemonado Hello crushies, it's me, Sophie, here to tell you that we are taking a cheeky little week off from taping and rerunning one of our favorite podcrushed episodes ever, the one we taped with Mr. Conan Christopher O'Brien in New York last year. If you've never heard it, you're in for a treat, and if you have heard it, well, you're back for seconds enjoy gossip girl is obsessed with seasons so it's

always like well it's it's fall on the upper east side leaves are tumbling down and so are reputations oh my god that's great well you're right it's groundhog day in New York City

the groundhog saw a shadow but there's no shadow of a doubt that love is coming to Madison in 13th Street. This is Pod Crushed. The podcast that takes the sting out of rejection, one crushing middle school story at a time.

And where guests share their teenage memories, both meaningful and mortifying. And we're your hosts. I'm Nava, a former middle school director. I'm Sophie, a former fifth grade teacher. And I'm Penn, a middle school dropout. Okay, so let's get into what everyone wants to hear about. How do we make a tick?

talk i just want to stop i just want to shut down as i say that um no you know what's really cool the fact that we did anything in the realm of a skit with who i'm about to mention is is is a little insane i mean it's really bold arrogant it's arrogant maybe that we asked yeah but it's not because he's such a lovely guy i'm just going to go into talking about our guests a little bit we made a skit with Conan O'Brien. And it was real off the cuff, and he was encouraging. You know, and I want to say I was the one who asked him. Definitely, I would never have been able to.

And I, maybe too bold. Maybe a combination of bold and arrogant was why I'm the one who asked. And Conan said, sure, I'm a reasonable person. And that response really struck me because I was thinking that he, like, knew that it took courage to ask him and that there are a lot of people in his position who would say no. And I was really struck by that, that he, he, like, even kind of acknowledge it in his response. I would say that characterizes him in a lot of ways.

He, I mean, when I was on a show a few weeks ago, which isn't coming out for a little bit, but, um, because I'm real low on the, on the order priority. They've got everybody from... It's a holiday episode? Yeah. No, no, no, no, no. I'm not a holiday episode. I'm a January episode, which means, you know, you're just like, you just put them,

just put them up on the shelf. Um, no, no, Conan, uh, I would say, I don't know. It's just a lovely, encouraging person to be such a pillar of the world of public conversations in media, you know? I went into our recording session extremely nervous. At one point in the beginning of the interview, I picked up my water bottle and my hand was shaking so much that I had to hold it with two hands. I was so nervous. Yeah, exactly. But part of that was that, yeah, Penn and Navajo, you had met him before.

You had spent a little bit of time with him. And so. And we excluded you. Yep, I know. It's going to tell me a pattern. But this was my first time meeting him, and so I was really nervous. But he was incredibly warm and very kind to me. I felt like he could tell how nervous I was and probably could tell that that dynamic existed, that he had spent some time with the two of you, but not with me.

But he made special eye contact with me during the episode I felt like, and I think it was because he just wanted to make me feel comfortable. And I really appreciate that, just like very conscientious. The other thing I would say about Conan, and I hope this doesn't sound like a dig because none of it is a dig. He's obviously hilarious when you, like, listen to him and watch him on TV. But in person, it's funnier. Not funny at all.

No, it's funnier. Penn and I were reflecting on this when Penn did his interview. Like, of course he's so funny. He wouldn't have the career he has if everyone didn't recognize it. But in person, it's like to another level. And it's something about, I think, the way that he embodies it and the warmth. It's like somehow that part, you can't necessarily feel through a screen. But in person, it's like, I just was like, I don't think I've ever been around someone so funny.

Hey, guys, I have an idea. Why don't we just stop talking about him and start talking to him? Love it. Conan Christopher O'Brien is best known for his 28 years hosting late night talk shows. I mean, I've been watching him since I was 13. He's got his award-winning podcast, Conan O'Brien needs a friend, which I'm sure you've heard of. most recently his all Conan all the time Radio Channel Team Coco Radio on Sirius XM

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breaks the silence on August 19th. Follow us now so you don't miss an episode. Thank you for coming. Thank you for having me. I saw a bit that you did on Colbert. It was sort of of like a twofer. You talked about finding out that you were 100% Irish. Yeah, that's a true story. Yeah. That's really amazing. That's kind of rare, right? Yes. No, if you go to Ireland and genetically test everyone, you'll find that people are 80% Irish, but like 10% you know, Spaniard, but 10% Dutch. Everybody's a mixture of everything. And when I find out that I was 100% Irish, I said to the guy, who gave me the result I went is so that's good right and he said yeah like I got 100% and I know from my college days 100% is pretty good and he looked at me and he's like no I said what

does it mean he said it means you're inbred means you people are just a bunch of the Irish hillbillies that probably lived on the same farm and but yeah it's hard to do and I come from a long line of people who just married other 100% Irish people and would find them in central Massachusetts because we've been here since the Civil War. So that means that people were here in the United States where you could meet all kinds of people, but they were living in farm country.

They chose their cousin just again and again. Hey, I just met you in the bathroom. You must live in my house. Let's get married. It's convenient. But in the bit you talk about, you describe yourself as having a short tour. I'm not saying yes.

So describe that. Body shame Conan right now. You seemed horrified when I walked in. You did seem. I was like, oh, my, I was right. No, I have, I was very self-conscious. Okay, this is what I was getting to. Yeah, what was it like in middle school?

Well, one of the things that was difficult is that my legs were always really long. And so I always had what kids then called floods, meaning my pants didn't go down far enough. And I hated that. And so you could see, like, a lot of ankle. sock and ankle sometimes even some shin like you know what I mean it looked like I was wearing one of those

German when Germans go off to the countryside and they wear those leather shorts I mean it was ridiculous so my pants didn't fit and I hated that and kids used to make fun of like hey where's the flood was the joke back then

hey kid where's the flood hey Conan where's the flood I didn't like all the things that later on I came to be happy about I did not like I didn't like it took me a while to get really tall that didn't happen until later but I did not like my clothes I didn't like having an interesting first name and I didn't like having red hair I really didn't like having freckles I wanted to sort of look more like an Elvis Presley type I just wanted like black hair yeah and I wanted to

look more normal and I wanted a name like Jack Blaze you know I didn't want to be Conan and so there are all these things that just felt I felt allergic to a lot of my reality and then it's so interesting but that's the stuff later on that works for you and I think it's a blessing to be in touch with that later on in life I do think there There are people who have an awkward middle-aged experience, you know, middle-school experience. I've had an awkward middle-old experience. But they're people that have an awkward middle-school experience, and then things start to work for them, and they grow into their body, and they feel pretty good about themselves, and they

have success, and they actually forget or act like that other part didn't really happen. And I think it's good to remember that that part happened. and let other people know without mistake that that happened. That was a reality. And I felt, and because, you know, Penn, you know this, like our business is filled with people who are good-looking, successful, and because our society puts actors or comedians, you know, puts them on a pedestal, everyone's led to believe that,

that that is what they've always been. And they don't realize that, A, some of these people are miserable right now. Yeah. I mean, a lot of them are. Yeah. Or they're okay now, but they had a terrible, awkward phase

when no one was photographing them, you know? Yeah. Well, that is the spirit of the show in a way. I mean, I remember this period of life as the hardest. Right. Well, we talked about it. And it's so funny because, you know, when you first hit with Gossip Girl, anybody who was watching you then, any of the people that age would have thought

you are the dictionary definition of someone who's never had an awkward moment or a down moment. Which is funny, though, because I think you're right in a lot of ways, but I was still cast to play The Awkward Guy, which is so many levels of... Yes, but also awkward guy, meaning... On a TV show. Of a TV show. Everybody was in love with, you know what I mean? So it was, yes, you're right, but, I mean, I think if you had been able to tell what fans then at that time,

you'd understand five years ago, I was really in a bad place, and I felt really lonely, and, you know, my family was moving around, and I didn't feel like I belonged to any, whatever, they wouldn't know what you were talking about. Yeah. They'd say, what are you talking about? Yeah. No, completely. And that's the weird thing where the compounded pressure on,

middle schoolers and high schoolers is that that version a 20-year-old who'd been through it and was finally gaining some reprieve although to be fair actually some of the years during gossip girl the specter of fame always causes periods of intense discomfort i think for everybody at some point you know like it's you can go through waves with it but still yes i presented as together i presented as mature for a someone playing a teen i presented as all these things and yet i was still the version of of awkward so like kids who think that they're meant to look like this and act like this you know and be in these like sexy relationships and suave relationships every time you go to a party you're just like yeah I just got to throw on this tucks you're just wearing you're being dressed by other people you know it's it's something that I thought about a lot then and I think even that's the case with people who aren't celebrities like I remember feeling that way Wait, are we going to talk about people who aren't celebrities now? No, that's not we are a podcast for me.

No, no, we, Mike. I think his hours up. Excuse me? Was this not in the writer? We are not talking about, why the fuck would I talk about regular people? Why did you bring me here? Excuse me, Penn, you were talking about being really famous? Jesus, let's keep this thing on track.

Let me talk about gossip. Anyway, go ahead. Yeah, I remember feeling that about my friends, and, Recently, I reconnected with a friend from high school, and we had fallen out, and I couldn't remember why. And so I just reached out to her as like, what happened? Why did we fall out? Big mistake. Never write somebody from years ago and asked why you fell out.

No, it actually ended up in a really sweet connection between the two of us. But one thing that we realized was we both felt like the other person was so confident, so, like, aware of themselves, and sure of themselves. and we needed to take time apart from each other to be able to feel that on our own. But we both felt that about the other person and we just never talked about it. I think that's the thing that's exacerbated now by social media

and is that everyone's always putting out there the best version of themselves. So everything's curated. I mean, photos are curated. Experiences are curated. No one's posting just got done. or I'm here in a bad restaurant and they won't wait on me

or I everything is a peak that's what TikTok is for yeah exactly everything's a peak moment everything's a peak experience and so naturally when people scroll

they get depressed because they are having this this sense this FOMO this sense that everyone else is living this amazing experience which isn't true I still feel

I mean, being so conscious of that doesn't help that feeling, by the way, which is interesting. I feel like when I get on social media, I'm immediately plunged back into that dynamic. I really imagine everybody being better than me. And it's like, that's not how I feel all the time. It's not just now. It's like that. You usually feel like you're better than everyone else, right? Generally, generally speaking.

That again, Penn and I are on the same page. We both think we're the best versions of a human being. There's also this other weird thing that's happening. You're 100%. I'm 100%. So you are in a way. There's also this other weird thing that's happening where not only are we comparing ourselves to the other people we see on social media, but we have created now over the last 10, 15 years, this archive of our own lives, and a lot of it is not real. Like if people are using filters, if they're editing their pictures, and even if they're not doing any of that, if they're just taking pictures of the most beautiful moments, the times when they're the happiest, then when you look back on your life, you're comparing your current state.

to a state that doesn't actually totally exist in reality. Do you have that thing where on your phone, I have an Apple phone and an iPhone, and you won't expect it, but you'll just get up in the morning and you brush your teeth, whatever, and then you grab your phone, and it's curated this little music video for you of your life.

Memories. It's amazing, actually. And it is absolutely amazing, but I'm not ready for it ever. I'm just like, you know, I just got out of the house. house and I'm going to, okay, and I'm just going to look down up my phone and all of a sudden I hear this incredible song, like you know, sound of silence or something.

Hello, darkness, my old friend. And I see, oh my God, I'm in Bermuda. I have come to a pumpkin with you. Oh my God, my wife is beautiful. There's a softened coffee eating. Oh my God, my children are so young. We're making, we're carving

pumpkins. And I'm not ready and it's this huge emotional rush and I think there's no lead-in. She was so interesting. There's never, and I'm, I just always put it the phone down and go, like, that was, I guess it's over now, but it was a great life. Exactly. Conan, speaking of things you're not prepared for it, we actually dug up, actually one of our producers dug up a clip that we wanted to play for you. Let's listen to this.

Hi, I'm Conan O'Brien, and here we are with Kate O'Brien, the softball star. Hey, Kate, how you doing? Pretty good, pretty good. Hey, Kate, I understand you're on the softball team, your freshman year in high school. Yeah, I was. I was out there in the outfield left center. You know, the whole bit. What do you consider your specialty in the field?

Just about everything. I hear you're pretty good. Oh, a lot of people have heard that, you know. They've heard it mostly from you, I hear. No, that's incredible. That was from, man, I would be, I'm going to say that's early 1970s, and I'm probably, I don't know, 10 years old or 11 years old. But I do sound like a kid who grew up, or who's a child in the depression. You really do.

You'd actually discover time. The tape quality sounds... Yes, I know. I know. It's ridiculous. It's amazing. And I'm being a little wise guy, and I'm working on my timing and my patter. But, yes, that's a great clip to play because that guy doesn't know what he's doing. You sound being very confident.

But I love the little laugh at the end. That was my favorite, the little ha-ha. What do you went back to? Yeah, they had mostly for me yourself. That's me putting a laugh in case there is no laugh. Yeah, yeah. It's your laugh truck. You know what I should do?

I should have done. I should have done that throughout my career whenever I made a joke. But if you ask me, that's more like Bill Clinton. Nah, just in case there was no laugh. So you were interviewing your younger sister. Yeah, I have two younger sisters. That's Kate.

I have another younger sister, Jane, but that's just me doing a stand-up interview with my sister Kate, who was quite athletic. And so I was interviewing her about all the different sports that she likes to play. I love the banter between you, too. Yeah, you know what's nice? my brothers and sisters are really funny

I think they're proud that I've had this success but they don't really care and all of them put me down all the time in a good way that's healthy yeah well I think it's burges on abuse but it is healthy

and my kids are like that they're just they roll their eyes my career is I think on some level they're proud of it but it's not a big part of their life or their world and when I do something ridiculous they let me know how stupid that was

and I think that's good it's just this loving gravity it's a kind gravity that just keeps you like a weighted blanket from spinning out of control my siblings are like that too they definitely keep me humble but you were one of six

what was that like growing up one of six did you do a lot of stuff like that with your siblings yes did a lot of we did a lot of a lot of fake fighting I used to love and real fighting but a lot of fighting with my brothers

and a lot of people giving each other a hard time there was not a lot of and this is probably very typically Irish Catholic but there's not a lot of direct you know can I talk to you for a second you kind of hurt my feelings when you said that that none of that happened

it was everything was done with sarcasm and humor and I learned that that was the way to communicate with people was joking around and kind of letting them know that you're unhappy but if they called you on it say no no I'm just what are you talking about I'm just kidding I'm fine And so, I'm not saying any of that's healthy.

I was like, and how about now, you feel that's saying? But if taken to an extreme, you can monetize it. Which is true of Ben. Clinton has advice for 12-year-old. Yeah, which is true. Hey, you 12-year-olds out there, if you're feeling a lot of emotional pain, remember, take that to an extreme and you can monetize it and be an unhealthy person in show business. Conan, I want to ask you a middle school question just that we haven't gotten to.

Which is when you had a crush on someone, what were you like? And could you tell us about your first love and heartbreak? Well, there was this girl in fifth grade that I had a huge crush on. And her first name was Laura. And I just was, I remember her last name, but I feel like if I out her, you know, she might say you creep and accuse me of stalking her. you know, 50 years later. But her name was Laura, but I remembered my skin temperature would change

when she was around. You know what I mean? You feel like you're running a little bit of a fever. And I don't think she ever really noticed me. And then I remembered she got a little got a little gothy later on, which I thought was even cooler. But years later, I think when I was in college, she did not go to the same college,

but I saw her once, like, in an outdoor cafe, and she said, oh, hey, Conan. And I was like, oh, I'm really like my voice crack. She's like, oh, Conan, your voice hasn't changed, but you're 40. What's going on? But I remembered very much being, and not knowing what to do,

and I was a late bloomer, so not having, I mean, I, you know, didn't start dating until later and you know i was not there were kids i remember there were there were kids when i was 12 when i was 12 i looked 8 when these other kids were 12 they had to shave like twice a day and they were just confident in how they walked and with their bodies and they had girlfriends and um he were like what how is that how am i even the same species is that yeah He's my Check, you're my

How old are you again? I'm 12 I'm 12 Why? Yeah I'm 12 too What are you? I just saved 10 minutes ago But you got a full beard

I know Yeah I gotta go drive a truck now Drive a truck You're 12 Yeah I remember I used to teach fifth grade

And I had some students Who would like Bring in stuffed animals Into the classroom And then some who were like Dealing weed You know, like, it was like, really...

Was that you, Sophie? Were you the weed dealer? Yeah. No, but I think that... No, just for legal purposes, it was not me. The disparities then are mind-numbing. And then there are kids who are just ready for things and other kids that aren't ready for things.

And, you know, I have two kids, and I remember my goal for them, and I would talk about it with my wife, was I'd like them to grow up slowly. Like, our job is to make sure they grow up as slowly as possible. Yeah. I love that. I love that.

I love that. I love that. I love that. possible. I want them to be kids for as long as possible because all the other stuff will come the disappointments and different kinds of pain. But let's just see how long we can I want them to be giddy and excited about things in a youthful, childish way for as long as possible. How old do they know? They are, my daughter is 19 and my son turned 17 today. What's his name?

His name's Beckett He's not going to hear it today But happy birthday Beckett Yeah And he very much I've never missed a birthday of his But And that's a pact we have

And I said I can't be with you today Because I need to go to this podcast And he said Is it a podcast you could do another time And he said Absolutely not I said I told Penn

I told Penn Bazzar I do it And he said, you're clearly joking, and I said, I'm not, and I'm leaving you right now. So I flew here, and my wife says that he's despondent and won't come out of his room. And the purpose of your podcast is to help children, my son's age. Only on the surface, Conan.

Only for the numbers. The irony. It all comes down to the bottom line. I flew here at my own expense. We all work for serious. Okay. No, but it is fun. I mean, that's a whole other experience

when you have your own kids. And I know you have gone through this. I don't know if you guys don't have any. You've not crossed this Rubicon. If you know anyone nice, Conan, please let me know. To be your child. Are you to adopt you? Yeah.

Oh, okay. I thought you meant to you know any nice people that want to be your child. Stick around. We'll be right back. All right. So let's just, let's just real talk, as they say for a second. That's a little bit of an aged thing to say now. That dates me, doesn't it? But no, real talk. How important is your health to you? You know, on like a one to ten? And I don't mean in the sense of vanity. I mean in the sense of like you want your day to go well, right? You want to be less stressed. You don't want it as sick. When you have responsibilities, I know myself, I'm a householder. I have two children and two more on the way. um a spouse a pet you know a job that sometimes has its demands so i really want to feel like when i'm not getting the sleep and i'm not getting nutrition when my eating's down i want to know that i'm

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I think it tastes great. I use the liposomal glutathione as well in the morning. really good for gut health and although I don't need it you know anti-aging and then I also use the magnesium L3 and 8 which is really good for I think mood and stress I sometimes use it in the morning sometimes use it at night

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A question that we love to ask, anyone who comes on this show, is to share an embarrassing story from middle school. Do you have any that you can share? Have any. That's like, can you narrow it down at all? I'm trying to narrow it. I'm trying really hard to narrow it down. I remember in middle school, I was very interested in comedy. I was very interested in performing.

And so a friend of mine and I, I'll shout him out, Jake Fleischer was my best friend. And we decided we were going to write a play. And it was actually a musical. Now, we didn't write the music. We just took existing tunes and wrote different lyrics to them. So you wrote the pilot of glee. Exactly. Yes, we did.

And I'm still suing the glee people because I think they ripped me off. So we did this, we wrote this play. It was so ridiculous because my friend and I, we wrote this thing about two guys who are down on their luck and they meet up and they're like, hey, I like the cut of your jib. And the other guy's like, yeah, you look like you've got the skinny.

Hey, let's form up a team. You bet, we're going to do the best. You know, whatever. And it's like, you know, the year was 1974. or something and we're writing this bullshit thing that feels like it's from 1920. But

that was not even the embarrassing part. The embarrassing part is we had a very supportive public school and they said, you know what? Conan and Jake, they wrote this play and it's got music in it. God bless them. We're going to let the whole school come see it.

So big school, this is the Michael Driscoll School in Brookline, Massachusetts. Big auditorium, everybody got out of class to come see this play. Like a special performance. It wasn't a talent show or anything. It was like, you know, hey, some kids wrote a play

and it was just the two of you. And it was just the two of us. Jake and Conan. I'm not even at the embarrassing part yet. This is the best part. So we go to the whole school's there and I remembered us being backstage and you can hear the crowd out there

and this is exciting. And so it was a two act. You know, there was one act, and then the curtain comes down, like, we're going to give it our best shot, dump! The curtain comes down, and then you see what happens when we fall from Grace in the second act. Keep in mind, again, the whole play is maybe 18 minutes, so we're out there for nine minutes in the top,

the curtain comes down, the curtain goes back up again, and we do the second nine minutes, and that's the show. I had just recently, for the first time, been to New York, and someone, my parents had taken me to a Broadway show, And I, like a total ass, timed the intermission. It's 25 minutes. And so I remembered very clearly talking this down the day of the show. And I said, right, the curtain will go down after the nine minutes.

And then Jake said, yeah. And then we'll just, you know, change to our different hats. And the curtain will go right back up again. And I went, no, Jake. A true intermission is 25 minutes. And he went, what do you mean? I said, it's 25 minutes. Jake had some sense.

We had no scenery. We had no costumes, really. There was no changeover. Nothing had to happen. But I was such a dick. I was like, I'm telling you, I've been to a Broadway show. So we did this nine minutes bullshit thing. The curtain comes down and kids are out of school.

They're happy. They're like, hey, all right, whoa. We're backstage. Five minutes. Ten minutes. And you can hear. like people are thinking what is going on and then 25 minutes curtain goes up and people were pissed I'm amazed they stayed you're pissed too yeah they had to stay and so afterwards we're like

thanks everybody you know and then we're wandering around the Michael Driscoll school playground afterwards waiting just to be congratulated and I remember kids coming up and they were like, what the fuck? What were you doing for 25 minutes? And I said, it's called an intermission. It's show business, maybe. And then I remember teachers coming over and going, can I quit talk to you for a second?

What were you doing for 25 minutes? Nobody came up and said, like, listen, kids. I think they, like, no one knew, and it was, there was very much, like, well, we assume that they're building this incredible set. They're doing something, and then comes back up again. and we've done nothing.

Nothing's done. It's like if we stop this podcast right now and I said it's time for the admission and we just sat here like idiots for 25 minutes and then came back. And so everybody was mad and to this day. I just can't believe.

I was that stupid. Did you have to like force Jake back from... He was like, Conan, we got to pull the cord, man. I'm telling you. Exactly. No, Jake, to his... credit and I've I've encountered Jake many times since then and again shout out to Jake Fleischer who also survived this terrible calamity but he was like come on let's just go now it's been 15

I said 25 are you want to be in Broadway or not were we yeah I was so I was an incredible but look who came out victorious well I was going to ask you did did that continue for the rest of your childhood your interest in performing yeah I was always interested in in it but i did think um you know i lived in boston and i don't we were we felt like a thousand miles and a thousand years away from show business there was just no encounter with show business so i i wasn't around people in show business my parents are professionals my dad's a you know research uh scientist my mom's a you know lawyer they're serious people and so i was very interested in it and then said well anyway i'm gonna i want to make something of myself so i'll

I'll just buckle down in school. And I was highly anxious, kid, but in a good way, channeled it into, I'm so worried about doing well in school that I was a grind, so I studied a lot. And that ended up in a crazy turn of events enabled me to go to a really good college that happened to have a hero magazine

that was the oldest and most famous humor magazine, in America, the Harvard Lampoon. And so by trying to give up this dream and work really hard to be a serious student and go to the big school that people want to go to and be serious, I ended up a week after showing up there. Someone said, you should go check out the Lampoon. And I was like, the Lampoon, all right.

So I went and checked it out. And got in first semester freshman year, which was a bit unusual, and then bang, that changed my life. then I was all comedy all the time so my best efforts to not pursue this led me right back to it so when was your

going sorry go ahead in your lowest moments in your career did you ever regret it where you're like I wish I had done this like other standard path or have you always oh god no no I always I always knew I was doing a it was when I was first a writer for Saturday Night Live in 1980s

And I was a young lad and this writer strike, I get hired at SNL, the dream job, so excited. I do a couple of shows and this writer strike hits. And so suddenly Bob Odenkirk, who was a writer that I shared an office with and Robert Smigel, they said to me, hey, Conan, we're going to go to Chicago and just do like a silly show of sketch. is that would never make it on SNL, you seem like the kind of guy that would want to come with us, you want to do it, and I said, yes, I do. Right up your alley.

So I remember doing this show at the Victory Gardens Theater in Chicago in 1988 called Happy, Happy Good Show, and reviews weren't good, audience was tiny. I had a terrible car. I had a 1973 Plymouth Valiant. I had no air conditioning.

It was really hot that summer. I was always hungry, just because my metabolism was crazy and I remember being very physically uncomfortable all the time but the fact that I was doing this show I remember thinking I will do this for free before anything else I've never ever ever thought

you know law school would have been good for me I think I would have been a terrible lawyer so what were you trying to you said a moment ago giving up the dream So when did that dream form and then when did you feel like you had to turn away from it? I think the, the, I was very interested in show business and I was one of six kids and I would, we would see old movies would come on and I would watch them and I would think, oh my God, I want to be like a showman. I want to be, that looks so cool. And so I asked my parents, again, all my ideas about show business were incredibly out of time and incorrect because it's the 70s.

Some cool stuff is happening out there. And I was like, you know what? I'm watching movies from the 1930s where people tap dance. So I told my parents, you know what, I'm kind of interested in show business. I need to learn to tap dance. Guess what? No, you don't. You don't have to learn.

Led Zeppelin is on the chart. No one's tap dancing in Led Zedk. Yeah, I know. But again, I was wrong. But I went, and to their credit, they found me this really old, wonderful man who taught tap dancing near the Berkeley School of Music in Boston named Stanley Brown,

who had learned from Bill Bojangles Robinson. Wow. He was this old, like, I want to say 70-year-old black man and all of the people there, everybody was black, except me. There was this one orange-haired boy who looked like the Wendy's logo. And I would come in and I'd be like,

hi, everybody, got my shoes. And they'd just be looking at me. You're like, this guy. And like these incredibly sexy women who were doing modern tap and jazz tap. And I'm like, hi, everybody, do anyone have a cane and a straw hat? You know, one, two, shuffle off to buffalo.

And so I, but I was perceived. suing that and then I think at some point I want to say probably around sixth grade I just thought what are you doing there's no you know is that something you could pull out of your back pocket now like if someone did you do it for tattoos not really I know I know a step or two but not really and uh um no it was you know I took tap for a moment I was like I think I think there should be a tap off yeah exactly and nothing there's nothing better for a podcast than a dance off you're just going to hear people going like tap it tap them taping right now

this is incredible right now I'm imagining Conan Wright are tapped testing in this studio but you can't say it The pen just took it up a notch

no no no Conan's in the lead now Penn This is sounding like F1 Yeah Backflip Front flip So how do you feel

In terms of your I don't want to say career but in terms of this craft that you've been developing for decades now Right you I think very much

are a case of evolution because look I've done I was never on your show I wouldn't allow you on remember we had a you know the way if someone passes a bad check at a supermarket they put up a picture of them

and say this person is not of that we had a picture in Rockford's Center and Baddian said this man is not to be allowed on the late night program and it's because he passed a bad check at our show so it all comes back around

But no, it's funny because we, you know, we managed to just pass each other but never really connect. I don't know. I mean, I think I wasn't quite in a, I didn't, look, I was on your show recently and I didn't feel worthy then. I mean, this goes back, this is why we have a show about middle school exploring the ideas of self-worth. But anyway, this is not about me not being on your show. What I was interested, we can talk about that more. That's right. For reasons of criminal trespass.

Yeah, which I kind of like the ring of that. But you now are able to do something in a format that was just simply not available. Yeah. Or feasible. It wasn't interesting. It wasn't marketable. And you are, you know, like amongst one of the early adapters, as we say in the realm of podcasting. yeah i think we say um i just loved being able to be on your podcast and to speak for um because

i just love speaking at length as we can see it was great we know about this no no he did a six hour podcast i didn't get a word in edgewise i believe it how do you feel about how your your ability to evolve this format and and to well first of all i feel very fortunate that there was people working for, you know, 15, 20 years on podcasts, you know, trailblazers that started this thing. And what I feel really fortunate about is that, and it's total luck, but I had some really smart people around me five years ago who said, you should do a podcast. And at the time, I was thinking, well, I have a TV show. And so why would I do a podcast?

And they said, well, just, why don't you do this? Why don't you just go down? We've set up a microphone and screw around a little bit. and I had a blast. And so that's how it started was just trying things. And so one of the messages that I've tried to impart to younger people is you're not penalized for failing as much as you think you will be. Clearly, if you try to jump a canyon and you don't make it,

the penalty is quite high. But for the most part, I try to encourage people in middle school and also people in high school, college, we have this society that can be quite forgiving of screwing up. So you can try things and they don't necessarily work out. But you'll learn a lot. And I think having that philosophy has helped me a lot because a bunch of things haven't always worked out,

but you just keep throwing things out there. You keep trying, keep moving, keep trying to evolve a little bit. And people tend to remember you for the things that do work. I like that which is nice I think you're remembered for most often you remember

someone told me years ago it's this brilliant Simpsons writer named George Meyer he said I think people are remembered for their good work it's not like people walk around and recite

you know man that they just when they talk about Herman Melville they talk about you know Moby Dick they don't talk about oh my god you read that third book

the one that's about the cracker you know the salty cracker that's terrible They don't talk about that. They talk about the good tends to stick in people's thoughts and minds. So why not try? Why not try a bunch of things and don't sweat?

That's so encouraging, Conan. It is. Do you think that's true in middle school, however? It does seem to be a bit inverse. Well, the thing in middle school, I think, is people feel like everything matters. Yeah, you're hyper aware. You're hyper-aware and you're so self-conscious. And so you think, oh, my God, I just destroyed my life.

I just destroyed my life because I embarrassed myself in front of the class or I screwed up and I'm done. And I remember feeling that way all the time when I was young. Like, I am done. Yeah. I remember, you know, I'd be like, there are 15-year-olds. You're like, well, it's over for me. I remember I knew a kid in middle school who thought that he had peaked in fourth grade.

And it was like, and it was like three years later and he was like, remember me in fourth grade? And I say like, yeah, he just thought that he had hit it. He was really cool. He was new to the school. Everyone thought he was a great guy. And then he thought, yeah, fourth grade. Oh, my God. To think that that was your peak.

Yeah. And I think somewhere, I swear to God, this kid, this guy now is my. my age is wandering around telling people fourth grade. She's seen me in fourth grade. Fourth grade is a good year. I like the mission of this podcast because I think I try to be very honest with people about awkwardness and I think it's been a big part of my career and various difficulties and seeing the humor in it.

But I think kids, I call them kids, but middle school, kids that are middle school age get it incredibly they're bombarded with so much and they do the biggest mistake is they don't realize that other people are feeling the same stuff that they're feeling they don't understand that other people and that people you know grow and mature at different rates and so it's really fascinating to me to see um all of this wisdom does come with age. I know we have a youth-obsessed culture, but I do think that when you're around longer, you do start to understand things that you can't understand in any other way than just being alive, you know, long enough, which kids don't have that perspective.

It's totally true. So our podcast is called Pod Crushed with the ED, and the reason sort of initially was our idea was like, let's take the sting out of redaction. It looks good on my T-shirt. Yeah, it just looked better than Podgraf. No, like, take the sting out of rejection, like send us your stories of like a time in life that you were like crushed by something because that's universal and you'll get past it and one day you'll even like laugh about it. That was like our initial premise

and I think that we've seen that it's true no one escapes it and also sometimes that's like character building and it's actually a point that we have those moments. I think a lot of it is confidence and confidence comes with time. Now as I said earlier some people have it at a very early age

but it took me so long to build up my confidence. Yeah. It just felt like it took forever. Yeah. In middle school, I don't care who you are, you need something. You don't know what it is other than attention. Maybe you call it love, but you're probably not comfortable with that word.

I'm still not comfortable with that word. I've never called it love. I've been 77 years old, and I'm not comfortable with the concept of telling someone I love them or I need love from them. I was like, wow, you look really good for 77. It's a ton of work. after. When Penn first met me, he was just stunned by the amount of work I've had.

And how bad it is. He could tell right away, yeah. I went for the least expensive. You can't beat this guy's prices. So that's where I went. $1,100 to get your face completely recut. Yeah. So, yeah, well, you know, first of all,

I'll tell you the title of my podcast is Conan O'Brien needs a friend. That's right. Which is a joke, but also not a joke. Yeah. but also a joke, so it's one of those things that just kind of flips around. But, you know, it's interesting because you're talking about this period of life, you know, middle school where you don't realize it at the time, but you're only like half cooked at that point. You're like if you took a muffin out of the oven after six minutes, it's not, it wouldn't be batter anymore, but it's not a muffin.

How long does a muffin cook for? Well, it depends. Your altitude. That's not the point. Sorry, I do a lot of my baking at the top of Machu Picchu, where it takes up to nine hours. But yeah, people are not, they're not formed yet. And when I look, I remember very clearly in middle school thinking,

this is, I guess, who I am and being very dissatisfied with it. And not understanding that, no, no, no, no, no, no, no, no. you've got there's you're so long you takes so long like now i just turned 36 and i feel like i'm honestly just starting to really lighten up right you know right i've heard 40 is even better well i got some bad news for you uh no no yeah but see the thing is you're all very young and um you are going to still keep evolving that's what people don't realize is that there's this evolution that happens that continues. So I think that I'm somewhat mellower now than I was even 10 years ago when I'm by the definition of anyone in this room. I was

old then, you know, I'm 59. So I still think I was forming in my 40s and into my 50s. Like it just takes a long time. That's very hopeful. The other day I had this realization. Actually, I was watching This Is Us. I was watching the finale and I don't, you know, it gets a little cheesy. It's a little cheesy. But I realized like I'm 28

and I can sometimes feel like I am put out to pasture. Like it's over is it over for me. I'm on the cusp. I'm like, I'm 94 and I think 96 is Gen Z. So it's like, you know, cuspy. And yeah, I just find that really hopeful.

That there's so much that happens throughout life and that you continue evolving and that it's not over in middle school. It's not completely hopeful because what happens soon as I'll start de-evolving, that's the problem. I'm going to start losing. So where's that peak moment?

I am two years, I think right now, I'm two years into de-evolving. I think my peak was like two years ago, and now I think it's just, I can't come up with that person's name. it just took me an hour to urinate. We don't have to get specific. Can we go?

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and start listening today so I know because I was able to sit in on your interview with Penn that you were a gossip girl Stan and I wanted to know I feel like Conan was a Stan well what happened was I my kids discovered the show

the original show like two, three years ago and we just started, it became, that would be the thing that we would all watch together as a family because it was kind of fun and there were elements of the show that, you know,

the whole Chuck Bass character was so hilarious to me and to my kids that this person who's basically like 15 years old is drinking a scotch, drinking a scotch and wearing a smoking jacket and telling a man in his

50s, you're through at best industries. I bought out your controlling chair. I bought out show a controlling chair 15 minutes ago and the board has seen you out. Good day to you, sir. You're done. There's a plane waiting for you on the tarmac. You're like, what?

I can't do that now. I, you know, but I, so we started watching it and then I never do this. I never do this because I get to interview all these, you know, really cool, great people. I never asked, but when Penn did the show, I said, I hate to do this, but can I get a selfie with you?

No. And tell him what I said. What did you say? No. He said no. Wait, really? And he shut me down. Yeah.

Did you not take a selfie? No, of course. No, no, no. So I said, I never do this, but can I send, can I take a selfie with you? And he was like, oh yeah, sure. Of course, he was really nice about it. And I took it and I sent it to, we have a group chat for our family, which is just my wife, myself, my two kids.

and I sent it and they were all flipped out of the you know and it's just funny because it's I like it was just this moment

of that's been something we've bonded over so it's really fun I think as a family you should start watching the one where I put people in cages

you know once Beckett graduates yeah yeah anything that encourages people to masturbate in a public space but I did want to ask you

So as a gossip girl fan, what did you think of the reveal that Penn Badgley slash Dan Humphrey was Gossip Girl? Well, thanks for the spoiler. Did you know that? No, I did know that. I was like, oh, no, they ruined it. No, I did know that. The only thing it blew my mind is it's not something I saw coming, but...

No one did. But... The writers didn't know. No, no, trust me. Also, if you go back and look at all the episodes and try and see how someone would have... Yeah, it's not possible. It is not at all possible.

So I just thought like, okay, I see what they, you know, they were in a corner and so why not? They wrote their way out. They wrote their way out. You have to. I mean, what show is in that position at some time? Yeah, exactly. But I think it's cool that you go down. Actually, I agree.

Like, as a person who is somewhat transparently, publicly, maybe inappropriately sometimes shared about the resistance and the conflict I had of being on a show like that or just always. just always kind of being in the public eye I think it's interesting that I am I'm gossip girl I take that as like a I thought it was I think it's a cool move

and it's just I encourage people not to go and look through all the episodes and try and make it line up yeah because there are times where gossip girls like well if you ask me and like no no you're not even you weren't there for that that's the episode where you're trapped in a mine

in Mexico and you know X-O-X-O X-O you're like no you what you tweeted that from the mine now people are going to go looking for the episode you're trapped in a mine

part of me wants to just for the just for the enjoyment of the real stands out there to re-record the Gossip Girl voiceover which you know Kristen Bell did

so iconically but it's interesting that I've now done you know a somewhat comparably iconic voiceover show like this show that I'm on now and then to do Gossip Girl in my voice

I think you do it should we do it right now? I mean if they have $10 million. He's got to get paid first. Well winter came early to New York but the real chills on the Upper East side. Oh that's a good one! Oh trust me they love their they always take Gossip Girl is obsessed with seasons

so it's always like Well, it's fall on the Upper East Side. Leaves are tumbling down, and so are reputations. Oh, my God. That's great. Well, you're right. It's Groundhog Day in New York City. The Groundhog saw a shadow, but there's no shadow of a doubt that love is coming to Madison in 13th Street.

That's too low. It's too low. No. That's at the mine in Mexico. My other favorite observation about Gossip Girl is that the parents are six years older than the children. That's always my favorite thing is you're like, wow, I've got to go ask my dad, you know, hey, Rufus. And he's like, hey, son. I'm like, wait a minute.

That guy's 29. You're 23. When did it? I remember when I had you when I was six, it really makes me, it really makes me laugh. The parents are all incredibly young and fit. Smoldering. Yeah, and it's kind of confusing, like, wait a minute. Who's the father here and who's the kid?

Yeah. We ask everybody, so you're not special. It's just getting intense. Yeah. If they could give us some money. If you could go back to your 12-year-old self. Yep. What would you say?

What would you do? More sunblock. would be the person I would say there's a thing called skin cancer and you were a ticking time bomb I would say you know it's funny because

they do encourage you in some therapy to really picture yourself at that age and what would you say to that person and mine would be it's going to be good it's all going to be fine you're freaked out right now

you're anxious trust me things get better it's going to be okay and I would have loved to have heard that if I could have appeared to myself I would have been you know the kid would have been frightened when did I become an older woman

do you comb your hair up like that on purpose you're missing the point I'm coming to you from the future. What is that hairspray? Did you put hair spray in your hair? Why would you do that? Listen, quiet. You're missing the point.

I come from the future. Wait, Trump becomes president? Isn't he like a real estate? Shut up! I'm not here long. I don't have much time. I don't have much time. It's going to be okay.

Yeah, so what? I don't think it's going to be okay. I'm looking at you and you don't look okay. I'm medicated. Why are you medicated? There's depression. I think if I showed up in person to my younger self, it would go terribly. I mean, it would end up bickering and yelling at each other.

But, yeah, the core message and the core message to young people listening is it does get better. And everything you're feeling is exactly what you're supposed to be feeling right now. And that's just the way it is. and just onward, it will get so much better. That's what I say. Of course, a bunch of young people listening right now are like, I like things now, Dord. Shut up, Conan.

What's wrong with Conan? I don't relate at all to his childhood. I know that an intermission is not 25 minutes long, especially if the show is only 18 minutes long. Thank you. Thank you so much for having me, and this worked out really nicely because you came on my podcast in Los Angeles, and I always try to leave town when it's my son's birthday, at his request. This is my gift to my son. Today's listener submitted middle school story involves a toilet.

I'm actually surprised that it took us this long in a show about middle school to include a toilet, but it's a good one. Stick around. Oh, shit. I think you've got to keep that. Yeah, for sure. I'm from Tamil Madhu, South India. My family, like a lot of middle-class families in my culture, were against me dating anyone. So I had to hide all of my relationships from them

and sneak out all the time to meet my boyfriend. I was in a relationship with this guy for my tuition, just extra classes, coaching is very common in India. It was new, and everything was exciting, especially because it was a secret. So there was this old, unfunctional toilet room outside my tutor's house where my boyfriend and I would make out, and this kept going on for a while,

until some auntie figured it would be a good idea to store some old stuff in this place. So one day, she tried opening the door while we were inside. The door was never locked, and there was no reason for it to be now, so she got really suspicious and starts knocking and asking if anyone is in there. Obviously, we didn't answer, but more and more people gathered outside,

and they're trying to break down the door. they were convinced there was a burglar inside. Miraculously, the door was holding, but now, ten minutes had passed, and Charratt and I were panicking. If we'd been caught alone together, it would have been the end of us. So we texted our friends to see if they had ideas

to help us out of this situation, and at the end of a chaotic group chat, we came up with a plan. My boyfriend decided to take one for the team. Slowly, he opens the door, and he told the auntie that he'd have. had an upset stomach and had to use the toilet, but he was too embarrassed to come out as he had no water or paper to clean himself. So Auntie asked everyone to leave and went upstairs to get some

paper towels and water for him. And as soon as she left, I bolted out of there and ran all the way home. You know, we were both so scarred by this incident that we never saw each other again. You can listen to Conan Needs a Friend anywhere you find your podcast, and you can follow Conan O'Brien on Twitter at Conan O'Brien. Podcrushed is hosted by Penn Badgley, Navakavlin, and Sophie Ansari. Our executive producer is Nora Richie from Stitcher. Our lead producer, editor, and composer is David Ansari. Our secondary editor is Sharaff and Twistle.

This podcast is a ninth mode production. Be sure to subscribe to Podcrushed. You can find us on Stitcher, the Serious XM app, Spotify, Apple Podcasts, or wherever you listen. If you'd like to submit a middle school story, go to podcrush.com and give us every detail. And while you're online, be sure to follow us on social. It's at Podcrush, spelled how it sounds. And our personals are at Pembadjley, at Nava. That's Nava with three ends, and at Scribble by Sophie.

And we're out. See you next week. I've had that happen many times where the talent has been like, of course, no problem. And then someone else comes in and goes, that's not happening. Oh. It will not be done. I'm like trying to make eye contact. with your team

and see if they're going to like kill your TikTok. My team is completely and I say this knowing they can hear me they're very lame and they have no power. There's nothing they can do. Stitcher.