[Rerun] Conan O'Brien

Summary

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Podcrushed: [Rerun] Conan O’Brien

Hosts: Penn Badgley, Nava Kavelin, Sophie Ansari
Guest: Conan O’Brien
Release Date: June 24, 2026

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Episode Overview

This rerun episode of Podcrushed features beloved comedian, writer, and talk show host Conan O’Brien in a delightfully candid conversation with hosts Penn Badgley, Nava Kavelin, and Sophie Ansari. Staying true to the show’s format, the hosts and Conan explore the messy magic of middle school: awkwardness, vulnerability, and the formation of identity, laced with signature Podcrushed warmth and Conan’s quick wit. The discussion blends hilarious anecdotes, earnest reflections, and even a bit of “Gossip Girl” fandom, offering comfort and laughter about growing pains and self-acceptance.

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Key Discussion Points & Insights

1. Conan O’Brien: 100% Irish and 100% Awkward

Timestamps: 05:32–10:21

• Conan recounts discovering he is “100% Irish,” only for a geneticist to tell him, “That means you’re inbred… You people are just a bunch of Irish hillbillies that probably lived on the same farm.” (Conan, 06:13)
• Discusses the impact of physical awkwardness and feeling out of place during middle school: notably, his "long legs/short torso" dilemma and constant teasing about his “flood pants.”
• “I felt allergic to a lot of my reality.” (Conan, 08:14)
• Reflects on eventually embracing his unique traits as assets, but points out that it took years: “That’s the stuff later on that works for you.”
• Penn and Conan emphasize that even seemingly confident actors face awkward and tough years, challenging the illusion of perpetual coolness and composure.

2. The Pressure of Perfection and Social Media

Timestamps: 12:12–16:32

• The group discusses how social media amplifies comparison—against others and our own curated selves.
• Nava: “When you look back on your life, you’re comparing your current state to a state that doesn’t actually totally exist in reality.” (Nava, 15:13)
• Conan shares his unease with algorithmic memory videos on phones: “I’m just gonna look down at my phone and all of a sudden I hear this incredible song… I see, oh my God, I’m in Bermuda… I’m not ready.” (Conan, 15:48)

3. Family, Siblings, and Healthy Humbling

Timestamps: 16:42–20:44

• An archival audio clip of young Conan “interviewing” his athletic sister brings nostalgia and laughter.
• Conan describes growing up as one of six kids in a loving, sarcastic, and humor-driven Irish Catholic home: “Everything was done with sarcasm and humor… That was the way to communicate with people.” (Conan, 19:28)
• His family and now his children “keep him humble” by reminding him not to take himself too seriously—a “kind gravity… like a weighted blanket from spinning out of control.” (Conan, 18:39)

4. First Crush & Navigating Adolescence

Timestamps: 20:44–24:59

• Conan recounts a memorable middle school crush, recalling the visceral anxiety and sense of being an outsider.
• On seeing his crush years later: “Immediately, like, my voice cracked. She’s like, ‘Oh, Conan, your voice hasn’t changed!’” (Conan, 21:23)
• Discusses how kids mature at highly different rates, from “kids who bring in stuffed animals” to “kids who were dealing weed.”
• Emphasizes wanting his own children to grow up “as slowly as possible” to savor innocence and joy.

5. Embarrassing Middle School Story: The 25-Minute Intermission

Timestamps: 28:47–34:24 (Highlight 29:31–33:54)

• Conan narrates his infamous middle school “musical” performed with his best friend Jake, featuring:
  • A purposefully timed, Broadway-style 25-minute intermission in an 18-minute play—confusing and infuriating the entire school.
  • “We had no scenery, we had no costumes… but I was such a—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 after 25 minutes, curtain goes up. People were pissed.” (Conan, 32:03)
• Looking back, he laughs at his “incredible idiocy” and how performing was always his passion—even if misunderstood.

6. From Awkward Kid to Comedy Legend: Growth & Serendipity

Timestamps: 34:24–44:55

• Conan grew up “a thousand miles and a thousand years away from show business” but funneled anxiety into academic effort, leading him unexpectedly to Harvard and its comedy publication, The Lampoon.
• “By trying to give up this dream and work really hard… I ended up a week after showing up there… someone said, you should go check out the Lampoon. Bang, that changed my life.” (Conan, 35:52)
• Emphasizes that even in career lows, he never regretted not choosing a “standard path”—he “would have been a terrible lawyer.”
• Advice for young listeners: “You’re not penalized for failing as much as you think you will be… For the most part, I try to encourage people: try things. The good tends to stick in people’s thoughts and minds.” (Conan, 43:41–44:14)

7. Awkwardness, Confidence, and Evolution

Timestamps: 44:55–51:36

• Hosts and Conan dissect how mistakes in middle school feel catastrophic but fade, and the importance of not forgetting our awkward phases.
• “Middle school kids… The biggest mistake is they don’t realize other people are feeling the same stuff.” (Conan, 46:18)
• On confidence: “It took me so long to build up my confidence. It just took forever.” (Conan, 47:56)
• The panel underscores that growth and self-acceptance take time—even into your 40s and 50s. “I’m 59, so I still think I was forming in my 40s and into my 50s. Like, it just takes a long time.” (Conan, 50:20)

8. Gossip Girl Fanboy and Meta Moments

Timestamps: 53:50–57:47

• Conan reveals his family’s communal binge of “Gossip Girl”—amused by its melodrama and “parents [looking] six years older than the children.”
• Describes the surreal moment of requesting a selfie with Penn for his family group chat.
• Discusses the infamous series finale twist—Penn (Dan Humphrey) as Gossip Girl: “It’s not something I saw coming. But no one did. Also, if you go back and look at all the episodes and try and see how someone would have—it is not at all possible!” (Conan, 56:15–56:43)
• The trio riff on the show’s love of season-themed narration and pitch tongue-in-cheek alternate voiceovers.

9. Advice to Middle School Self and Listeners

Timestamps: 59:55–62:28

• Penn asks: If you could go back to your 12-year-old self, what would you say?
• Conan responds with humor and heart:
  • “More sunblock would be the first thing I would say.” (Conan, 60:01)
  • “You’re freaked out right now, you’re anxious. Trust me, things get better. It’s going to be okay.” (Conan, 60:32)
  • Acknowledges even with encouragement, young Conan would probably bicker with his older self.
• Final message: “Everything you’re feeling is exactly what you’re supposed to be feeling right now… it will get so much better.” (Conan, 61:51)

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Notable Quotes

• On being unique:
  “I felt allergic to a lot of my reality. And then it’s so interesting… that’s the stuff later on that works for you.” (Conan, 08:14)

• On social media pressures:
  “Everything’s curated. Someone’s posting just got dumped, or I’m here at a bad restaurant and they won’t wait on me, or—everything is a peak experience.” (Conan, 13:36)

• On family and humility:
  “My kids… are 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… 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…” (Conan, 18:39)

• On mistakes and risk-taking:
  “I try to encourage people: try things. The good tends to stick in people’s thoughts and minds. So why not try a bunch of things and don’t sweat.” (Conan, 43:41–44:14)

• On enduring awkwardness:
  “Kids… the biggest mistake is they don’t realize that other people are feeling the same stuff that they’re feeling.” (Conan, 46:18)

• On growing up:
  “You’re only, like, half cooked at that point… if you took a muffin out of the oven after six minutes, it wouldn’t be batter anymore, but it’s not a muffin.” (Conan, 49:22)

• To middle schoolers:
  “It does get better. And everything you’re feeling is exactly what you’re supposed to be feeling right now… Onward, it will get so much better.” (Conan, 61:51)

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Memorable Moments

• Conan’s “25-Minute Intermission” Story (32:03): His unwavering stage commitment to a Broadway-style intermission bewilders his entire school.
• Hosts and Conan “Rewrite” Gossip Girl Narration (58:17): Conan delivers on-brand quips, poking fun at melodramatic shows and ageless TV parents.
• Conan’s meta-reflection on therapy and talking to his younger self, bringing both honesty and self-parody (61:04).

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Listener Story Highlight

Timestamps: 63:01–64:44

• A listener from Tamil Nadu, India, shares a mortifying tale of being nearly caught making out with her boyfriend in an unused toilet room, leading to frantic improvisation and the abrupt end of their budding romance.

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Timestamps for Key Segments

| Segment | Timestamp | |--------------------------------------------|---------------| | Conan’s Introduction & Backstory | 05:32–10:21 | | Social Media & Memory | 13:36–16:32 | | Sibling Dynamic & Audio Flashback | 16:42–19:17 | | Middle School Crush/Rates of Maturity | 20:44–24:59 | | Embarrassing Middle School Play Story | 28:47–34:24 | | Path to Comedy & Harvard Lampoon | 34:24–35:59 | | Growth and Risk-Taking Advice | 43:41–44:55 | | Gossip Girl Fandom | 53:50–57:47 | | Conan’s Advice to Tween Self | 59:55–62:28 | | Listener Story | 63:01–64:44 |

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Tone & Style

Throughout, the tone blends playful banter, deep empathy, and Conan’s unmistakable wit. The hosts create a safe, open space for sharing both laughter and vulnerability. Conan seamlessly matches Podcrushed’s heart, sharing his own insecurities without pretense and offering assurance to listeners facing awkward and uncertain years.

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Bottom Line

This episode is a relatable, hilarious, and unexpectedly affirming look at adolescence—with Conan O’Brien proving that even legends outgrow their awkward phases, sometimes more than once. Whether you’re a parent, a current middle schooler, or just someone with adolescent scars, this is a must-listen for comfort and comic relief.

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Transcript

[Conan O'Brien]

Lemonade. 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.

[Nava Kavlin]

Oh, my God.

[Penn Badgley]

So good. That's great.

[Conan O'Brien]

Well, you're right. It's Groundhog Day in New York City. The groundhog saw his shadow, but there's no shadow of a doubt that love is coming to Madison in 13th Street.

[Nava Kavlin]

This is PodCrushed, the podcast that takes

[Penn Badgley]

the sting out of rejection one crushing middle school story at a time, and

[Nava Kavlin]

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.

[Penn Badgley]

And I'm Penn, a middle school dropout. Ok, so let's get into what everyone wants to hear about. How do we make a TikTok? I just want to stop. I just want to shut down as I say that. 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 a little insane.

[Nava Kavlin]

It's bold. It's really bold. Arrogant.

[Penn Badgley]

It's arrogant, maybe that we asked, but it's not because he's such a lovely guy. I'm just gonna 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,

[Nava Kavlin]

and I. I want to say I was the one who asked him. I took.

[Penn Badgley]

Definitely. I would never been able to.

[Nava Kavlin]

And I. Sophie, 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, like, even kind of acknowledged it in his response.

[Penn Badgley]

I would say that characterizes him in a lot of ways.

[Nava Kavlin]

He.

[Penn Badgley]

I mean, when I was on his show a few weeks ago, which isn't coming out for a little bit, but. Cause I'm real low on the, on the, on the order of priority. They've got everybody.

[Nava Kavlin]

The holiday episode.

[Conan O'Brien]

Yeah.

[Penn Badgley]

No, no, no, no, no. I'm not. I'm not a holiday episode. I'm a January episode. Which means, you know, you're just like, yeah, just put them. Just put them up on the shelf. No, no, Conan, I would say I don't know, just a lovely, encouraging person to be such a pillar of the world of public conversations and media.

[Nava Kavlin]

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, Pen and Nava, you had met him before, you had spent a little bit of time with him and so.

[Penn Badgley]

And we excluded you.

[Nava Kavlin]

Yep. I know it's becoming 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, like, 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. 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, but, but, but, but in person, it's funny.

[Penn Badgley]

Not funny at all.

[Nava Kavlin]

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.

[Penn Badgley]

Hey, guys, I have an idea. Why don't we just stop talking about him and start talking to him?

[Nava Kavlin]

Love it. Conan.

[Penn Badgley]

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 SiriusXM, a company we have no affiliation with. Ladies and gentlemen, please give it up for. Actually, we're gonna have to be right back. Stick around.

[Conan O'Brien]

Your call has been forwarded to voicemail. Hi, this is Zoe Deutch and Nick Robinson.

[Penn Badgley]

Our brand new movie. Voicemails for Isabel is all about those little moments that feel like the universe

[Nava Kavlin]

is looking out, feeling homesick.

[Conan O'Brien]

Then your sister calls, hearing that perfect song exactly when you need it. Please stay.

[Penn Badgley]

Sometimes life rigs things in our favor, like learning about your new favorite rom com. Voicemails for Isabel, now playing only on Netflix.

[Conan O'Brien]

Morning decisions. How about a creamy mocha Frappuccino drink? Or a sweet vanilla smooth caramel, maybe? Or white chocolate mocha?

[Nava Kavlin]

Whichever you choose, delicious coffee awaits.

[Conan O'Brien]

Find Starbucks Frappuccino drinks wherever you buy your groceries.

[Penn Badgley]

Thank you for coming.

[Conan O'Brien]

Thank you for having me.

[Nava Kavlin]

I saw a bit that you did on Colbert. It was sort of like a twofer. You talked about finding out that you were 100% Irish.

[Conan O'Brien]

Yeah. It's a true story. Yeah.

[Nava Kavlin]

Yeah. That's kind of rare, right?

[Conan O'Brien]

Yes.

[Nava Kavlin]

No.

[Conan O'Brien]

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. When I found out that I was 100% Irish, I said to the guy who gave me the result, I went, so that's good, right? And he said, tastes fantastic. Yeah. Like, I got 100%, as I know from my college days, 100% is pretty good. And he looked at me and he was like, no. I said, what does it mean? He said, it means you're inbred. It means you people are just a bunch of Irish hillbillies that probably lived on the same farm. But, yeah, it's hard to do. And I come from a long line of people who just married other 100% Irish people and have been doing 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.

[Nava Kavlin]

Cousin, just again and again.

[Conan O'Brien]

Hey, I just met you in the bathroom. You must live in my house. Let's get married.

[Nava Kavlin]

Is it convenient? Yeah. But in the bit you talk about, you describe yourself as having a short torso.

[Conan O'Brien]

I don't. So describe that.

[Nava Kavlin]

A short torso. Shame. Conan, please, right now.

[Conan O'Brien]

You seemed horrified when I walked in. You did seem.

[Nava Kavlin]

I was like, oh, my God. He was.

[Conan O'Brien]

No, I have, I have. I was very self conscious. Okay.

[Nava Kavlin]

This is what I was getting to. Yeah. What was it like in middle school?

[Conan O'Brien]

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? I 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 till 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 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 were 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 are people who have an awkward middle age experience, you know, middle school experience. I've had an awkward middle school experience. But there are 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, that puts them on a pedestal, everyone's led to believe that that is what they've always been. And they don't realize that a some of these people are miserable right now. I mean, a lot of them are or they're okay now, but they had a terrible awkward phase when no one was photographing them, you know, so.

[Penn Badgley]

Well, that is the spirit of the show in a way. I mean, I remember this period of life as the hardest.

[Conan O'Brien]

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.

[Penn Badgley]

Which is funny though, because I think you're right in a lot of ways. But I was still cast to play the awkward moment, which is so many

[Conan O'Brien]

levels of yes, but also awkward guy,

[Penn Badgley]

meaning on a TV show.

[Conan O'Brien]

Yeah, Awkward guy on a TV show that everybody was in love with any. 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 my family was moving around and I didn't feel like I belonged any whatever. They wouldn't know what you were talking about. They'd say, what are you talking about?

[Penn Badgley]

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, you go through waves with it, but still, yes. I present 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 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.

[Conan O'Brien]

Oh, my God.

[Nava Kavlin]

Yeah.

[Penn Badgley]

Every time you go to a party, you're just like, yeah, I just gotta throw on this tux.

[Conan O'Brien]

Yeah, yeah.

[Penn Badgley]

You know, 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.

[Nava Kavlin]

And I think even that's the case with people who aren't celebrities. Like, I remember feeling that way.

[Conan O'Brien]

What are we going to talk about people who aren't celebrities now?

[Penn Badgley]

No, that's not. We are podcast for.

[Conan O'Brien]

No, no. My business hours up. Excuse me.

[Nava Kavlin]

It's not in the right.

[Conan O'Brien]

We're 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.

[Penn Badgley]

What are we Talk

[Conan O'Brien]

anyway. Go ahead.

[Nava Kavlin]

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. I was like, what happened? Why did we fall out? Big mistake. Never write your remedies from years ago and ask 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.

[Conan O'Brien]

I think that's the thing that's exacerbated now by social media, 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. Someone's posting just got dumped, or I'm here in a bad restaurant and they won't wait on me, or. Everything is a peak.

[Penn Badgley]

That's what TikTok is for.

[Conan O'Brien]

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 sense, this fomo, this sense that everyone else is living this amazing experience, which isn't true.

[Nava Kavlin]

I still feel.

[Penn Badgley]

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 just now it's like that.

[Nava Kavlin]

You usually feel like you're better than everyone else. Right?

[Conan O'Brien]

Generally speaking, that again, Pen and I are on the same page. We both think we're the best versions of a human being.

[Nava Kavlin]

There's also this other weird thing.

[Penn Badgley]

I'm a hundred percent.

[Conan O'Brien]

I'm 100%.

[Nava Kavlin]

So you are, in a way.

[Conan O'Brien]

Exactly.

[Nava Kavlin]

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, like, 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.

[Conan O'Brien]

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.

[Penn Badgley]

Yeah.

[Conan O'Brien]

Memories, memories and memories.

[Penn Badgley]

It's amazing, actually.

[Conan O'Brien]

It is absolutely amazing. But. But I'm not ready for it ever. I'm just like, you know, I just got out of the house and I'm gonna. Okay. And I'm just gonna look down at 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 you. Oh, my God, my wife is beautiful. Oh, my God, my children are so young. We're carving pumpkins and I'm not ready. And it's this huge emotional rush and I think there's no lead in to it.

[Nava Kavlin]

So interesting.

[Conan O'Brien]

There's never. And I just always put the phone down and go like, that was. I guess it's over now. But it was a great life.

[Nava Kavlin]

Exactly. Conan. Speaking of things you're not prepared for, 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.

[Conan O'Brien]

Hi, I'm Conan o', Brien, and here we are with Kate o', Brien, the softball star.

[Nava Kavlin]

Hey, Kate, how you doing?

[Conan O'Brien]

Pretty good, pretty good.

[Nava Kavlin]

Hey, Kate, I understand you're on the

[Conan O'Brien]

softball team your freshman year in high school. Yeah, I was.

[Nava Kavlin]

I was out there in the outfield,

[Conan O'Brien]

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 gonna 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.

[Penn Badgley]

Fully. You'd actually discover time, Even the tape quality sounds.

[Conan O'Brien]

Yeah.

[Penn Badgley]

I mean, it's.

[Conan O'Brien]

I know, I know it's ridiculous 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.

[Nava Kavlin]

You sound like. But I love the little laugh at the end. That was my favorite. The little ha ha at the very end.

[Conan O'Brien]

Woody Wood. Patrick. Yeah, they have. Mostly for me, yourself. That's me putting a laugh in. In case there is no laugh.

[Nava Kavlin]

Yeah.

[Penn Badgley]

Yeah.

[Conan O'Brien]

That's your laugh track. You know what I should do? I should have done that throughout my career whenever I made a joke anyway. But if you ask me, that's more like Bill Clinton. Nah. Just in case there was no laugh, so.

[Nava Kavlin]

So you were interviewing your younger sister?

[Conan O'Brien]

Yeah, yeah. I have two younger sisters. That's Kate. I have another younger sister, Jane. But that's just me doing a standup 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.

[Nava Kavlin]

I love the banter between you two.

[Conan O'Brien]

It was really sweet. Yeah. You know what's nice is 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. Really? In a good way. No, that's healthy. It's like.

[Nava Kavlin]

Healthy. Yeah.

[Conan O'Brien]

Well, I think it verges 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.

[Nava Kavlin]

My siblings are like that, too. They definitely keep me humble. But you were one of six.

[Conan O'Brien]

Yeah.

[Nava Kavlin]

What was that like growing up? One of six? Did you do a lot of stuff like that with your siblings?

[Conan O'Brien]

Yeah, she plays. 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. 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.

[Nava Kavlin]

I was like. And it's not now.

[Conan O'Brien]

You feel that today, but if taken to an extreme, you can monetize it, which is true of men, which is true of sex for a 12 year old. Yeah. 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.

[Nava Kavlin]

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.

[Penn Badgley]

Yeah.

[Nava Kavlin]

What were you like and could you tell us about your first love and heartbreak?

[Conan O'Brien]

Well, there was this girl that I, in fifth grade that I had a huge crush on and her first name was Lara. 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? Like running water. 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 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 at an outdoor cafe and she said, oh, hey, Conan. And I was like, oh, hi. Immediately, like, my voice cracked. She's like, oh, Conan, your voice hasn't changed. But you're, 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 till later and, you know, I was not. There were kids. I remember 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 you were like, what? How is that, how am I even the same species as that? Yeah, he's my. And check you're my. How old are you again? I'm 12.

[Nava Kavlin]

Ken's like, Me too.

[Conan O'Brien]

Yeah, I'm 12 too. I just shaved 10 minutes ago. But you got a Full beard. I know.

[Nava Kavlin]

Yeah, that's.

[Conan O'Brien]

I gotta go drive a truck now. Drive a truck. You're 12.

[Nava Kavlin]

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.

[Conan O'Brien]

Really?

[Nava Kavlin]

Was that you, Sophie? Were you the weed dealer?

[Conan O'Brien]

Yeah. No, but I think that.

[Nava Kavlin]

No, just for. For legal purposes.

[Conan O'Brien]

The disparities then are mind numbing. And then there are kids that 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. I want them to be excited about Christmas for as long as 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.

[Nava Kavlin]

Yeah, right.

[Penn Badgley]

How old are they now?

[Conan O'Brien]

They are. My daughter's 19, and my son turns 17 today.

[Nava Kavlin]

Wow. What's his name?

[Conan O'Brien]

His name's Beckett.

[Nava Kavlin]

He's not gonna hear it today, but happy birthday, Beckett.

[Conan O'Brien]

Yeah. And. And he very much. I've never missed a birthday of his, 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, no. I said the most important thing I told him as 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 your podcast, and the purpose of your podcast is to help children my son's age.

[Penn Badgley]

Only on the surface, Conan. Only for the numbers.

[Nava Kavlin]

It all comes down to the bottom line.

[Conan O'Brien]

I flew here at my own expense.

[Penn Badgley]

We all work for Sirius.

[Conan O'Brien]

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 have not crossed this route before.

[Nava Kavlin]

If you know anyone nice, Conan, please let me know. To be your child.

[Conan O'Brien]

Are you to adopt them? Yeah. Oh, you're okay. I thought you meant if you knew any nice people that want to be your child.

[Nava Kavlin]

Stick around. We'll be right back.

[Penn Badgley]

Summer in the city can be tricky when it comes to fashion. Just getting dressed in the morning so they don't have to change once or twice before the day is over. That's a challenge. I want to look good in what I'm wearing without thinking too much about it, you know, and in the heat, it's lighter fabrics, better materials, pieces that just feel good the moment you put them on. Done. That's what I want. And that is why I like what Quince is doing. They focus on high quality essentials like breathable linen, soft organic cotton, washable silks. Ooh. But without the luxury markup. Quince has classy, sharp everyday pieces like 100% European linen pants and tops with styles starting at $32. Unlike most good looking denim, there's a soft, easy to wear, Right? And there's sweaters. Again, it's organic cotton. They're perfect for layering on cool summer nights. And everything at quince is priced 50 to 80% less than similar brands. So how do they do that? Well, Quince works directly with ethical factories and cuts out the middlemen. So you're paying for quality, not for brand markup. And actually, they don't just have clothing. Quince has really become a destination for elevated essentials across home, kitchen, bedding and beyond. They make it really easy to bring a more premium feel into your everyday life at home and what you're wearing out. I'm rocking the 100% European linen drawstring beach pants in like a nice sort of light forest gre. While I got my wife a pair of the wide leg version for women, a different color. If you're wondering if we're matching, we're not. I got her a cream, like a creamy gray heather sort of thing. I know we both appreciate a fine looking, breathable pants in the summer that looks elevated. But you know, we aren't afraid of the kids getting their sweet, sweet grubby little hands on. Right. Elevate your summer wardrobe. Go to quince.com podcrushed for free shipping on your order and 365 day returns. Now available in Canada too. That's Q-U-I-N c e.com podcrust for free shipping and 365 day returns. Quince.com podcrushed this episode is brought to

[Conan O'Brien]

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[Nava Kavlin]

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[Nava Kavlin]

A question that we love to ask anyone who comes on the show is to share an embarrassing story from middle school. Do you have any that you can share?

[Conan O'Brien]

Have any? That's the. That's like.

[Penn Badgley]

Can you narrow it down a lot?

[Conan O'Brien]

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, his friends. I'll shout him out. Jake Fleischer was my best friend. And we decided we were gonna write a play. And it was actually a musical. Now, we didn't write the music. We just took existing tunes and wrote different things.

[Nava Kavlin]

So you wrote the pilot of Glee?

[Conan O'Brien]

Exactly. Yes, we did. And I'm still suing the Glee people because I think they ripped me off. But so we did this. We wrote this play. It was so ridiculous. Cause 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. Dun, dun, dun, dun, dun, dun, dun. We're gonna do the, 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 gonna 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.

[Nava Kavlin]

Like a special performance. It wasn't a show or anything.

[Conan O'Brien]

And it was like, you know, hey, some kids wrote a play and it's.

[Penn Badgley]

And it was just the two of you.

[Conan O'Brien]

And it was the two. Just the two of us.

[Nava Kavlin]

Okay, Jake and Conan.

[Conan O'Brien]

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 gonna give it our best shot. Dun bump. 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 was 25 minutes. And so I remembered very clearly talking this down the day of the show. And I said, all 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.

[Nava Kavlin]

Jake had some sense.

[Conan O'Brien]

We had no scenery, we had no costumes, really. There was no changeover. Nothing had to happen. But I was such a. 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, and they're like, hey, all right, Whoa. We're backstage 5 minutes, 10 minutes, and you can hear, like, people are thinking, what is going on? And then 25 minutes, curtain goes up. And people were pissed.

[Nava Kavlin]

I'm amazed they stayed.

[Conan O'Brien]

You're pissed. Yeah, they had to stay. And so after, 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.

[Nava Kavlin]

It's show business.

[Conan O'Brien]

Yeah, yeah. And Then I remember teachers coming over and going, can I. Could we talk to you for a second? What were you doing for 25min?

[Nava Kavlin]

Nobody came up in a second AD.

[Conan O'Brien]

I think they like, no one knew. And there was very much like, well, we assume that they're building this incredible set, they're doing something, then comes back up again. And we've done nothing different. Nothing's done. It's like if we stop this podcast right now. And I said, it's time for the intermission. 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.

[Penn Badgley]

Did you have to like force Jake back?

[Conan O'Brien]

Yes, from.

[Penn Badgley]

He was like, Conan, we gotta pull the corner man.

[Conan O'Brien]

Exactly. No, Jake to his credit, and 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 wanna be in Broadway or not? What are we. Yeah, I was so. I was an incredible idiot who came out victorious.

[Nava Kavlin]

I was gonna ask you, did that continue for the rest of your childhood, your interest in performing?

[Conan O'Brien]

Yeah, I was always interested in it, but I did think, yeah, 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. So I wasn't around people in show business. My parents are professionals. My dad's a research scientist, my mom's a lawyer. They're serious people. And so I was very interested in it. And then said, well, anyway, I want to make something of myself, so 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 hero 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.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

Then I was all comedy all the time. So my best efforts to not pursue this led me right back to it.

[Nava Kavlin]

I love that.

[Penn Badgley]

So when was your. Sorry, go ahead.

[Nava Kavlin]

No, I was like, in your lowest moments in your career, did you ever regret it? Were you like, I wish I had done this, like, other standard path, or have you always.

[Conan O'Brien]

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 1988, and I was a young lad, and this writer's strike, I get hired at snl. It's the dream job. So excited. I do a couple of shows, and this writer's strike hits. And so suddenly, Bob Odenkirk, who is a writer that I shared an office with, and Robert Smigel, they said to me, hey, Conan, we're gonna go to Chicago and just do, like, a silly show of sketches that would never make it on snl. You seem like the kind of guy that would wanna come with us. Do you wanna do it? And I said, yes, I do.

[Nava Kavlin]

Right up your alley.

[Conan O'Brien]

So I remember doing this show at the Victory Gardens Theater in Chicago in 1988 called Happy, Happy. Good Show. And, you know, 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.

[Penn Badgley]

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.

[Nava Kavlin]

I think

[Conan O'Brien]

I was very interested in show business. And I was one of six kids, and 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 charts. No one's tap dance. Tap dancing in Les Conan. 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 Berklee School of Music in Boston named Stanley Brown, who had learned from Bill Bojangles Robinson.

[Nava Kavlin]

Wow.

[Conan O'Brien]

He was this old, like I want to say 70 year old black man who. And, and all of the people there, everybody was black except me. There was this one orange haired boy who looked like the Wendy's, 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

[Nava Kavlin]

like, ugh, this guy.

[Conan O'Brien]

And like these incredibly sexy women who were doing modern tap and jazz tap. And I'm like, hi, everybody. Do you, anyone have a cane and a straw hat? You know, one, two by four, shuffle after buffalo. And so I, but so I was pursuing 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

[Nava Kavlin]

you could pull out of your back pocket now? Like if someone.

[Conan O'Brien]

Not really. I know, I know a step or two, but not really. And no, it was, you know, I

[Penn Badgley]

took tap for a moment.

[Nava Kavlin]

I was about to say I feel like there should be a tap off.

[Conan O'Brien]

Exactly.

[Penn Badgley]

Yeah.

[Conan O'Brien]

And nothing, there's nothing better for podcast cast than a dance off. You just can hear people going like

[Penn Badgley]

tapping right now.

[Conan O'Brien]

And you two going like, this is incredible.

[Nava Kavlin]

Right now. Imagine Conan Ryan are tapped facing in this studio. But you can't.

[Conan O'Brien]

The pen just took it up a notch. No, no, no. Conan's in the lead now.

[Nava Kavlin]

Pen, this is sounding like F1.

[Conan O'Brien]

Yeah. Backflip, front flip.

[Penn Badgley]

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.

[Conan O'Brien]

I wouldn't allow you on. Remember we had a. And 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 allowed. We had a picture in Rockf Center. Ben Bad said, this man is not to be allowed on the late night program. Yeah. And it's because he passed a bad check. 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.

[Penn Badgley]

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

[Conan O'Brien]

about for reasons of criminal trespass, which

[Penn Badgley]

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 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 I just loved being able to be on your podcast and to speak for cause I just love speaking at length, as we can see.

[Conan O'Brien]

So it was great.

[Nava Kavlin]

Is this going Snowpad?

[Conan O'Brien]

No, no. He did a six hour podcast. I didn't get a word in edgewise.

[Nava Kavlin]

I believe it.

[Penn Badgley]

How do you feel about your ability to evolve this format and to.

[Conan O'Brien]

Well, first of all, I feel very fortunate that there people working for 15, 20 years on podcasts, 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. You know, 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.

[Penn Badgley]

I like that.

[Conan O'Brien]

Which is nice. I think you're remembered for. Most often you're remembered. 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, did 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.

[Nava Kavlin]

It's so encouraging, Conan.

[Conan O'Brien]

It is, yeah.

[Penn Badgley]

Do you think that's true in middle school, however? Cause it does seem to be a bit inverse.

[Conan O'Brien]

Well, the thing in middle school, I think is people feel like everything, any matter, mistake matters.

[Nava Kavlin]

Yeah, you're hyper aware.

[Conan O'Brien]

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 remembered feeling that way all the time when I was young. Like, I am done. And I remembered, you know, I'd be like, there are 15 year olds. Are 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, 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. And I thought, oh my God, to think that that was your peak.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

And I think somewhere, I swear to God, this kid, this guy now who's my age is wandering around telling people, fourth grade should have seen me.

[Nava Kavlin]

Fourth grade is a good year.

[Conan O'Brien]

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 a 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 all of this wisdom does come with age. Like, 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 long enough, which kids don't have that perspective.

[Nava Kavlin]

It's totally true. So our podcast is called Pod Crushed with the ed. And the reason sort of initially was our idea was marketing was just take the sting out of rejection.

[Conan O'Brien]

It looked good on a T shirt.

[Nava Kavlin]

Yeah, it just looked better than podcrust. 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, 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 harder that we have things.

[Conan O'Brien]

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. It was just took forever.

[Penn Badgley]

It just felt like it took forever in middle school. I don't care who you are in. 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.

[Conan O'Brien]

I'm still not comfortable with that word.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

Yeah.

[Nava Kavlin]

I have never called it love.

[Conan O'Brien]

I'm 77 years old and I'm comfortable with the concept of telling someone I love them or I need love from them.

[Nava Kavlin]

I was like, wow, you look really good for 77.

[Conan O'Brien]

When Penn first met me, he was just stunned by the amount of work I've had done and how bad it is.

[Nava Kavlin]

You can tell right away.

[Conan O'Brien]

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.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

So, yeah. Well, you know, first of all, I'll tell you the. The title of my podcast is Conan o' Brien Needs a Friend.

[Penn Badgley]

That's right.

[Conan O'Brien]

Which is a joke, but also not a joke.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

But also a joke. So it's one of those things that just kind of flips around. But, you know, it's interesting because I. You know, 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.

[Penn Badgley]

As a.

[Conan O'Brien]

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.

[Penn Badgley]

How long does a muffin cook for?

[Conan O'Brien]

Well, it depends.

[Penn Badgley]

Your altitude.

[Nava Kavlin]

Yeah, that's not the point.

[Penn Badgley]

Sorry.

[Conan O'Brien]

I do a lot of my. No, I do a lot of my. 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, no, no, no. You've got. There's.

[Penn Badgley]

You're so long.

[Conan O'Brien]

It takes so long. Long.

[Penn Badgley]

Like now I just turned 36, and I feel like I'm honestly just starting to really lighten up. You know, I've heard 40 is even better.

[Conan O'Brien]

Well, I got some bad news for you. No, no, but see, the thing is, you're all very young, and you are gonna still keep evolving. That's what people don't realize, is that there's this evolution that happens that continues. So. 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.

[Nava Kavlin]

That's very hopeful. The other day, I had this realization, actually. I was watching this as I was watching the finale, and I don't. You know, it gets a little bit.

[Penn Badgley]

Just weeping uncontrollably.

[Nava Kavlin]

But I realized, like, I'm 28, and I can sometimes feel like I am put out to pasture, like it's over.

[Penn Badgley]

Are you a millennial?

[Nava Kavlin]

For me, I'm on the cusp. I'm like, I'm 94, and I think 96 is a gen. 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.

[Conan O'Brien]

It's not completely hopeful. Because what happens soon is I'll Start devolving. That's the problem. I'm gonna start losing.

[Penn Badgley]

So where's that peak moment?

[Conan O'Brien]

I am two years. I think right now. I'm two years into devolving. 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 spec.

[Penn Badgley]

All right, can we go?

[Conan O'Brien]

Your bodies are going to fall apart.

[Nava Kavlin]

And we'll be right back.

[Conan O'Brien]

Introducing Taco Bell's new Jalapeno Citrus Salsa. With bright citrus, real red jalapenos, guajillo chiles. Usually, you add sauce to the food, but when the sauce is this good, the food is just there to get the sauce to your mouth. That rolled queso. Not a rolled quesadilla anymore. Now it's a sauce shovel. Taco Bell's Jalapeno Citrus Salsa. Get it with any item on the Cantina Chicken menu while it's here. The participating US Taco Bell locations, for a limited time only while supplies last. Contact store for availability. Hi, diva. It's Rachel and Jordan. Yeah, hi.

[Penn Badgley]

Quick question.

[Conan O'Brien]

Why are you not spending your Venmo balance? Yeah, we're concerned you can, like, buy stuff with it. You love buying stuff and earn cash

[Nava Kavlin]

back on eligible purchases.

[Penn Badgley]

You love purchasing eligible things.

[Conan O'Brien]

So the money your friend sent you yesterday, that's today's Rom or rideshare or eye patches.

[Penn Badgley]

The skincare kind, not the pyro kind.

[Conan O'Brien]

Spend with Venmo and you can earn cash back with Venmo stash. Venmo stash bundle terms and Exclusions apply. Makes $100 cash back per month. See terms at Venmo Me Terms, Idaho.

[Nava Kavlin]

Verification required to use a Venmo balance.

[Conan O'Brien]

Do you hear that? Sounds like breakfast is ready. Because Quaker's coming in hot with morning nutrition. 100% whole grain oats and a good source of fiber to fuel the rhythm of your morning and kickstart your day. And that sounds absolutely delicious. Fuel to start. Whatever's next. Quaker official sponsor of FIFA World Cup 26. Let's go.

[Nava Kavlin]

So I know because I was able to sit in on your interview with Pen, that you are a Gossip Girl. Stan and I wanted to know.

[Conan O'Brien]

Stan seems like a. I feel like

[Nava Kavlin]

Conan was a Stan, but.

[Conan O'Brien]

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 it, Bass Industries. I bought out your controlling share. I bought out your 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. And you're like, I can't do that now. You know, so we started watching it, and then. I never do this. I never do this. Cause I get to interview all these, you know, really cool, great people. I never ask. But when Penn did the show, I said, I hate to do this, but can I get a selfie with you?

[Penn Badgley]

No. And tell him what I said.

[Conan O'Brien]

What did you say?

[Penn Badgley]

No.

[Conan O'Brien]

He said, no. And he shut me down. Yeah. And he said, don't turn.

[Penn Badgley]

Of course.

[Conan O'Brien]

No. He said, no, no, no. So I said, I never did, 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. Aw. That's like. You know, and it's just funny because I, like, it was just this moment of. That's been something we've bonded over, so it's really fun.

[Penn Badgley]

I think as a family, you should start watching the one where I put people in cages.

[Nava Kavlin]

You know, once Beckett graduates.

[Conan O'Brien]

Yeah, yeah, yeah. Anything that encourages people to masturbate in a public space.

[Nava Kavlin]

But I did want to ask you. So as a. As a Gossip Girl fan, what did you think of the reveal that Penn Badgley slash Dan Humphrey was Gossip Girl?

[Conan O'Brien]

Well, thanks for the spoiler. It's the one thing I.

[Penn Badgley]

Did you know that.

[Conan O'Brien]

No, I did know that. I was like, oh, no, we ruined it. No, I did know that. The only thing it blew is it. It's not something I saw coming. But no one did.

[Nava Kavlin]

But the writers. The writers didn't.

[Conan O'Brien]

No, no. Trust me. Also, if you go back and look at all the episodes and try and see how someone would have. It is not at all possible. So I just thought, like, okay, I see what they. You know, they were in a corner, and they. And so why not?

[Penn Badgley]

They wrote their way out.

[Conan O'Brien]

They wrote their way out beautifully.

[Penn Badgley]

I mean, What? You know what? You isn't in that position at some point.

[Conan O'Brien]

Yeah, exactly. But I think it's cool that you go down actually now.

[Penn Badgley]

I agree. As a person who was somewhat transparently, publicly, maybe inappropriately, sometimes shared about the resistance and conflict I had of being on a show like that or just always kind of being in the public eye, I think it's interesting that I am the. I'm Gossip Girl.

[Conan O'Brien]

You're a Gossip Girl? Yeah.

[Penn Badgley]

I take that as a good.

[Conan O'Brien]

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.

[Penn Badgley]

Yeah.

[Conan O'Brien]

Because there are times where Gossip Girls, like, well, if you ask me. And like, no, no, no. You're not even. You weren't there. It's the episode where you're. You're trapped in a mine in Mexico and, you know, xoxo, like, no. What? You tweeted that from the mine. Now people are going to go looking for the episode where you're trapped in a mine.

[Penn Badgley]

Part of me wants to, just for the enjoyment of the real Stans 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.

[Conan O'Brien]

Yeah.

[Nava Kavlin]

Should we do it?

[Conan O'Brien]

Should we do that?

[Penn Badgley]

I mean, if they have $10 million,

[Conan O'Brien]

how much time he's gotta get paid?

[Penn Badgley]

Yeah. I mean,

[Conan O'Brien]

well, winter came early to New York, but the real chill's on the Upper east side. Oh, that's a good one. 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.

[Nava Kavlin]

Oh, my God.

[Conan O'Brien]

So good.

[Penn Badgley]

That's great.

[Conan O'Brien]

Well, let's rewrite. Rewrite. It's Groundhog Day in New York City. The groundhog saw his shadow but there's no shadow of a doubt that love is coming to Madison and 13th Street. That's too low. Too low. Too low. Too low.

[Nava Kavlin]

That's at the mine in Mexico.

[Conan O'Brien]

They also. My other favorite option, 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 gotta 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. I remember when I had you when I was six. It really makes me scandal at the time. 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 who? Who's the father here and who's the kid?

[Penn Badgley]

Yeah, we ask everybody. So you're not special.

[Conan O'Brien]

It's just getting intense.

[Nava Kavlin]

Yeah.

[Conan O'Brien]

If they could give us some money,

[Penn Badgley]

if you could go back to your 12 year old self.

[Nava Kavlin]

Yep.

[Penn Badgley]

What would you say? What would you do?

[Conan O'Brien]

More sunblock would be the first thing I would say. There's a thing called skin cancer and you were a ticking time block. 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 gonna be, it's all gonna be good. It's all gonna 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. I've been, you know, 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, missing the point. I'm coming to you from the future.

[Nava Kavlin]

What is that? Hairspray?

[Conan O'Brien]

Did you put hairspray 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 guy? Shut up. I'm not here long.

[Penn Badgley]

I don't have much time.

[Conan O'Brien]

I don't have much time. It's going to be okay. Yeah, so what? I don't think it's gonna 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. We would end up bickering and yelling at each other. So. 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. Dor Shut up, Conan. Yeah, what's wrong with Conan? I. 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.

[Nava Kavlin]

Thank you.

[Conan O'Brien]

Thank you so much. Well, thank you so much for having me. And this, this worked out really nicely. Cause 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.

[Nava Kavlin]

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. One stick around.

[Penn Badgley]

Oh, I think you got to keep that.

[Nava Kavlin]

It's pretty good for sure.

[Penn Badgley]

I'm from Tamil Nadu, 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 season. 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 one 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 10 minutes had passed and Charette 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 bunch of plan. My boyfriend decided to take one for the team. Slowly he opens the door and he told the auntie that he'd had an upset stomach and had to use the toilet. That 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.

[Nava Kavlin]

Home.

[Penn Badgley]

You know, we were both so scarred by this incident that we never saw each other again.

[Nava Kavlin]

You can listen to Conan Needs a Friend anywhere you find your podcasts and you can follow Conan O' Brien on Twitter @Conan O'. Brien.

[Penn Badgley]

Podcrushed is hosted by Penn Badgley, Nava Kavlin and Sophie Ansari. Our executive producer is Nora Richie from Stitcher. Our lead producer, editor and composer is David Ansari. Our secondary editor is Sharaf and and Twistle. This podcast is a ninth mode production.

[Nava Kavlin]

Be sure to subscribe to PodCrushed. You can find us on Stitcher, the SiriusXM 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 socials. It's odcrush, spelled how it sounds and our personals are Pembadgley Ava, that's Nava with three N's and Scribble by Sophie. And we're out. See you next week.

[Conan O'Brien]

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, they will not be doing that.

[Nava Kavlin]

I'm like trying to make eye contact with your team. They're gonna like kill.

[Conan O'Brien]

That's not. 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.

[Nava Kavlin]

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[Penn Badgley]

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[Conan O'Brien]

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[Penn Badgley]

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[Conan O'Brien]

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[Penn Badgley]

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[Conan O'Brien]

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[Penn Badgley]

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