Keep Paddling with Conan O’Brien

Summary

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Podcast Summary

Podcast: IMO with Michelle Obama and Craig Robinson

Episode: Keep Paddling with Conan O’Brien
Date: March 4, 2026
Hosts: Michelle Obama & Craig Robinson
Special Guest: Conan O’Brien

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Episode Overview

This lively anniversary episode of "IMO" features Michelle Obama and Craig Robinson in conversation with comedian and talk show icon Conan O’Brien. Together, they reflect on family influences, the journey of self-discovery across adulthood, lessons from career pivots, and the importance of perseverance (“keep paddling”)—all delivered in the show's signature mix of honesty, wit, and warmth. Notably, Conan opens up about his upbringing, the roots of his humor, and the value of resilience—themes that resonate through listener advice and funny anecdotes from the trio’s personal and professional lives.

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Key Discussion Points & Insights

1. Reflections on the IMO Podcast & Family Legacy

• Celebrating One Year
  Discussing the show's first anniversary, Michelle and Craig express gratitude to the staff, supporters, and listeners (02:01–02:48). They credit their late mother for instilling the values behind the podcast.
  • “This show is a tribute to her because of the parenting that mom and dad gave us ... a lot of the IMO's, the opinions we have, come from the wisdom they passed down to us.” — Michelle (04:25)

2. Introducing Conan O'Brien: Comic Origins & Family Influence

• Upbringing & Early Comedy
  • Conan recounts growing up in a big Irish Catholic family and comedic competition at Sunday dinners (10:32–13:51).
    • “Everything starts at the kitchen table. ... People would jockey for who's the funny one at the table and who can really make mom and dad laugh.” — Conan (11:38)
  • His parents’ achievements, especially his mother’s legal career under challenging gender norms, were pivotal (17:19–21:58).
    • “In those days...she’d go to a meeting...they would all go into the dining room, but she couldn't go in because it's men only.” — Conan (20:28)

3. The Pressure and Beauty of "Firstness" & High Standards

• The Weight of Being "First"
  Michelle draws parallels between Conan’s mother’s pathbreaking career and the scrutiny the Obamas faced in the White House (24:16–25:16).
  • “In order to get where we are, as you've seen and your mother, you don't get here without being damn near perfect. We don't get to fail 2, 3, 5, 7 times.” — Michelle (24:16)

4. Career Path, Luck, and Finding One's Calling

• Conan’s Unlikely Career Journey
  He details his nerdy adolescence, Harvard education, and journey into comedy via The Lampoon (26:26–33:02).
  • “Up until that point in my life, I thought anything good has to come through suffering. ... This was the first time in my life...that I would say, hey, here, what about this? And people would say, that's great. And I'd say, really? ... I had fun.” — Conan (32:27)
• Embracing Luck and Preparation
  The group discusses the interplay of preparation and luck in career success (45:08–46:24).
  • “It's that old saying, you make your luck. ... I get very angry when people don't give it up for luck.” — Conan (45:29)

5. Mentorship and Optimism for Younger Generations

• Conan emphasizes optimism and the importance of encouraging and supporting young people in comedy and life (47:02–52:58).
  • “When I see young people that are really funny, I choose not to be threatened. I choose to be excited.” — Conan (47:03)

6. Resilience, Setbacks, and the African Queen Metaphor

• Conan shares his “African Queen” metaphor about persistence through adversity (47:18–50:45).
  • “There've been probably 35 times in my life when I thought dead on the boat...And then it's just learning to roll with it, reset, recommit, and look for the next opportunity.” — Conan (48:53, 50:45)

7. Meeting His Wife and Family Life

• Conan recounts the accidental, unscripted on-camera moment when he met his wife, Liza (51:19–54:39), and their late mothers' enduring influence.
  • “We just met and then ... we just talked on the phone.” — Conan (53:42)

8. Crafting for the Oscars and the Reality of Showbiz

• He discusses prepping for the Oscars, the grind of testing material in clubs, and the unpredictability of entertainment (57:36–63:27).
  • “You know, you're in some back room or an alley standing around with other comics ... you're in an alley in a T shirt and jeans.” — Conan (59:56, 60:50)
• The group has a running joke about ventriloquism (61:07–61:48).

9. Comedy in Changing Times

• The panel discusses how divisive news cycles make comedy more challenging and the importance of seeking humor in everyday life (66:37–68:35).
  • “Things are so divisive right now. ... It's gotta be just a really tough task.” — Conan (67:36)

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Audience Question & Group Advice

[74:06] Listener Question from Jake in Indiana:

• Q: Jake feels lost in his career path after achieving his dream job early, shifting jobs, and now being unsure of next steps.

Key Advice & Insights ([74:50]–[83:28]):

• Conan:
  • Normalize uncertainty: “This is called being 26.”
  • It’s okay to “tread water”—progress isn’t constant.
  • “No one escapes it. ... This is a feeling you’re going to have now and then it’s going to go away and ... revisit you.”
• Michelle:
  • Most people don’t follow a straight path; it’s normal to switch passions and professions, even later in life.
  • Be patient, stay open, and keep evolving: “You want to keep evolving ... that work of figuring yourself out, it’s waiting for you.”
• Craig:
  • Try different things, experiment, and don’t worry about failure.
  • Quoting Neil deGrasse Tyson: Procrastinators often have highly engaged minds—sometimes your brain is working through problems without conscious effort.

Notable Quote:
“There are going to be many lives. ...And that's what you want out of life.” — Michelle (79:17)
“You have more room for error than you think you do.” — Conan (82:43)

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Memorable Quotes & Moments

• On Comedy & Parental Influence:
  “You’re probably for the rest of your life gonna be trying to live up to what your mom or your dad would want. And that stays with you.” — Conan (14:08)

• On Resilience:
  “It keeps happening. Over and over and over again. And then it's just learning to roll with it. To roll with it and say, okay, what's my next opportunity?” — Conan (48:53)

• On Luck:
  “I've been very, very lucky, and I give it up for that. I also know that I work really hard and I prepare ... but I get very angry when people don't give it up for luck.” — Conan (45:29)

• On Life’s Nonlinear Paths:
  “The 20s and the 30s and I would even say now the 40s are the period where you aren’t gonna know.” — Michelle (78:30)

• On Trying New Things, Even Later in Life:
  “I've gotten to a point in my life where I think, give it a shot.” — Conan (85:04)

• On Family Legacy:
  “We didn’t lose them. ...They imprinted on us and they're with us. So you're always gonna have your mom. I'm always gonna have my parents. Liza's always gonna have her mom.” — Conan (56:10)

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Timestamps for Key Segments

• Family, Podcast Anniversary, and Legacy: 02:01–05:48
• Conan Introduced & Upbringing: 07:25–13:51
• Comic Family Dynamics: 11:30–13:51
• Parental Pressures & Irish-Catholic Family: 20:28–25:16
• Harvard and the Harvard Lampoon: 26:26–33:02
• Making It in Comedy & Luck: 38:36–46:24
• Persistence/African Queen Metaphor: 47:02–50:45
• Meeting His Wife Liza: 51:19–54:39
• Advice Segment (Listener Jake): 74:06–83:28
• Pivot to Acting & New Challenges: 83:32–86:13

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Notable Lighter Moments

• Conan and Craig banter about their heights and athletic abilities (26:00–27:16).
• Ongoing ventriloquism jokes, culminating with a surprise ventriloquist dummy for Craig (61:07–89:52).
• The group debates horoscopes and “manifesting” with good-natured skepticism (72:12–73:38).

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Takeaways

Resilience, reinvention, and humor are essential to navigating careers, family, and life’s unpredictabilities. The wisdom of parents—and the voices of childhood—echo through our journeys, and success often lies in blending passion with preparedness and luck.

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Tone & Style

Witty, honest, deeply personal, and quietly motivational—this conversation blends humor with vulnerability, storytelling with actionable advice, and the relaxed banter of old friends.

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For the Listener

This episode is perfect for:

• Anyone feeling “lost” in their 20s or beyond
• Fans of Conan O’Brien’s backstory and approach to life
• Listeners craving relatable stories about family, persistence, and redefining success
• Those looking for a lighthearted but honest take on growing up, aging, and evolving

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[End of Summary]

Transcript

[Conan O'Brien]

You and I are going to be hanging out a lot now.

[Craig Robinson]

Anytime you want to hang.

[Conan O'Brien]

I don't think that's true. Yeah.

[Craig Robinson]

Any.

[Conan O'Brien]

I think I'm going to start cold calling him True for you.

[Craig Robinson]

So here's the thing. When I come to, La Rey gets coated. When I. Let's hang, let's hang.

[Conan O'Brien]

Let's shoot some hoops.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

I'm going to drain some threes from 80 yards away that don't go anywhere near the bucket. Nowhere near.

[Chelsea Clinton]

I tell you.

[Craig Robinson]

That's the best you can. And then. And then I'll go to a the back alley comedy club with you.

[Conan O'Brien]

I think you would do better. You would do better at comedy than I would at basketball.

[Chelsea Clinton]

This episode is brought to you by Chase Home Lending.

[Craig Robinson]

Hey, little girl.

[Chelsea Clinton]

You look so dapper today.

[Craig Robinson]

So I was telling Julia, one of our producers, that this is one of my favorite jackets.

[Chelsea Clinton]

Yeah, I like that.

[Craig Robinson]

So I only wear it once a year on the show. I should wear it more often, but.

[Chelsea Clinton]

Or get another one. No, it only comes in gray.

[Craig Robinson]

No, they come in different colors, but I like this color.

[Chelsea Clinton]

Oh, you like the gray?

[Craig Robinson]

I like this gray. And.

[Chelsea Clinton]

Well, I think it would look good

[Craig Robinson]

in other colors, too, off camera.

[Chelsea Clinton]

Okay.

[Craig Robinson]

So it gets a lot of wear.

[Chelsea Clinton]

Okay, that's good. It gets a lot wear. It's good to know. It's good to know.

[Craig Robinson]

But. But it's not as hot as your leather outfit you got going on.

[Chelsea Clinton]

Well, actually, this isn't leather. It's sort of like a faux, faux leather. So they're actually more jeansy. They just have a finish. It's a jean finish. It's a sort of a wash that's over. Right. So this is really just a jean that gives the leather effect.

[Craig Robinson]

Got it.

[Conan O'Brien]

Got it.

[Chelsea Clinton]

So just so you know. And they're very comfortable, so you don't get this squishiness of the stiffness of the leather.

[Craig Robinson]

Yeah.

[Chelsea Clinton]

But thank you. Thank you for noticing. You're always put together, so we've hit a milestone.

[Craig Robinson]

It is just. It's amazing because it went by like that.

[Chelsea Clinton]

Yeah. It's been a year since we launched, imo.

[Craig Robinson]

I know.

[Chelsea Clinton]

So we finished our first year and we want to thank all our listeners, all the people on YouTube who have tuned in. It's so fun hearing everybody's comments and feedback. And, you know, my friends are always texting me with, I can't believe you said X, Y, or Z. And you run into people all the time.

[Craig Robinson]

I do. Cause I'm out here in the Streets. So I run into people all the time who are like, it is a fantastic show. You and your sister are so cute together. And we love the guests. And I also want to thank our staff, everybody here who helped.

[Chelsea Clinton]

Absolutely. We could produce this thing.

[Craig Robinson]

It is amazing. It's been a really neat ride. And I've said this many times on this show, being 60 years old and being able to learn something completely new around a young group of people where it's changed my aging. I feel like I'm aging backwards now that we're doing this.

[Chelsea Clinton]

It's the beauty of continued evolution in this phase of life. I say it all the time. It's like, you know, 60 doesn't mean what it used to.

[Craig Robinson]

Right.

[Chelsea Clinton]

When I start counting back to what 60 was, and I think about the fact that dandy grandma or grandparents were this age when we thought they were old, that's kind of a trip. But they kind of stopped. I mean, it's sort of like they push the, they push the pause button on life once they retired. And I just think, you know, the recreation of self and trying some new things I do think keeps you young.

[Craig Robinson]

Yeah, yeah. And obviously we miss mom and she's not here to see this, but we're doing exactly what she did. Right. She retires at the retirement age, waits about six months and then goes back to work.

[Chelsea Clinton]

Yeah, right.

[Craig Robinson]

Like, what are you doing? And she went right back to work, right in the same office. And I think that put some years on, added some years to her life.

[Chelsea Clinton]

So she would be proud of this project. She would get such a big kick out of listening to us go back and forth.

[Craig Robinson]

She'd be sitting in the back over there.

[Chelsea Clinton]

Woo.

[Craig Robinson]

Yeah.

[Chelsea Clinton]

Yeah. That would have been good having her here in the studio. But, you know, this show is a tribute to her because of the parenting that mom and dad gave us, because of the people that they were. And I think our relationship has always been strong, has remained strong. And a lot of the IMO's, the opinions we have come from, the wisdom they pass down to us, you know, I mean, it's a trip, people, I hear their voices so clearly in my head every day, guiding me and, you know, giving me the reassurance that I'm living life in a way that would make them proud. So it's fun to be able to share some of that advice with the listeners. And hopefully, I mean, that's what we hope is that when people listen to the show, they hear some of what we got to hear, you know, and that it's helping some people along the way. Cause that's really the goal here is, you know, to entertain, but to also, you know, share some wisdom along the way.

[Craig Robinson]

Yeah, it really is. When I'm in the airport or, you know, wherever I am, people stop me and they just say, boy, your parents must have been really great. And so that's the real. That's the real tribute for me.

[Chelsea Clinton]

And I also wanna make sure to thank all of our sponsors this year. Too many to name right now. We don't wanna take, but. And of course, the show would be nothing without great guests. And we have another great one for this episode.

[Craig Robinson]

Yeah, yeah.

[Chelsea Clinton]

Conan o'. Brien.

[Craig Robinson]

I know, I know. I'm at a little disadvantage. Cause you have a terrific relationship with him and I'm.

[Chelsea Clinton]

I feel very special that Conan is my friend.

[Craig Robinson]

Yeah, that's so sweet.

[Chelsea Clinton]

He's giggling over there. You are my friend, Conan.

[Craig Robinson]

I'm a little jealous of Conan because the way you talk about him being such a nice guy and doing things for you, it just sounds like me.

[Chelsea Clinton]

Are you jealous? That's probably why I like Conan, because he's a tall, friendly guy, just like my big brother.

[Craig Robinson]

Yes, he's saving, but I think he's

[Chelsea Clinton]

probably done a little more for me over the years than you have.

[Craig Robinson]

I know, I've been busy. I've been busy, I've been busy. Well, let me give just a couple of flowers here for Conan. As everyone knows, he's a television host, comedian, writer, producer. He hosted three late night talk shows, Late Night with Conan o', Brien, the Tonight show, and Conan, and is currently the host of the podcast Conan o' Brien Needs a Friend, which has one in me, which I have recently learned was the first podcast that you ever did.

[Chelsea Clinton]

So he was one of the ones I felt safe with in that early stage. Yeah.

[Craig Robinson]

And he will be hosting the 98th Academy Awards. So. Conan, come on down.

[Chelsea Clinton]

Hey, it's my friend Conan.

[Conan O'Brien]

Oh, we do. Oh, hi. How are you?

[Craig Robinson]

Well, you came in like you got work to do.

[Conan O'Brien]

Yeah, I just had a lot of sugar this morning, so I think you

[Chelsea Clinton]

probably have a lot of sugar every morning. I mean, it's not like you, you

[Conan O'Brien]

know, you know, it's funny. This is a true story. But I have always had a lot of manic energy. And about 10, 15 years ago, my doctor retired. So I went to see a brand new doctor for the first time and he's running me through the checklist, you know, of this, this, this just wants to get to know me. And he said he finally got to this one part of the checklist. And he said, now let's talk about drug use. And I said, I. Which is true. I'm never done drugs in my life. Never tried a drug, never wanted to get into that. So I said, I've never done any drugs. And he said, let me ask you again about your drug use. And I said, I've never done any drugs. And he said, what about cocaine? And I said, this is true. I said, no, you're making sense. No, no, this is 100% true. And I said, I've never done cocaine. And then he put his clipboard down and he said, this questionnaire doesn't work if you're not being honest with me. And I said, I'm being honest with you. And he said, I've senior work. And he just assumed that I'm all coped up. And I'm saying, this comes naturally.

[Chelsea Clinton]

For better or worse, I was born this way.

[Conan O'Brien]

Yeah, this is the way. I mention this a bunch, but my dad was a doctor and a scientist. And maybe after 15, 20 years of being on television, he looked at me and he wasn't trying to be funny, he just said, I think I understand you are making your living off of something that should probably be treated. And I said, I love you too, dad.

[Chelsea Clinton]

How old were you when he gave you that observation?

[Conan O'Brien]

Well, I was. I mean, I think he had seen me do the late night show. I mean, I might have been in my late 40s when he said that. Oh, my God, yes. This was not something he said to a. You know, this was him looking at the arc of my life and seeing that all of this nonsense that comes out of my head and the crazy energy. In another era, they would have treated me, you know, they would have put

[Craig Robinson]

me in a special.

[Conan O'Brien]

Admitted you. Admitted me?

[Craig Robinson]

Yes.

[Conan O'Brien]

That's the nicest thing you've said to me in a while. Put me in a facility of some kind. But now we live in this weird. I mean, it's all. When you're born, it's such luck. But in another era, my people in Ireland, you know, standing around and we're supposed to build a stone wall. I wouldn't have been helping with the stone wall. I'd have been off to the side doing bits and going, yeah, and then this guy, and then that. And they'd be saying, this idiot doesn't do anything.

[Chelsea Clinton]

Are you unique in your family? Cause you have a big family.

[Conan O'Brien]

Yeah, I'm one of six. I will say they're. My siblings are really nice. They're really smart. They're sweet.

[Chelsea Clinton]

Do they do drugs?

[Conan O'Brien]

No, they do not. I think we all should, but no, they don't. It is. I see a lot of similarities with my siblings. We all have sort of the same stuff, and it comes in different versions. They're very creative. They're all really funny. And then I just happen to match this particular time in history when we have television and podcasts and places where people like me can actually do this and put a roof over our head doing it, which I don't think existed. You know, it took just in the last hundred years for this to come along.

[Craig Robinson]

Well, you said they're all funny. Where does that come from? Were your parents funny? Was your kitchen table funny at dinner time?

[Conan O'Brien]

Yeah, everything starts at the kitchen table. For us, it was Sunday dinners. My mom always insisted that we all eat together. We have a Sunday meal after church, we come back, we sit around this round table, and we would have our meal, and then people would jockey for who's the funny one at the table and who can really make mom and dad laugh. And especially my dad, when he would laugh, Repressed Irish Catholics. And you see this thing that every culture has. What's the key where they're allowed to lose their control a bit. My parents didn't drink, obviously. There's no drugs. There's no. No one talked about sex. So there are all these areas that are off limits. But. But you're allowed to be funny and laugh, and you're allowed to eat tons of fried ham. And those are the areas where we're allowed to let our hair down. And so my dad, when he would laugh, my mom had a great laugh. My dad would hug himself, and he would kind of clap himself and hug himself and rub his hands together. And. Huge fan of you and the President. And I brought him to an event I did once in Washington, D.C. and he got his picture taken with you guys. And the president was so nice. He said, yeah, yeah. Hey, Conan. Dad, dad, get over here. And he made it all about my dad. And my dad for the next 15 years of his life. Just had the picture with you guys. And your daughters were kids then, but they were in the picture, too. And that was something. I think. I think he lived another 10 years because of that. Talked about it nonstop.

[Chelsea Clinton]

Oh, my gosh.

[Conan O'Brien]

So. But so much of my career was. I think it all began with trying to make the parents laugh.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

And that's where things start. And you can. Then later on, it can become, oh, I'm hosting the Oscars. Or I've got a late night show where I'm doing this big deal or that big deal, but it's really no different. You're still in some way trying to make them laugh.

[Craig Robinson]

Yeah.

[Conan O'Brien]

You know, and I think just like the two of you, you're probably for the rest of your life gonna be trying to live up to what your mom or your dad would want. And that stays with you. And I'm a big believer in we lose these people, but we don't lose them. Oh, for sure they're with you.

[Chelsea Clinton]

Oh, my gosh.

[Conan O'Brien]

And they're why you still, a lot of people would say you two are good. You're good. You can let your hair down now. You can. But you are trying to still live up to that standard. And I think that's what I'm trying to do with my parents.

[Craig Robinson]

Hey, Mish, you remember when we used to go on road trips and mom used to meticulously pack the trunk of car with plenty of food, like fried chicken?

[Chelsea Clinton]

And it never tasted better than in the backseat of a car, man, with

[Craig Robinson]

the coming out of the tinfoil, you know, it was really good. And it would pound cakes, cookies, the whole nine. And I remember it'd be a treat to even get flavored potato chips because, you know, mom would say, let's just get the plain ones. No barbecue, no salt and sour.

[Chelsea Clinton]

Not a lot of extras in the Robinson household.

[Craig Robinson]

No, no. But now, you know, the difference is night and day when I travel with my family. What do you think?

[Chelsea Clinton]

Yeah, I mean, you know, mom would have to pack for us, staying in a place a long time. So it wasn't just snacks for the car because you couldn't just get anything you wanted. So she had to come on vacation with everything she needed for the week, which seemed like a hassle.

[Craig Robinson]

Yeah, it was like we had the whole trunk of the car was a grocery store. Now, are you particular about your snacks? For example, I like my cheddar cheese, but I want it cut on blade number one.

[Chelsea Clinton]

Really?

[Craig Robinson]

What about you? Yeah, I like mine thin. I like my cheese cut sliced thin.

[Chelsea Clinton]

I don't think I'm that particular. I think a snack is a snack.

[Craig Robinson]

Well, now, when I travel with the family and we book a stay on Airbnb, I have the convenience of having our fridge stocked with our favorite snacks. Or anything we might forget or don't have.

[Chelsea Clinton]

We could have used that when we were little.

[Craig Robinson]

How about it? As a matter of fact, Kelly always uses Instacart when we're on vacation. But with this new Airbnb Instacart partnership. I love the convenience, this feature within Airbnb Services to order our groceries on Instacart. The partnership allows you to seamlessly book with your Airbnb reservation before or during your trip. I might do some cooking during my stay this time because our groceries will already be there when I arrive, making it feel like home from day one.

[Chelsea Clinton]

You're manic, you're silly, but you are Wiccan. Wicked smart.

[Conan O'Brien]

Oh.

[Chelsea Clinton]

I mean, yeah. And so was your family. I mean, I love hearing about the fact that your mom went back to law school. Can you talk about her?

[Conan O'Brien]

Yes.

[Chelsea Clinton]

She sounds. She's a badass, so.

[Conan O'Brien]

Both my parents were the first ones in their families to go to college. They. You know, everybody's got an immigrant story. Everybody comes from someplace else.

[Chelsea Clinton]

Yeah, let's say that again.

[Conan O'Brien]

Yeah, no, we. We all. I mean, I. Last night, I was trying some Oscar jokes out in a comedy club, and I took an Uber home, and the driver's from Jordan, and he recognized me. And we started chatting. We had the greatest chat on the long ride from East LA back to my house. And just a wonderful talk. And he put me on the phone. He said, can I call my daughter? And I said, sure. She's 25. So he's a Jordanian immigrant. His daughter is taking her mcat. She's gone to college. And I just was telling him this was our story, too. We came to this country late 19th century, and there was a lot of people not too thrilled to see the Irish in Boston. So my people moved out to the central Massachusetts and worked hard and I think had good values. And then my mother grew up in Worcester, Massachusetts. Her father directed traffic in downtown Worcester. One of the funniest people I've ever met. Remember my grandfather really well, we called him Hoofer. Cause he knew some dance moves, and so everyone called him Hoofer after, like.

[Chelsea Clinton]

And you got none of those genes?

[Conan O'Brien]

I didn't get those. Look, if I knew I was getting slammed on this show, jeez, I would not have been. Okay.

[Craig Robinson]

You don't have to take that from her.

[Conan O'Brien]

Apparently I do.

[Craig Robinson]

Yeah, you don't.

[Conan O'Brien]

Apparently I do. So. So my mother worked hard and she got a full scholarship because they didn't have. Her father earned $55 a week, so she didn't have that kind of money. She got a full scholarship to go to Vassar, which was a big deal. And then she went to Vassar, and when she graduates, she gets a full scholarship to go to Yale Law. School, she goes to Yale Law School. She leaves and she goes to a big law firm in Boston. She clerked for a state supreme court

[Chelsea Clinton]

justice, but she also raised. This was after she had kids, right?

[Conan O'Brien]

Well, before she had. It was before she had kids. And then she just started a law firm when she started to have kids. And then she had to take time

[Chelsea Clinton]

off because she had a lot of kids.

[Conan O'Brien]

She had a lot of kids.

[Chelsea Clinton]

You guys just kept coming and coming.

[Conan O'Brien]

I mean, I swear to God, I think she had a child every four months. Medical science is still trying to figure out how the Irish can do that. But, yeah, I think my brother Neil is 61, was born in 61, Luke in 62, me in 63, Kate in 64. I mean, no one ever knew my name in that house. And then there's Kate, Jane, Justin. And she went back to work and.

[Craig Robinson]

Wow. She went back to work after. So how old were you?

[Conan O'Brien]

I would say she went back to work when I was about, I want to say nine. I was not happy about that because I loved coming home and my mom was there, but she went back to work. But she had stories of the early days, early, you know, 1960s, when she is a graduate of Yale Law School and she's working at a big firm and she would go to a meeting with other lawyers and then they would take a break to go to lunch and they would all go into the dining room, but she couldn't go in because it's men only. And so I would ask her, did that make you angry? And she said, oh, no, it was just the way it was. And they set up. She said, they set up a card table for me. I sat outside and two of the lawyers were very nice and sat with me. And so there was this. I think it gets overlooked sometimes, but there's a thing that happens with people who are on the front line of change. They. Sometimes you think they're going to be angry, sometimes they're not because they think, I don't have time for this.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

I've got to win. I got to get the win. So she worked hard. She became a partner. And I think she was maybe the second or third woman to ever be a partner in this big law firm.

[Chelsea Clinton]

Well, you make a good point that. And I want young people to understand this because sometimes when change has happened and the younger generation doesn't know what it takes, they can be a bit judgmental about what it took. For those to the kind of mentality, the kind of. Because there's some Young women who say, well, why didn't you speak up and why didn't you use your voice or look at an older generation and say that, you know, you're allowing something to happen without understanding the context of the growth.

[Conan O'Brien]

Yes.

[Chelsea Clinton]

You know, and I think that's why sometimes we get in the way of change, because the younger people want it, think it should look different. They think the attitude should be different. And you just. Your mom knew what she knew. Being the first woman, the only woman to ever practice law and then to make partner, you know, what kind of compromises your mom had to make to get there. And she needed the job, too. She had six. How many of you all?

[Conan O'Brien]

I don't even know. I've tried to count my siblings, and there's just too more, too many. I can't do it. But the. Yeah, it reminds me a little bit of that. There's that Jackie Robinson ethos where, because he was the first, he felt he had to be completely above reproach in every.

[Chelsea Clinton]

I know a little bit about that.

[Conan O'Brien]

Yeah. Well, that's what I'm. That's what I'm saying is the. You know, I think I could tell when you and I took a trip once to visit a big, giant military base in the Middle east, and.

[Chelsea Clinton]

Which was an amazing trip.

[Conan O'Brien]

It was an amazing trip. I could tell that you and your team were being so careful, that everything is done by the book, that there's no, you know, that if, you know, there's no perks, there's no. And I was really impressed with that. And it occurred to me then, oh, I see. Everyone feels we need to be so. So, so far beyond.

[Chelsea Clinton]

It wasn't even a feeling. It was the truth.

[Craig Robinson]

It's the truth.

[Conan O'Brien]

Yeah.

[Chelsea Clinton]

You know, I mean, there's absolutely no way that the behavior in this current administration would have been accepted by the first black family in the White House. So fortunately, it wasn't difficult to do because we are those people. It wasn't difficult to follow rules. It wasn't difficult to have high standards. It wasn't very difficult because in order to get where we are, as you've seen and your mother, you don't get here without being damn near perfect. We don't get to fail 2, 3, 5, 7 times. We don't get to file bankruptcy over and over again and still be considered a successful business person.

[Conan O'Brien]

Right.

[Chelsea Clinton]

You know, we don't get to not be at the top of the class. You know, every. Every I has to be dotted, every T has to be crossed, and your mom was among the first to begin to pioneer that. Yeah, that firstness.

[Conan O'Brien]

Yeah. And I think because they, you know, the biggest game changer for Irish Catholics in my parents generation was John F. Kennedy. And you've got this very glamorous first family and they're Catholic and Irish. I think that made a huge difference for people in my parents generation and made a big difference for me because, um, it's. They made it cool. Yeah, they made it cool to be Irish and then I made it uncool speaking. When John Kennedy gave us, I took away.

[Craig Robinson]

Were you a cool kid growing up?

[Conan O'Brien]

God, no. Did you? How can you ask in his pictures? I wish.

[Craig Robinson]

You know why?

[Conan O'Brien]

Why would you ask that with a straight face?

[Craig Robinson]

Here's why. Here's why. When I first met you, you were surprised how tall I was. Yep. As I of you. Yep. And the first thing I thought, I'm sure he was an athlete in high school and one of the cool kids and funny in the locker room, that kind of thing. So I want to get that.

[Conan O'Brien]

Tell me about what happened. Let me explain what happened. Let me explain to you what happened, sir. I was. My height came late, so I was one of those guys who had a growth spurt kind of later in the game.

[Craig Robinson]

Okay.

[Conan O'Brien]

So I recently saw someone found footage of me in. When I'm 22, I'm just out of college and I think I look like a 14 year old.

[Craig Robinson]

Really?

[Conan O'Brien]

Yes. Of undetermined gender. And I look at that person and I think, you're 22.

[Chelsea Clinton]

So you weren't, you didn't get your height then?

[Conan O'Brien]

No, no, I had my height by then, but I was 6, 4 when I moved out to LA to start my career. I was 6ft 4 inches tall, I think 155 pounds.

[Craig Robinson]

Okay.

[Conan O'Brien]

Now I ask any engineer who's listening, do the math on that structure. It will collapse. It's gonna break, it's gonna go down, and if a moth lands on it, it will collapse. So there was no, you know, people sometimes say, cause I make fun of myself a lot. And they say, well, that's kind of an act. And I go, no, no, no. That comes from. I think obviously they know now your core personality is formed fairly early on. And then you, you do little finishing touches to it, but by the time you're 15, 16, 17, it's there. And those were years for me where I didn't feel I was not cool. I was not a good athlete. My brother Luke, who's a year older than me, is much smarter than me. My brother Neil was much stronger. And I just thought, I don't have anything to offer. I really thought that for a long time. And it took me a while. It took me a long time to kind of put it all together. Which is why when I say I find myself kind of ridiculous, it comes from a place of honesty. Like, that's. That was my personality growing up. And so I didn't. I was not. I was funny with my friends, but I was not the class clown. The class clown, I maintain, you know, usually ends up in, like, a motel shootout. You know, the class clown, the guy who gets up and changes the clock forward and is, you know, throwing stuff out the window. They're in prison. Soon after high school, I was not that guy. I was joking around with my friends. And then when the teacher came in, I was really quiet and a nerd. So that's my story.

[Chelsea Clinton]

And it got it. But it got you to Harvard.

[Craig Robinson]

Yep.

[Chelsea Clinton]

Which is where a lot of funny nerds go.

[Conan O'Brien]

Yeah, I didn't even. You know, the irony is, as a kid, I dreamed about being in show business, and I loved comedy. And that's how my dad and I really bonded. You know, you're always trying to, like.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

I think a lot of boys look at their dad and think, what's the. How do I key into this person? How do I. You know, he can be formidable. I'm not sure how I can really connect with this person. And then we would watch comedians together, we would watch comedic movies, and I would see him laugh. And that was where my interest started. And I started doing things and loving the idea of getting to do comedy. And then I thought, I'm in Boston, Massachusetts, Brookline. Nobody within a thousand miles is in show business. I've never seen anyone in show business. That's not a real thing. I gotta find another way. So I decided I want to go to a good college and make something of myself. So I'll just become a grind. It's not a glamorous story, but I was a grind. And I was grinding it out in my little room, memorizing things, and I.

[Chelsea Clinton]

What did you think you wanted to be?

[Conan O'Brien]

I thought, well, I'll be.

[Chelsea Clinton]

Oh, it's a pursuit.

[Conan O'Brien]

I will be a serious person. I'll be a, you know, editor of a newspaper, or I'll be an actor.

[Chelsea Clinton]

What'd you major?

[Conan O'Brien]

I was. I was. Loved English. I was a history and literature major. And I thought, that's what I'll do. So I get to. I achieve that goal, I get into Harvard. Didn't think I was going to. I did. I think now it's time to become the serious man of letters. And someone said, I'm gonna go to this meeting of something called the Lampoon. And I said, I've heard of that. That's pretty famous. Yep. And I said, maybe I'll tag along.

[Chelsea Clinton]

Was this first year.

[Conan O'Brien]

This was first semester freshman year. I was at Harvard for two maybe weeks. And so I went and there's this kooky little building there, and I sat on the floor and they come in and we're all sitting on the floor and they talked to us and they said, it's very competitive, but you all have to submit funny stuff, and we'll see what happens. And I said, I'll give it a try. And made it through the first cut, made it past the second cut, made it through some other things, and then the next thing you know, I'm a first semester freshman and I'm on the Lampoon.

[Chelsea Clinton]

And that's.

[Conan O'Brien]

I was hooked.

[Chelsea Clinton]

Let me just explain to the listeners, I equate the Lampoon to, like the Harvard Law Review of Comedy. I mean, it is considered.

[Conan O'Brien]

It's very flattering, but it is. Well, it was a huge deal. And so many famous funny people and great writer John Updike had been on the Lampoon and, you know, Robert Benchley and the guys that created National Lampoon and did Animal House, and I mean, it all came. All this great stuff came out of the Lampoon.

[Chelsea Clinton]

And it was unusual to be selected as a freshman, I think.

[Conan O'Brien]

Yeah, it was a little bit unusual. And then I gave my whole life to it. You know, it was one of those things where I felt like I had a calling.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

Up until that point in my life, I thought anything that I achieved. And this is very Catholic, but I'm sure it's not just Catholic. It's tons of religions and cultures. I thought, anything good has to come through suffering.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

So I really suffered to do well on the test. I really suffered. I really suffered. I was. Had a lot of anxiety. And then I would do well on the test because I suffered. This was the first time in my life that I would say, hey, here, what about this? And people would say, that's great. And I'd say, really?

[Chelsea Clinton]

That was easy.

[Conan O'Brien]

That was the. That was easy. I had fun. Wait a minute. I had fun. Didn't take a lot of time. And now people are reading it and laughing and I'm getting that same dopamine hit I get when I make my dad or my mom, laugh. What's this all about? And then I was hooked. I mean, I said, I don't do drugs, but this is, to me, the most powerful drug. And it goes for all of us. When you find that thing that gives you joy, and then you realize that, you know, in the. You know, whatever. Hundreds and hundreds of years ago, people thought the greatest thing would be able to turn, you know, lead into gold. I think the closest thing I've seen to that in life is when you can do something that gives you joy, but it gives other people joy, too. And then someone hands you $20 afterwards, a check. I hope it's more than $20, but

[Chelsea Clinton]

maybe that's just a little bit more than you'll make for the Oscars.

[Conan O'Brien]

Yeah. Probably haven't even looked into that yet, but I'm sure I'll lose money. But that is, to me, that is magic. In our time is when you can do something that. And you've both experienced this, where, wait a minute. I'm having fun. I'm doing what I think I was put here to do, and other people are thanking me. That's insane. So that, to me, was when I got that first hit. And really, everything has just been an extension of that. When I called my parents senior year and I said, I have to give this comedy thing a try. And I talked to them as if I was becoming a monk. I said, look, there's probably no money in it. And they were, no one will marry me. Yeah, no one will marry me. And that was true for a long time. And then, you know, it. It's really just all that happened then. And then everything else has just been moving the little chess piece a little further forward. And now I'm here talking to the two of you. So that's the miracle of it all.

[Craig Robinson]

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[Chelsea Clinton]

After Harvard did you immediately you were able to.

[Conan O'Brien]

I had a good friend in school. I knew that the thing I had to do was go out to la, that we had to go, that I needed to go out to la, but not New York. Why LA versus New York? Wasn't a lot of work in New York.

[Chelsea Clinton]

Okay?

[Conan O'Brien]

There really wasn't a lot of work in New York and a lot of the work was in la. And so I said to a really good friend of mine in college, Greg Daniels, who went on to create, I mean most of the great TV shows of the last 25 years, the Office, Parks and Recreation, King of the Hill, I mean co create that and he's you know, just had this huge career, but at the time were two pretty nerdy guys, and we were newly 22 years old. And I said, do you want to do this with me? And one of the things that was really key was he was. Greg's a really funny guy, but he was also like an ethical, good person. And I thought, I don't want to go out there without a friend who's with me, who I know to be a really high quality person. And, yeah, rule number one is gotta be funny. And he's clearly, you know, hilariously funny, but also really good work ethic and a good person. So we went out together and, you know, we started. We got some work on a show called Not Necessarily the News, which was on hbo. And this is HBO back when, if you wanted to watch the show, I think in those days I'd have to tell my parents, you need to go check into a motel. Hey, check out my show. What's it on? Is it on NBC? Yeah, you need to go to a motel. And yeah, it was like I was working in porno or something. Let's clean that up. Anyway, it was. It was. But it was a start. We got started, and then the first time.

[Chelsea Clinton]

And earning a salary, Earning a salary.

[Craig Robinson]

Earning a salary right away, because the comedians we have on and the performers, they all go out. Yeah. Would do the same thing, but they're struggling for a period of time.

[Conan O'Brien]

We were lucky we got that gig right away. I knew I wanted to perform, so I started going to do improv at night.

[Craig Robinson]

Wow.

[Conan O'Brien]

And so I would work in the day and write, and then I would go to these little places where you put a $10 bill in a jar, and then you get up and you do improvisational scenes with other people. And my first time that I went to an improv class, I noticed, like, I was looking at everyone else. Cause it's the same thing if you're an athlete. Whatever you're doing, you look around and you. You try. And I size up, size up people. And who's the one who's like, okay, they're good, they're good. I walk into this place that's on La Cienega Coronet Theater, and it's this tiny little room, and there's a teacher there, Cynthia Segetti, and you put your money in the jar, and then you get up, and she had us doing different exercises. And I'm looking around the room and I'm going, no, no, no, no. Who is that? She's good. She's really funny. And her name was Lisa Kudrow. Going on to be in Friends. And I didn't know this, but at the time, she's looking around the room doing the same thing.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

And she's like, okay, that guy. The guy that's 155 pounds.

[Chelsea Clinton]

I was like, I was gonna ask,

[Conan O'Brien]

how much did you weigh? Then I weighed 156.

[Chelsea Clinton]

Okay. All right.

[Conan O'Brien]

I had a bagel. And so then I started working with her, and we became really good friends, and I started meeting other people. Then we lost the job that we had because they had to downscale the staff. So I think Greg taught SAT prep, and I went to work for Wilson's House of Suede and Leather.

[Chelsea Clinton]

Really?

[Craig Robinson]

Yeah.

[Chelsea Clinton]

That's true.

[Conan O'Brien]

And it wasn't even.

[Craig Robinson]

I have to check.

[Conan O'Brien]

They wouldn't. No, no. I'm telling you.

[Chelsea Clinton]

Of all the shops.

[Craig Robinson]

Yeah.

[Chelsea Clinton]

You picked Wilson's House of Suede and Leather.

[Conan O'Brien]

You know, I just want to get. I want to give them a plug. I think I went to a temp agency and they assigned me there, and they didn't put me on the floor. Floor, because I did not look like a guy who could pull off any kind of leather. So they put me, like, in an office situation. And I wasn't too happy during that period of my life. But then we got another gig, and then we end up on Saturday Night Live. So we move back to New York, and then I go to the sixth.

[Chelsea Clinton]

So you end up writing for.

[Conan O'Brien]

I'm writing. And then. And then I'm on the Simpsons. And then I was always the writer who would get up on a table and act things out and make the other writers laugh. And so when it came time to find someone to replace David Letterman on his late night show, I had worked for Lorne Michaels, and I give him all the credit. He told NBC, have you thought about this guy Conan? And they said, the writer? Yeah. And with the hair and the weird name. And he said, you know, I'm just. And they said, well, Lauren, if you'll vouch for him, he can audition. And so I auditioned, and I had a really good audition because I didn't think I had a chance.

[Craig Robinson]

That's always the way.

[Conan O'Brien]

And so I thought, I'm never getting this. This is the biggest star on television. Next. You know, I'm going to replace him. And I'm just this guy who's 29 years old. I'm still, you know, like, oh, there's a. My skin broke out again. It's still happening. And then I just went into that audition and had a blast.

[Chelsea Clinton]

What do you think prepared you? I mean, I think late night talk show hosting is one of the hardest things. I mean, it's just hard being on the show.

[Conan O'Brien]

I think what helped me the most is at the time, people said, you need to be a standup comic, which I had never done. I'd done a lot of improv. They said, you have to be a standup comic to be a late night host. And I found that the improv training is all about looking at people and listening and looking for what's funny organically. So I found that to be hugely helpful.

[Craig Robinson]

I've heard you talk about being able to take advantage of all the great luck that you had, and that warms my heart. Because as a coach and as a player, as an athlete, you're always taught that the most prepared person is also the luckiest.

[Conan O'Brien]

Yeah, yeah, yeah. It's that old saying, you make your luck. I think, first of all, I got just the time in which I was born. I am a poster child for incredible luck. I've been very, very lucky, and I give it up for that. I also know that I work really hard and I prepare and I try to treat people the right way, But I get very angry when people don't give it up for luck. And I'm also really aware that as a, you know, what was my path like as a white male coming up in the 1980s, 90s, a lot easier than a lot of other people in comedy and probably in any profession. So take a second. Give it up for that. Don't have an attitude about it. Be grateful. And then.

[Chelsea Clinton]

And then don't shut the door on everybody else.

[Conan O'Brien]

Oh, no. Shut the door shut. I disagree completely. Shut that door and nail it shut. Once you get in, don't let anybody else in. That's the message of this episode. Yeah, no, exactly. Yeah. And that's one of the things. I mean, I noticed it today. I show up and you've got all these great young people. There's great music playing. Everyone's. Everyone looks like they're 20, 21, 22. And I get.

[Chelsea Clinton]

Except for Dan.

[Conan O'Brien]

Except for Dan. Yeah, Dan. And listen, you served your country in the Korean War, and we appreciate it. 110 years old, but I feel I get so much energy from young people. And whenever. When I see young people that are really funny, I choose not to be threatened. I choose to be excited. This is this person, this guy, this girl. This person is great. They're terrific. They really make me laugh. I want to Enjoy them. I want to try and help if I can and just. Just anything. People. I know your. Your husband feels the same way, but I'm always preaching optimism to my people and I. And cautious optimism. I always say I'm like a 51, 52% optimist. But I do say the world has always been filled with horribleness. There's always been trouble. And this. When young people preach to me it's all over, or say it's the end of the world, or I just say, you have to understand this is the way it's always been and this is how it feels. And it reminds me of this great scene in the movie, the African Queen. Humphrey Bogart, Katharine Hepburn. They're in this boat. They're lost in the weeds. It's a great metaphor for life. They're trying to get out. They're trying to get out. He's pulling the boat with a rope. He's covered in leeches. He gets back in the boat and finally he gives up. And she gives up. And he says, we're never getting out of these weeds with this boat. We're never getting out of here. And they give up. And they say, we're just going to die now. And the camera starts to. They kind of pass out and the camera slowly pulls up. And you see it starts to rain. And you see that their boat is about 15ft from a massive river. They just don't know it. And then the water rises. And when they wake up in the morning, they're on the river and they're safe. And I always think about that. I think There've been probably 35 times in my life when I thought dead on the boat. I thought I was on the boat. And I'm dead on the boat. Not gonna make it through. I'm not gonna get to the college I wanna go to. It's over now I'm in the college, but I'm not gonna. I made that, but I'm not gonna get the career. Then you get part of it. Oh, no. I've got this late night show, but critics hate me. And everyone says this was a mistake. This kid who gave him this job, there's no way I'm gonna make it. Everyone's saying, you'll make it a few months, but then you're out. And then I make it past that. But then later on I get the Tonight show and I think, now I'm in good shape. Nope, that blows up. And I thought, now it's really over. No, it's not. It keeps happening. Over and over and over again. And then it's just learning to roll with it. To roll with it and say, okay, what's my next opportunity? Reset, recommit, and look for the next opportunity. And that is something I try to impart to my.

[Craig Robinson]

My mom really liked meeting you.

[Conan O'Brien]

Oh, that's nice.

[Craig Robinson]

She really liked meeting you. So we, you know, and I used to. I live a train ride away from her, so I'd visit her all the time and we talked about. Oh, yeah, it was really fun getting together and seeing. But that Conan, he was just such a nice.

[Conan O'Brien]

He's nice.

[Craig Robinson]

So you should. You should know that.

[Conan O'Brien]

Oh, well, that's huge for me.

[Chelsea Clinton]

That must have helped you land a beautiful wife.

[Conan O'Brien]

I don't know what I did. I just got. Yeah, my wife Liza is pretty incredible.

[Chelsea Clinton]

And how'd you guys meet?

[Conan O'Brien]

We met. I was. I was out doing a field piece and how those work is. There's a silly idea. I say, okay, I'll do it. And then I show up someplace and we. We shoot.

[Chelsea Clinton]

Which cameras was it? Were you in it?

[Conan O'Brien]

I was in it. It was a bit where. It's a long story, but there was a really. We decided it'd be very funny if I went to a top advertising agency and pitched a terrible idea.

[Chelsea Clinton]

I just love that I was.

[Conan O'Brien]

That I was.

[Chelsea Clinton]

And.

[Conan O'Brien]

And you know, my favorite spot is me being very confident about something that's really stupid.

[Craig Robinson]

Okay.

[Conan O'Brien]

And so I went. And so it was my idea. Wasn't my idea, it was someone else's idea. But my job was to go in there and go, let me tell you something. And these are the. These are the people that do like, you know, Air Jordan ads, the best of the best in the room. And I'm supposed to go in and pitch them the worst idea and have total confidence in it and almost treat them with contempt if they don't get what I'm saying. So I go into this room and I start doing my thing. I do. And I do one person. One person, one person. And then I start talking to this woman and I immediately stopped being funny. And I just start saying, oh, so. Oh, okay, so you. And did you write a. So, oh, I see. So you got your degree and. Huh. And then she went, yeah. And I was like, no, no, no, we'll see. Yeah. But what I did was I studied this, but then I did that. And we were just talking about the most mundane stuff. It wasn't comedy. I wasn't even trying to be funny. And my producers, the headsets on what is happening.

[Chelsea Clinton]

They're like, what's he doing?

[Conan O'Brien]

What's he doing? This is death. What's he doing? And then we chatted for a long time. And then I finished up the segment and then I. My head writer, Mike Sweeney, who's still my head writer and working with me on the Oscars and does an amazing job. But he was like, what was that all about? And then I said, I don't know, but maybe we should get everyone's contact information. And he said, why would we need their contact information? And I said, I don't know, Editing. He's like, that doesn't make any sense. Editing. What are you talking about? But the next thing you know, we just start. It's. We just start talking on the phone.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

So we didn't even have a set. We didn't. That's not even a date. We just met and then I just, we just talked on the phone.

[Chelsea Clinton]

How old were you?

[Conan O'Brien]

I was. Would I be 35 maybe? I was no spring chicken.

[Craig Robinson]

So you completely ruined the bit because you.

[Conan O'Brien]

They fell in love. They salvaged the bit. But you know what's great? You can look it up. You can say, Conan meets his wife. Conan meets Liza. And you can see me, I look still like, you know, now. I, I was 35, so I look like a 20 year old girl. And. And I'm there going, oh, hey, how are you? And you can see us talking to each other. And it's online and I'm gonna watch it. I never watched it. Cause I know what the real experience was, but I don't want to see it. But we ended up, you know, dating and then we got married and kids and it's been. I think we got married in 2002. So I didn't go to a good school. I can't do the math.

[Chelsea Clinton]

Yeah, I'm not even trying to.

[Craig Robinson]

Neat story.

[Conan O'Brien]

It's a great. Yeah. And it was really nice. And you know, it's crazy. Liza's mom watched it at home. She stayed up and watched it at home. Her dad was like, I'm going to bed. I don't need to see. And she was like, our daughter is going to be on national television. The Bits airing tonight. He didn't know anything about us. You know, we hadn't even chatted yet. We had, we had met, but that was it. We hadn't even talked on the phone yet. But Pam, my wife's mom, she stayed up and she watched it. And in the morning she said to Jake, unless that guy's an ax, Murderer. He's gonna be our son in law.

[Craig Robinson]

No way.

[Conan O'Brien]

And they said. She said that to more than one person.

[Chelsea Clinton]

Wow.

[Conan O'Brien]

And they said, what are you talking about? That TV show host who had a brief exchange with your daughter is gonna be your son in law. And she went, I just think that's what's gonna happen.

[Chelsea Clinton]

Wow.

[Conan O'Brien]

And happened.

[Chelsea Clinton]

Oh, she knew. She knew. And I know that Liza just lost her mom.

[Conan O'Brien]

Yeah, she just lost her mom. Sorry. But. Well, you guys have been through it too. It's just one of those. It's too profound to even contemplate. But I think the thing that is some consolation is we. These people are with us. They're in us.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

We didn't lose them. And I really believe that. And you don't even have to be spiritual to believe that. They imprinted on us and they're with us. So you're always gonna have your mom. I'm always gonna have my parents. Liza's always gonna have her mom. They live on through us. We just lost Catherine o', Hara, who is one of the, you know, maybe possibly one of the. I mean, not possibly, but one of the great, great, great, great comedic actresses of all time. And at the same time, one of the best people. Just a lovely, lovely person. And talk about walking the walk. She really showed up for everybody. And Martin Short gave the eulogy and he just said, she's with us. We didn't lose her. She's with all of us. She imprinted and her work is with all of us. And so that's what I take away from that.

[Chelsea Clinton]

And sometimes I literally. My mom comes out of my mouth, you know, And I'm noticing it more and more when I say something. I was like, that was Mom.

[Conan O'Brien]

Yeah, yeah, yeah.

[Chelsea Clinton]

It's like I even hear it. I was like, oh, my God. She just. Yeah, yeah, yeah, yeah. So.

[Conan O'Brien]

So.

[Craig Robinson]

Well, I want to talk about the Oscars, because you said something right when you came out that you went to do. You went to a comedy club to try something out. Can you talk about that whole process to somebody like me who's sort of not in the. And probably our listeners who don't get a chance to talk to someone else.

[Conan O'Brien]

If you explain to me how to be an athlete, then I can do that. I can do that. If you would work with me for a five year period.

[Craig Robinson]

Listen, I love developing talents. Okay?

[Conan O'Brien]

Well, I have no talent in that area, so good luck to you.

[Craig Robinson]

I'll have you making shots in.

[Conan O'Brien]

Oh, really?

[Craig Robinson]

Two weeks.

[Conan O'Brien]

Yeah, two weeks.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

Really I like to be that guy that's way, way outside taking up crazy three point shots that don't go near, but with total confidence. And I love to shout stuff out when I'm doing it.

[Chelsea Clinton]

And a freeze.

[Conan O'Brien]

Yeah, and then freeze and do that look of like, deal with it. And it doesn't even hit the rim. It misses the back part.

[Chelsea Clinton]

Okay, that's the next bit.

[Conan O'Brien]

That's the next bit.

[Craig Robinson]

Yeah, that's it. Where you have a coach who's working with you for weeks and you don't have to get you to make a shit.

[Chelsea Clinton]

That's all you do.

[Conan O'Brien]

I did this. I did a thing with Magic Johnson. We shot a thing where I think we played a game of horse together. And I'm just being such a clown. But he was so funny making fun of me, the way I shot, the way I moved. He starts to imitate me at some point. That was a dream come true. The Oscars, one of the. There's a lot of different parts of it and you start thinking about different bits and what could we do for pre tapes? What could we do? What kind of production number could we have? But you're always thinking about jokes. What could the jokes be? And you really want to test them. And one of the ways to do that is to go out to clubs. And what I like to do is go way, way, way start way far out. So we went to Covina, which is way out there. I mean, I think I was driving for almost an hour, got to Covina. And you go into a club and you're a surprise. And then you read a bunch of Oscar jokes. And it's fun because you make them part of it. You say, look, if you guys laugh at a joke that isn't good, that might convince me to do it. And then I'm gonna die on the Oscars, so don't do that to me. So they're laughing at the part where you're not even reading the joke. Yeah, yeah, I love that. And I've gone to a couple of clubs like that. I did one last night. And you just go way out there. All of them are same. They're the same in that you're in some back room or an alley standing around with other comics and you. This is a lesson I've learned again and again and again, which I actually find kind of filled with hope, which is, you think you've gotten to this other level where it's like, well, I'm hosting the Oscars and I'm gonna walk out at the top and have a tuxedo. But I'm in covina in an alley, and I'm hanging out, and someone's got a ventriloquist dummy. And I'm waiting for my, you know, I'm waiting for my turn to go out there.

[Chelsea Clinton]

Did you.

[Craig Robinson]

You did that on purpose?

[Conan O'Brien]

No, I didn't. I did not.

[Craig Robinson]

Who told him what?

[Conan O'Brien]

I don't know what we're talking about.

[Chelsea Clinton]

Craig loves ventriloquism.

[Conan O'Brien]

I honestly. I swear to you. I swear to you.

[Craig Robinson]

I don't trust you. You're too funny.

[Chelsea Clinton]

He. We've been talking about this.

[Conan O'Brien]

I honestly don't know what you're talking about.

[Craig Robinson]

You don't?

[Conan O'Brien]

I do not.

[Chelsea Clinton]

He. He is, I think, the last person who believes that ventriloquism is a lost

[Craig Robinson]

art is an underutilized vehicle.

[Conan O'Brien]

When you see a good ventriloquist, it is really funny.

[Craig Robinson]

How about it?

[Conan O'Brien]

And I'm. I'm going to side with you on this. When you see a really good one, it's really funny.

[Craig Robinson]

It's so funny.

[Conan O'Brien]

See?

[Chelsea Clinton]

Okay.

[Craig Robinson]

Did you put him up to this?

[Conan O'Brien]

No, I didn't. No, no, listen, I'm telling you something. I don't know anything about this. You're linked to ventriloquism. I swear to you. I swear to you. I would tell you right now, but no one said, hey, you don't want to get crying, mention ventriloquism. I did not do that. I just mentioned, like, that's how kooky it is when you're in the alley.

[Craig Robinson]

It is.

[Conan O'Brien]

And I love that. I love that you. It's this constant dance between put on the tuxedo and you're in an alley in a T shirt and jeans.

[Chelsea Clinton]

Do your nerves get. I mean, I mean, I watch you walk on stage to this audience of every famous person on earth. And, you know, they're not a regular audience.

[Conan O'Brien]

They're not a regular audience.

[Chelsea Clinton]

They're nervous. They're looking at themselves.

[Conan O'Brien]

They're very self involved.

[Chelsea Clinton]

Self involved and self conscious. And you're out there to be funny. I mean, does that change the nature of.

[Conan O'Brien]

It's a very different. It's a very different audience. Like when we would do the White House correspondence dinner, and I did that once under your administration, and I remembered I got to sit with you and it was really fun because, you know, you were so nice to me that night. We're sitting up on the dais, but that is not a normal crowd. That is a crowd of people that think they're the coolest People in the world. And they're there, they're thinking a lot about their own world. And you need to be funny, but you can't act like you know too much because then they'll resent you for that or think you don't belong. And so everything is this incredible long period of preparation to gauge what's gonna work in that room that doesn't go too far this way, doesn't go too far that way. And then I've talked to your husband about this. They make you follow the leader of the free world. He goes first. Right.

[Chelsea Clinton]

Really?

[Conan O'Brien]

And kills it. And then before they're still.

[Chelsea Clinton]

Well, usually they don't.

[Conan O'Brien]

Yeah. Yeah.

[Chelsea Clinton]

Well, I know the format usually works in the best interests of the host.

[Conan O'Brien]

The president we're discussing. Unusually good at that. And then he would finish, like, drop the mic, crowd going crazy. And a voice would go, President John McConnell, Bryan. And you're like, well, that's it. And you're walking up and you see people like, what? Who would go now? And so you gotta wade through that a little bit. But it's all calculating for what's the assignment. And the assignment is with the Oscars, like the White House Correspondents Dinner is think about that room and calculate. It's not. You're not at a club where they are there to get a drink, and then suddenly you pop up and they're really thrilled. They're not. You know, if you go to a high school and they're just losing their mind that you show up, that's a very different crowd than now. I'm gonna speak to a bunch of, you know, a list people who don't really like to give it up for anybody, but it's all just a calculation. You gotta calculate and then have fun.

[Chelsea Clinton]

Do you like that risk? Does it feel like, you know, I know how to be. I know. Like this is you on some high wire. Do you feel. Does it.

[Conan O'Brien]

Is it a text for you? I think I must like that to some degree. Cause I keep signing up for things like that. And so that's a problem. And when it's 3 o' clock in the morning and I can't sleep, um, Liza's like, maybe we don't do another one of these, but. But I do. Like, I think the trick is to. I figured out a long time ago if I'm having a good time, it. Things tend to go well.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

It's almost unheard of for me to have a really good time up in front of people. And people afterwards say, well, that was Awful if I'm enjoying myself. So I just keep trying to think of things. I want to tell a joke I really like. Now, they may not like it, but if I really like it, you will crack yourself up. I will crack myself up. And then I'm like, okay, well, you know, this job didn't pay much anyway, so I had a good time. And that's kind of my mission is I want to think of things and do things that I enjoy. And I think instinctively. We like to watch people having fun. We like to watch athletes who are having fun. You know, they're really like, when they're playing well, they are enjoying themselves. It's fun to play at that level. It's fun to give a great speech. It's fun to be up in front of people doing what you feel you were put here to do. So that that part I really like. And it's just doubling down on that. How do I figure out and if something starts to develop and I think I don't really like doing this. Cut it, don't do it.

[Chelsea Clinton]

Do you feel like comedy is more fraught these days? I mean, it just, you know. Yeah, I think it's talk show host or, you know.

[Conan O'Brien]

Yeah, I mean, I obviously I friends with the other the hosts. I'm not a late night host anymore, but I'm friends with them and I think they're all very talented. They're really good people and they're in a tough situation because of, you know, your job is to go out and talk about the news every day. And I was never, you know, strictly a comedian that live off the news or did. You know, I usually tried to find things that were silly and funny outside of the news, but we also had to do the news and things are so divisive right now. And I think it's gotta be just a really tough task.

[Chelsea Clinton]

Yeah.

[Conan O'Brien]

And I do have empathy for people who are trying to figure out what's funny in this because I know just as a citizen, I get up in the morning and I look at what happened in the news. My first instinct, I like to be funny. But my first instinct when I read the news is nothing here gives me joy or is making me laugh that hard and that makes me think of ideas outside of the news about everyday life or something. There's a weird ad on TV that cracks me up. Those are the things that I probably look for. But if you're doing one of those shows, how do you not talk about it? And then how do you not wear your heart on your Sleeve and maybe get mad or, you know, so it's difficult. It's difficult.

[Craig Robinson]

On our show, we have an audience question, a listener question. But before we get to the listener question, I need some development. You've been in the podcast business for a long time.

[Conan O'Brien]

It feels. Well, actually, no, not that long, but,

[Craig Robinson]

yeah, I guess kind of like longer than imo.

[Conan O'Brien]

Yes. Okay. Yes.

[Craig Robinson]

Any tips? Any best practices? What is it about the podcast that you like doing that might be helpful to a. I won't say young, but fledgling podcaster like myself?

[Conan O'Brien]

You are younger than me.

[Craig Robinson]

No, I'm older than you.

[Chelsea Clinton]

Yeah, he's my big brother.

[Craig Robinson]

Yeah.

[Conan O'Brien]

You're older than us.

[Craig Robinson]

I'm older than you.

[Chelsea Clinton]

He's an old man.

[Craig Robinson]

I was probably on campus when you were on campus. I was probably over in the gym playing your basketball team when you were a freshman. Yeah. Yeah. So I'm older than you are.

[Conan O'Brien]

So you were in the gym playing real sports when I was.

[Craig Robinson]

You were at the Lampoon.

[Conan O'Brien]

I was in a weird castle

[Craig Robinson]

on

[Conan O'Brien]

Arbor street thinking of something weird and giggling.

[Craig Robinson]

Yeah.

[Chelsea Clinton]

See?

[Craig Robinson]

And I probably was prefer.

[Conan O'Brien]

And who's cool? He asked me, you know, who's the cool one? Really? Yeah. Wow, that's incredible. I thought you were maybe 32 years old.

[Craig Robinson]

Incredible. Yeah. Thanks.

[Conan O'Brien]

And a ventriloquist.

[Craig Robinson]

Budding ventriloquist.

[Conan O'Brien]

Ventriloquist. I'm with you on that. I'm going to help you. I'm going to find you the right dummy. I'm going to get you a good one. I'm going to get you a teacher, too, because I want to see you do it.

[Chelsea Clinton]

Please.

[Conan O'Brien]

I think. Oh, I mean, I don't know the answer. I know it works for me, which is. And you're doing it great. Snacks out there. It starts with the snacks. It ends with the snacks.

[Craig Robinson]

Okay.

[Conan O'Brien]

Don't let this one too many kale chips. You know, you got to have some good. And some of them have to be bad for you. No kale chips. No high fructose this or that. No, you want to have.

[Craig Robinson]

You've got that.

[Conan O'Brien]

You've got good snacks. There's a really good vibe here. Like, it's fun to come here. And I think that's a big thing. You want people to come into the store and want to walk around and check stuff out, and so that is all working. And you two know each other so well. You can finish each other's sentences, and there's a good bond here. So that's all good. And to me, it's like, I don't I mean, I think I'd be a fool to give you guys any advice on what to do that you're not doing. I mean, it'd be nice if I got an expensive gift on the way out. I'm just putting it out there. I'm working on that.

[Craig Robinson]

Okay.

[Conan O'Brien]

You know, I mean, like a watch, a good watch, like a Patek Philippe watch.

[Craig Robinson]

Here, you can have this.

[Conan O'Brien]

That watch weighs more than I do. I could drive that watch home. It looks like a car. No, I think, I mean, it's, it's all about enjoying yourself again. I'll go back to that. Same thing I said about the award show or doing a nightly show or anything else, which is talk about the, the things you want to talk about that you're passionate about. I think passion and authenticity works better than anything in this format. And you're doing it so I don't, you know, other than stop lying about your age. Come clean. You are a 32 year old man.

[Craig Robinson]

I am.

[Conan O'Brien]

You were born in 2005.

[Craig Robinson]

I am 63. Was soon to be 64 in April.

[Conan O'Brien]

April, wow.

[Chelsea Clinton]

He's my birthday. When's your birthday?

[Craig Robinson]

April 21st.

[Conan O'Brien]

I'm the 18th. I'll be 63 on the 18th.

[Craig Robinson]

Yeah.

[Conan O'Brien]

I like an April birthday. So do I. I like it.

[Chelsea Clinton]

What's so good about it?

[Craig Robinson]

Far enough away from the good.

[Chelsea Clinton]

What's so good about it?

[Craig Robinson]

You get far enough away from the holidays where when you get gifts, it feels good again.

[Conan O'Brien]

Yeah. Also, I grew up on the east Coast. Okay, you guys. I know, Midwest. It's starting to get nice.

[Craig Robinson]

Yes.

[Conan O'Brien]

And so I always associated my birthday with the sun. Wait a minute, here comes the sun. Sun is out for the first time in nine months and there's a little bit of joy. And some birds are chirping.

[Chelsea Clinton]

I like that smell of grass.

[Conan O'Brien]

Are you into horoscope stuff? Do you? I don't really.

[Craig Robinson]

I'm not.

[Conan O'Brien]

I'm not at all.

[Craig Robinson]

I'm not. Oh, I thought you were going to see.

[Conan O'Brien]

I'm not.

[Chelsea Clinton]

Well, all these young people are, so I probably know more than it because it's all about, oh, you're a Leo rising in a sun, moon to sleep. And I'm like, what?

[Conan O'Brien]

No. And then I ask them, they'll say things like, oh, that's so Aries. And I'll say, why? And they'll say, oh, because, you know, Aries is, you know, loves a challenge and loves to push themselves and is a ray of light. And then I'll read, well, what's A Taurus loves to really challenge themselves, full of goodness and light. And you're like, it's awesome.

[Chelsea Clinton]

And then if you say something else, then say, oh, you must be a cancer moon.

[Conan O'Brien]

Yes.

[Chelsea Clinton]

And it's like, okay, so now there's something for every aspect, you know? Cause there's moons and there's your sleeping sign. What are these?

[Craig Robinson]

There's only 12. It can't be that.

[Chelsea Clinton]

Everybody can't.

[Conan O'Brien]

Right?

[Chelsea Clinton]

Can't be that.

[Conan O'Brien]

Alienated your entire staff. I know they're listening right now. They don't get it.

[Chelsea Clinton]

And they also like manifesting everything.

[Conan O'Brien]

Well, that's Oprah's fault. We blame Oprah for that. You can manifest it. I can manifest all day and all night that I want to be an amazing basketball player. It's not happening. Or I'd like to be a male model. I'm going to manifest it. Not happening. There's so many things that I cannot manifest.

[Craig Robinson]

Right.

[Chelsea Clinton]

Well, let's get to our listener question, because get some advice.

[Jake (listener question)]

My name is Jake, and I'm from Indiana. And my question is, how do I overcome feeling lost in my career? I achieved my childhood dream job at 21. I had worked for it since 5th grade, but then I decided I just didn't like it enough to do it forever. At 25, I switched to a new job with good opportunity. But it's far from home, where I'm originally from, and I don't want to be here forever. I'm now 26, and I don't know what I want to do. I don't love the idea of going back to school because I'm not sure there's anything I'd love to study full time. I have ideas, but nothing concrete. And with this constantly evolving world, I feel stuck, lonely, and depressed as a result. Help.

[Chelsea Clinton]

26. This is what we were talking about.

[Conan O'Brien]

I know. I mean, this has been a big theme of this podcast. Not through design, but it just happened. But, you know, in the brief description, you listen to what Jake's achieved already, and it's really good, you know, and this is just one of the things that takes a long time to figure out. I do think that we're in a world now where you take constant snapshots of your life, and if the latest snapshot doesn't please you, you think things are really dire. And this is called being 26. I mean, it sounds to me like Jake is kind of ahead of the game, has already had a lot of success, has options, and now is wondering what to do. This is a feeling you're going to have now and then it's going to go away and you're going to have, you're going to have a period where you think you're back on track and then it's going to come up again and this feeling will revisit you. And that doesn't mean there's anything wrong with you. It means you're a person. And we all have that. And it's anyone who looks at you and thinks, well, she doesn't have any problems, she's a former first lady and she's just, she's got the world by the tail and it's just, you know, doesn't understand that you can have a really bad Thursday, you can have a really bad October, you can have a bad year, you can have a bad two years, you can, I mean, that is called being here. That's what. And no one escapes it. No one gets out of it. And I think young people like Jake put so much pressure on themselves and they forget that sometimes treading water is just fine. That's, you know, not every day has to be a sprint to the finish line. You can have periods of your life. I've had many of them where I think I'm not really getting anywhere. I'm treading water, but I'm not drowning.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

So I think try not to be too self critical, try not to be too tough on yourself and appreciate what you have and what you've already achieved and know that also 26, you're a baby. That's my answer.

[Chelsea Clinton]

It's a great answer. It's spot on. And Jake, it's like 26 is if you're lucky. And luck has a lot to do with it with this generation. They're going to live until their 90s. You know, assuming that we continue to have good health care, which this generation should care about, because that's going to play a role. But science is definitely on their side. We've learned a lot. You know, people are healthier, they're living longer. So let's just say if Jake is lucky, he's going to be here till he's 90. You know, that's like, I can do that. That's 70 more years, 70 more years to live a life and to figure it out. So the 20s and the 30s and I would even say now the four 80s are the period where you aren't gonna know. I mean, there are a handful of people, and they're rare that pick a thing at 18 or 22 and they get it right. It's their passion. They're good at it. And then there's a job. Right?

[Conan O'Brien]

Yeah.

[Chelsea Clinton]

That's not the norm. You know, that's. That's the exception. And again, with social media, he's probably seeing some of those people post. Look at me living my best life at 26. I've already a millionaire, and I've done this, and I have a boat. And I d. You know, that's not the norm. You know, it wasn't the case for me.

[Conan O'Brien]

Also, people don't always tell the truth.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

On social media. That's right.

[Chelsea Clinton]

Absolutely right.

[Conan O'Brien]

That may be someone else's boat. Exactly nine times a day I've done that. I've often taken photos of boats and said, check out my boat.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

I don't have a boat.

[Chelsea Clinton]

That's right.

[Craig Robinson]

You've often done that.

[Conan O'Brien]

No, I'm. I'm kidding. I. I'm going to start doing it because I just. I'm getting in the idea that that's. I'd be cool. Right. But no, I think that's. That's people.

[Chelsea Clinton]

There are going to be many lives. Many if. You know. And that's what you want out of life.

[Conan O'Brien]

Yeah.

[Chelsea Clinton]

You know, you want to keep evolving. You want to keep trying on new things. And, you know, I certainly did that. I thought I wanted to be a lawyer. Went to law school. Wrong about that. Didn't like that. That felt a little shocking, all that debt. And I was like, damn, I should have checked to see if I liked law before I did it. But I didn't. And so I left the law. And thank God I did, because it wasn't the profession for me. Thank God I had parents who didn't care about that, and they encouraged me and my brother. We went down a whole. Should have been a certain career path.

[Conan O'Brien]

Yeah.

[Chelsea Clinton]

And entered into it and said, whoa, this isn't me. And so I had to redefine it. I had to start looking around, asking questions, exploring, trying on new things. And that's when I learned that I love service. And I actually like working with people. I don't like reading documents and just writing memos. I like sort of living in life. I learned that about myself. And if I'd stayed in the law firm and become partner, I wouldn't have. I would probably figure that out because ultimately you do have to wake up, even if you pick a thing. I've met people who have been in a profession their entire lives just putting up with it because it paid the Bills. And then at 60 or 70, they find the thing that they care about, the work is waiting for you. That work of figuring yourself out, it's waiting for you.

[Conan O'Brien]

And so he's probably in it right now.

[Chelsea Clinton]

He's in it right now like a

[Conan O'Brien]

guy like Jake is. It's. You don't. You're not even aware. Some people think sometimes I'll talk to one of my kids and they'll say, oh, I, you know, I wasted time today. I've got this thing. But I didn't really. I didn't make a lot of progress on it today. And I'll say, I have found that often you're working and you're figuring things out when you don't even think you are.

[Craig Robinson]

Yeah, that's right.

[Conan O'Brien]

Because we have, you know, front part of our brain. We have all these. And then you have a part of your brain that's chewing on things while you don't even know it. So Jake might be figuring a lot of stuff out right now that's crucial, where he realizes I want to be an astronomer, you know, but that's still a year from now when he has that revelation. But it is working on him on some level.

[Craig Robinson]

It's funny you say that, Conan, because I was just watching something and I can't remember if it was PBS or it could have been on social media, but Neil Degrasse Tyson, the renowned scientist, who is very entertaining, but I really enjoy him. When he talks, I listen. And he said something that I had never heard before, that procrastinators are usually highly intelligent. Yeah. For the reason you said that they procrastinate because they wanna give their brain enough time to come up with the solution. And like you said, this could be happening with Jake right now.

[Conan O'Brien]

Oh, yeah.

[Chelsea Clinton]

Mm. Yeah.

[Conan O'Brien]

Yeah, I think that's true.

[Craig Robinson]

So hang in there, Jake. And you know, my sister and I talk about this all the time. Try stuff, try stuff, try on stuff, try on. Find your passion. And sometimes you don't find your passion, but you'll find something that's pretty interesting.

[Conan O'Brien]

Yeah. And there's no. I think a lot of young people don't realize that they have more room for error than they think they do. You can try something and wipe out, or it just doesn't go anywhere. No one's paying that much attention. And no one later on is gonna present you with, hey, wait a minute, I know you're a big success now, but remember when you tried to open that dry cleaning business and it didn't work 35 years ago or whatever. But no, that happened. I got out of it. I paid my debts, and then I tried this. Once you figure out what it is, you're not penalized. No one. There's not a referee there watching, blowing the whistle, saying, nope, you're out. You just made a mistake.

[Craig Robinson]

Yeah, life's over.

[Conan O'Brien]

It feels that way, but it's not happening.

[Craig Robinson]

Yeah, yeah, it's a great point.

[Chelsea Clinton]

Well, speaking of evolving, and hopefully that helps, Jake, you're still evolving. I mean, did you just have your acting debut? I mean, I watched. If I had legs, I'd kick you. It was.

[Conan O'Brien]

It's intense.

[Chelsea Clinton]

It's intense, but so good.

[Conan O'Brien]

She's. I mean, Rose Byrne is phenomenal.

[Chelsea Clinton]

She is amazing.

[Conan O'Brien]

Yeah, she's absolutely spectacular. And so. Yeah.

[Chelsea Clinton]

How was that for you? I mean, was that your first?

[Conan O'Brien]

More or less.

[Chelsea Clinton]

And you were serious?

[Conan O'Brien]

You were a. Yeah, it was a serious role. They sent me the script and I said, well, this is a great script, but this isn't really what I do. This guy's the complete opposite of me. The director met with me, Mary Bronstein, who wrote it, directed it, and she said, I really want you to do this. And I said, I don't think you should want me. You should get someone who really knows what to do with this. And she said, I really do think it's you. And I said, okay, I'm gonna try, but I give you permission to fire me at any point and we'll still be friends. And I said, and if I'm not? Cause I love Rose Byrne. I don't wanna let her down. I don't wanna get in the way of this amazing movie. Fire me, fire me, fire me. And even if you shoot with me and you wanna cut me out, cut me out. No hard feelings. So. But again, I did. I worked on it. I thought about it a lot. I worked on it. I.

[Chelsea Clinton]

You were good. You were incredibly believable. There was no sign of regular Cohen.

[Conan O'Brien]

Well, here's the disturbing part. The guy I play has no empathy. Everyone hates him and wants to kick him. And people were just so mad at my character. And it's worrying me that that's inside me. I may have let out the real me. Yeah, that's in there. And so. But it was. It was a real challenge. But I. And it was scary. But again, going back to, you know, the. The. The question we just got. I've gotten to a point in my life where I think, give it a shot. You know, there are things I know I shouldn't be doing. If Someone said, hey, fly this F16 fighter. Gee, I've never done it before, but you know, no one's going to penalize me if it doesn't work out. Yeah, you'll be killed. You might kill other people. I know there are a lot of things I shouldn't just give a try to, but this one, I really went off the belief of the director and it was a lot of fun. And I'm really proud of Rose. Cause she's nominated for best actress.

[Chelsea Clinton]

She's phenomenal. You've got Craig is not pop culture ready. I told him he has to be better.

[Craig Robinson]

That's not true.

[Chelsea Clinton]

In this job where pop culture is, he's got to watch movies.

[Conan O'Brien]

What do you. Well, what do you watch?

[Craig Robinson]

Turner classic movies.

[Conan O'Brien]

Oh, okay. All right.

[Craig Robinson]

I watch Turner classic movies. See, look, I like watching movies. It's hard to watch these new series that have part after part after part. I just.

[Conan O'Brien]

You can't keep up. And then, you know, I have a,

[Craig Robinson]

you know, I've got a job. I work for the coaches association. I'm coaching my kids teams and I'm doing this podcast. I don't have time for just, just, you know, real wives. Real housewives on Real Housewives of Brooklyn. I don't have time.

[Conan O'Brien]

Is there a Brooklyn housewives?

[Craig Robinson]

Yeah, there is.

[Chelsea Clinton]

There is not New York. It's not Brooklyn.

[Craig Robinson]

Oh, well, I bet they all.

[Chelsea Clinton]

This is what I'm dealing with.

[Craig Robinson]

I bet they all live.

[Chelsea Clinton]

No, they don't.

[Conan O'Brien]

Does that. Real housewives, Staten Island. You should check that out.

[Craig Robinson]

Is there really?

[Conan O'Brien]

No, I just made it up.

[Craig Robinson]

Do you have to recuse yourself when.

[Conan O'Brien]

No, because I really have no power in this thing. I'm like the cruise director on the boat. I'm not the captain. I steer it. My job is to get everyone to play a little shuffleboard.

[Craig Robinson]

Yeah.

[Conan O'Brien]

Get em drunk and then, you know, hope that we don't hit anything. But that is my job. So no, I don't have to refuse myself. I'm allowed to be really excited should things work out for Rose. But if not, you know, she still gave an amazing performance.

[Craig Robinson]

Yeah.

[Chelsea Clinton]

Well, it's been great having you.

[Conan O'Brien]

This has been lovely. Again, these things are what's a joy. Honor to talk to you both and likewise.

[Chelsea Clinton]

And it's always a joy. Really, really.

[Conan O'Brien]

It's a really good time.

[Craig Robinson]

It's great to get to know you more and thank you for doing this.

[Conan O'Brien]

So you and I are going to be hanging out a lot now, Craig.

[Craig Robinson]

Anytime you want to hang.

[Conan O'Brien]

I don't think that's true.

[Craig Robinson]

Yeah. Any.

[Conan O'Brien]

I'm going to start cold calling him.

[Chelsea Clinton]

It's true for you.

[Craig Robinson]

So here's the thing. When I come to La Rey gets Conan, when I. Let's hang, let's hang.

[Conan O'Brien]

Let's shoot some hoops.

[Chelsea Clinton]

That's right.

[Conan O'Brien]

I'm going to drain some threes from 80 yards away. They don't go anywhere near the bucket. Nowhere near.

[Chelsea Clinton]

I tell you. That's the baby.

[Craig Robinson]

And then I'll go to the back alley comedy club with you.

[Conan O'Brien]

I think you would do better. You would do better at comedy than I would at basketball. That I promise you. Would you.

[Chelsea Clinton]

Would you teach him how to do ventriloquism? Can he just.

[Conan O'Brien]

I don't do ventriloquism. But I will get a person to teach you ventriloquism. But we have to get you the right dummy, too. It's got to be a good dummy. You could not have teed up our one year anniversary. Oh, my God. No way. Look at this surprise for both of them. Better.

[Chelsea Clinton]

Why don't you do the honors?

[Conan O'Brien]

Do the honors.

[Craig Robinson]

Look at this. Oh, my goodness. You guys are too much. It's a little.

[Conan O'Brien]

Can I just say, do you see? This is beautiful and horrifying at the same time. This dummy has had very bad work done.

[Chelsea Clinton]

Look at his hands. His hands are huge.

[Conan O'Brien]

Yeah. This is the nightmare that will never end for me. I'm probably. I'm gonna be trying to do the Oscars and I'll stop because this face will be looking at me.

[Craig Robinson]

Could you see if we were there in the front row?

[Conan O'Brien]

Put him in the front row. Hey, Conan. We'll put him right next to Timothee

[Craig Robinson]

Chalamet and heckle you.

[Conan O'Brien]

Yeah.

[Craig Robinson]

Yeah.

[Conan O'Brien]

Hey, Conan. Yeah. Having fun up there? Get some better material, Conan. He's gonna steal the show at the Oscars. Yeah.

[Craig Robinson]

Really tall dummy it is.

[Chelsea Clinton]

Well, it should go on your lap.

[Craig Robinson]

It's on my lap.

[Chelsea Clinton]

Oh, okay. Well, he's a basketball player. He's tall. He's a basketball player.

[Craig Robinson]

This is perfect.

[Chelsea Clinton]

Do you ever find yourself scrolling through headlines, especially health headlines, and just thinking that can't be true? Well, I certainly do. 2025 brought us some ridiculous, far fetched health claims and some especially terrifying changes in public health. What's in store for us in 2026? I'm Chelsea Clinton and we're back with season two of my podcast, that Can't Be True. Follow along and catch up on season one wherever you get your podcasts.