Conan O'Brien (Extended) | Oregon Fail

Summary

The Late Show Pod Show with Stephen Colbert

Guest: Conan O'Brien (Extended) — “Oregon Fail”
Release Date: September 30, 2025

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Episode Overview

In this lively and extended episode, Stephen Colbert welcomes legendary late night host and comedian Conan O'Brien. The conversation is a blend of contemporary political satire—with an especially sharp focus on satirizing Donald Trump's latest antics relating to Portland, Oregon—as well as a deep, humorous, and heartfelt discussion covering O'Brien’s latest ventures: his new dramatic film role, the recent Emmy win for "Conan O'Brien Must Go," and personal anecdotes about family, faith, and the peculiar world of late-night television.

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Key Discussion Points & Insights

1. Satire and Commentary: "Waregon," Medbeds, and Trump’s Reality

(01:30 – 12:39)

• Portland/“Waregon” Monologue:
  Colbert lampoons fake war rhetoric, referencing Trump’s imaginary war in Portland:

  “History will never forget the battle of Portland when we freed the citizens from the tyranny of overpriced doughnut shops and white ladies with dreadlocks named Raindrop.”
  — Stephen Colbert, 01:51

  Conan chimes in with a classic quip about Portland:

  “A delicious quiche at the farmer’s market.”
  — Conan O’Brien, 03:22

• Satirizing Trump’s TV Reality:
  Mocking the confusion between Fox News footage and reality:

  “Apparently, Trump thinks everything he sees on TV is real. Next, I'll be sending troops into that building in New York where only murders happen. Martin Short is antifa.”
  — Stephen Colbert, 04:52

• AI, Medbeds & Disinformation:
  Colbert delivers an extended riff on Trump reposting AI disinformation about magical “medbeds”:

  “The President of the United States posted an AI video of a Fox News report that never happened featuring a fake version of himself saying things he never said about a magic foot growing back body pod that does not exist. All reported by an AI anchor of his real daughter-in-law.”
  — Stephen Colbert, 06:29

• Justice Department Satire & Ty Cobb Quip:
  Lampooning the messy indictment of former FBI director James Comey, Colbert jests:

  “It’s never great when you present your case and the judge’s response is the same they’d have if the prosecutor was a golden retriever.”
  — Stephen Colbert, 11:25

  On Ty Cobb’s defense:

  “Ty Cobb knows what he’s talking about. Not only was he Trump’s lawyer, he also used to represent the great and powerful Oz.”
  — Stephen Colbert, 12:13

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2. Conan O'Brien Interview: Late Night Legacy, Dramatic Acting, and Personal Reflections

(14:01 – 37:29)

a. On Saying Goodbye to Late Night

• Conan reflects with wry humor on leaving late night and advising his peers:

  “Remember what I told you? I said, take care of late night. If you take care of late night, late night will take care of you… and whatever you do, don’t speak truth to power… Cowardice is the way.”
  — Conan O’Brien, 14:49–15:16

b. Transition to Dramatic Acting

• Conan discusses his first feature dramatic film, “If I Had Legs, I'd Kick You”:

  “For 28 years, I sat where you sit and I watched other people throw to their movie clips, and a jealousy started to grow. I never got to throw to a movie clip.”
  — Conan O’Brien, 17:17

• In a playful twist, Conan insists on both setting up and introducing his own film clip—a long-held dream after years as a late-night host.

• Scene Description & Role: Conan plays Rose Byrne's exhausted therapist:

  “I'm her therapist. I've been her therapist for a long time. I am tired. I want out of this relationship, this therapist relationship.”
  — Conan O’Brien, 19:26

• Preparation and Acting Experience:

  “I've worked very hard on this and then had my scenes with the insane Rose Byrne, who's so great… I was scared, and I don't like to be scared, but I know it's important still to be scared..”
  — Conan O’Brien, 23:47

c. On Makeup and Character Choices

• The two riff on Conan’s appearance in the film:

  “Why did you want the character to look like an old Dutch woman?”
  — Stephen Colbert, 24:41
  “You know, I'm a beautifully aging older woman from somewhere in the northern climes of Europe.”
  — Conan O’Brien, 25:10

d. Shared Catholic Upbringings & Vatican Anecdotes

• Both reminisce about their Catholic childhoods and jointly visiting the Vatican:

  “He has these Swiss Guards... I’ve seen better in Vegas. All right… They're wearing multicolored incense, and they come in with axes—broad axes!”
  — Conan O’Brien, 26:11-26:32

• Memories of arriving late at church:

  “We would roll up to St. Lawrence’s Church in Brookline, Mass, easily 15 minutes late… My dad would walk down the aisle…And he’d be like this… yeah, come on, come on, come on. And we went. You know, it was a horror show.”
  — Conan O’Brien, 28:01–29:05

e. Parental Pride, Fame, and the Jim Carrey Anecdote

• On his parents’ expectations:

  “When you're third of six, there comes this thing where they're like, he's got a job. And I think if I had called him up and said, I'm a hitman for the mob, but I have my own apartment that have said, good job.”
  — Conan O’Brien, 30:12

• Hilarious story of his mom unwittingly advising Jim Carrey:

  “She said, well, he's interested in comedy. And I told him my son had a struggle, but you stick with it, Stick with it… And I said, mom, when you go to work on Monday, I want you to tell everyone in the office that you told Jim Carrey to stick with it.”
  — Conan O’Brien, 32:55

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3. Recent Success: “Conan O'Brien Must Go” and Austria Adventures

(34:14 – 36:41)

• Conan has just won an Emmy for “Conan O'Brien Must Go.” He talks about shooting in Austria, dressing as Freud and embracing surreal, unscripted moments:

  “My favorite thing is when I get to shoot these parts, there are times where I lose my mind and they just keep rolling the camera… I’m dressed as Freud, Sigmund Freud, in Freud's office, doing the whole makeup… I lay on an air mattress in Sigmund Freud's office… and then I start to free associate.”
  — Conan O’Brien, 34:32–36:03

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Notable Quotes & Memorable Moments

• On Late Night Wisdom:

  “Take care of late night. If you take care of late night, late night will take care of you.”
  — Conan O’Brien, 14:49

• On Acting Nerves:

  “I was scared, and I don't like to be scared, but I know it's important still to be scared, even at my advanced age.”
  — Conan O’Brien, 23:53

• On Parental Success:

  “If I had called him up and said, I'm a hitman for the mob, but I have my own apartment, they'd have said, good job.”
  — Conan O’Brien, 30:12

• On Relatability:

  “We're both doing jobs where we do things that we would do if no one was paying us... It’s just chicanery and foolishness we're doing.”
  — Conan O’Brien, 34:45

• Heartfelt Goodbye:

  “The connection you have with your audience, you're taking with you. No one else owns that. That's yours.”
  — Conan O’Brien, 15:40

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Timed Key Segments

• Political Satire: “Waregon” War & Medbeds – 01:30–12:39
• Conan on Late Night & Advice to Hosts – 14:01–16:29
• Conan’s Film Debut & Host-Guest Roleplay – 16:44–21:23
• Anecdotes on Acting, Makeup, and the Vatican – 23:43–27:11
• Catholic Childhood & Arriving Late at Mass – 27:11–29:26
• Parental Pride & Jim Carrey Story – 30:03–33:51
• Austria, “Conan O'Brien Must Go”, Emmy Win – 34:14–36:41

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Episode Tone

The conversation is playful, sharply satirical, and frequently self-deprecating, blending the absurdities of American politics with warm, personal anecdotes and classic late-night camaraderie. O’Brien and Colbert’s rapport is marked by mutual respect, irreverent humor, and an underlying note of poignancy as they reflect on family, legacy, and the enduring appeal of authentic connection in comedy.

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For New Listeners

This episode is a must-listen for fans of political satire, late-night television, and comedy history, offering plenty of laughs and genuine insights into the creative minds of two late-night legends. Conan’s personal stories and behind-the-scenes reflections, in particular, add depth and heart to what is otherwise a riotously funny episode.

Transcript

[Stephen Colbert]

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[Conan O'Brien]

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[Stephen Colbert]

Welcome, welcome one and all in here out there. Welcome everybody to the Late Show. I'm your host Stephen Colbert. My fellow Americans, I come to you tonight with the sobering news that our nation is at war. It's Waregon. How did we arrive at this dark day? I don't know, but when was this Saturday? Saturday morning Donald Trump posted. I am directing Secretary of War Pete Hegseth to provide all necessary troops to protect war ravaged Portland. Yes, history will never forget the battle of Portland when we freed the citizens from the tyranny of overpriced doughnut shops and white ladies with dreadlocks named Raindrop. Wow. Thank you. Thank you very much. Make it some really my hair out into a cake. Of course, this isn't our first war with Portland. We've all seen the classic war movies like Full Flannel Jacket and all vegan on the west side brunch, Portland residents were surprised to find themselves at war with their country. And to undercut Trump's claims, they posted images like this beautiful park and this open air bakery stand that does not prove that they are not at war. However, remember the stirring Vietnam protest song, what is it good for?

[Conan O'Brien]

A delicious quiche at the farmer's market.

[Stephen Colbert]

Oh, the pipes. It's the pipes, man. They grab you. You know what I mean? Right there.

[Conan O'Brien]

Hit it right there.

[Stephen Colbert]

One of the justifications, one of the justifications Trump has continually used for sending troops into our own cities is to protect ICE facilities. And there was a protest outside a Portland ICE building the day that he announced. In fact, for most of the day, the only protester was one man in a chicken costume. It's chaos. There are reports that the chicken crossed the road several times and authorities are still asking why. So what the cluck is going on? One extremely credible theory is that Trump watched a single Fox News report earlier this month which mixed current video of smaller anti ass protests with video of much larger protests back in 2020. Supporting this theory is that when Trump spoke to Oregon's governor Tina Kotek this weekend, she told him there was no rioting and no need for troops. To which he said, well, wait a minute, am I watching things on television that are different than what's happening? Yes.

[Conan O'Brien]

Yes, we.

[Stephen Colbert]

Good guy, y'.

[Conan O'Brien]

All.

[Stephen Colbert]

Hey, thanks. Apparently, Trump thinks everything he sees on TV is real. Next, I'll be sending troops into that building in New York where only murders happen. Martin Short is antifa the president. He isn't just falling for fear mongering Fox News stories. He's also falling for the most cuckoo banana pants health flim flam on the entire Internet. This weekend he posted an AI video about a fake cure all device called Medbeds, which according to far right conspiracy theories are futuristic medical pods that can cure any disease and even regrow limbs and which supposedly the American government has access to. Well, we all know that's not true. If the government had the power to regrow limbs, Trump's hand wouldn't look like a banana. You forgot in your backpack. Of course. Say it again. Hey, say it again. Of course. Since it's a right wing conspiracy, they're saying that these miraculous med beds are something liberals have been hiding from the American public. Busted. It's true. I have a med bed. I'm actually 153 years old. If I slept in a normal bed at night, the show would look like this.

[Conan O'Brien]

We've got a great show for you tonight. Conan o' Brien is here. I'm going to ax him a question.

[Stephen Colbert]

To be clear, I have a great makeup team. To be clear, the starting point for this post, the part that Is least bizarre is the magical medical beds. Okay? That's the base code. That subject is just the plain which we're about to pour the crazy sauce cuz it gets way weirder. Here's the AI video featuring fake Lara Trump that the president posted. Breaking now, President Donald J. Trump has announced a historic new health care system, the launch of America's first med bed hospitals and a national medbed card for every citizen. Every American will soon receive their own medbed card. With it, you'll have guaranteed access to our new hospitals led by the top doctors in the nation. What in the ever lovin angel dusted Huff rag is that? The President. Stay with me here. The President of the United States posted an AI video of a Fox News report that never happened featuring a fake version of himself saying things he never said about a magic foot growing back body pod that does not exist. All reported by an AI anchor of his real daughter in law. After watching that, I hope they have med beds so I can regrow my brain back. Do you understand? Do you understand how crazy that is? Is this working? It really helps. It really. It really seems like Trump saw the AI video of himself and thought it was real. Which means he also thinks in 2020 he did this. The best. I tell you, it was the best debate we had. He said build back bongo. And then I was a snake charmed by his ancient rhythm. Now, Trump rarely takes down any posts, no matter how crazy they are. But in this case, Trump later deleted the video after it was up for about 12 hours. I wonder which staffer drew the short straw. Oh, that one. Mr. President, I see you posted about med beds. Is that the word I see you posted about the med beds. What say we take that down and we put that in your special top secret file along with your idea for a hamburger woman hybrid that can't get pregnant. Okay, special sauce. So Trump sending troops to a major US City and simultaneously losing all touch with reality. But you know what? Things could be worse. And they are. Because Trump is also destroying the Justice Department. Because. Fun story. On Thursday night, bowing to pressure from the President, former FBI Director James Comey was indicted on two charges. That is chilling. If Trump. Yeah, chilling. If Trump can indict a former FBI director. Anyone who has ever stood up to Trump has to worry about being thrown in jail. And I will fight that with every fiber of my being or my name is not Jimmy Fallon. F A L L O N Come at me, bro.

[Conan O'Brien]

No, it ends here.

[Stephen Colbert]

Where's my time? Keep in mind this comes after Trump singled out several enemies in a public message to Pam Bondi posting what about Comey? Adam Schifty, Schiff, Latisha, they're all guilty as hell. The U.S. attorney who was originally assigned to the Comey case refused to indict because the investigation evidently didn't turn off enough evidence. So Trump fired him and pressured Bondi to appoint new U.S. attorney and Maybelline Terminator Lindsey Halligan. This appointment of Halligan, who has never prosecuted one case ever, that the internal Justice Department email announcing Halligan's arrival misspelled her first name. That wasn't even the worst misspelling. The document came in letterhead that said US Justin's depoopment. Depoopment. Yes, Peabody, please. So far Halligan is not doing good cuz the grand jury voted to indict Comey on only two of the three counts that Halligan originally sought. So she drew up a second list of indictments that only included the two that they did indict him on. But somehow both of those documents were filed with the court, which meant that two versions were published on the docket case, to which the judge said so this has never happened before. It's never great when you present your case and the judge's response is the same they'd have if the prosecutor was a golden retriever. Now, ladies and gentlemen, I'm no lawyer, but you know who is Trump's former defense attorney, Ty Cobb. And he doesn't think this case has much of a chance. I don't see any way in the world that Comey would be convicted. And I think there's a good chance because of, you know, the wholly unconstitutional authoritarian way that this was done, that the case may get tossed out well before trial. And Ty Cobb knows what he's talking about. Not only was he Trump's lawyer, he also used to represent the great and powerful Oz. We got a great show for you tonight coming up.

[Conan O'Brien]

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[Stephen Colbert]

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[Conan O'Brien]

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[Stephen Colbert]

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[Conan O'Brien]

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[Stephen Colbert]

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[Conan O'Brien]

Ooh.

[Stephen Colbert]

Folks, my guest tonight is a promising actor making his feature film debut in if I Had Legs, I'd Kick you. Please welcome back to THE Late Show, Conan o'. Brien.

[Conan O'Brien]

How you doing? Very nice.

[Stephen Colbert]

Hey, nice to see you again. Nice to see you.

[Conan O'Brien]

Thank you so much. Thank you.

[Stephen Colbert]

Yeah.

[Conan O'Brien]

Stephen, how's late night? What's going on? I've been out of it for a little bit. Catch me up on what's happening. Okay.

[Stephen Colbert]

I'll send you the obituary now. You've been out for four years. Four years. Four years. So what do you.

[Conan O'Brien]

I remember just as I was leaving my late night show, I took you and all the other late night hosts out. Do you remember this?

[Stephen Colbert]

Yes.

[Conan O'Brien]

I took you to a wonderful Sizzler restaurant and we all had our trays and I told you guys. Remember what I told you? I said, take care of late night. If you take care of late night, late night will take care of you.

[Stephen Colbert]

Remember you did say that. Yeah.

[Conan O'Brien]

I said, don't do anything to ruffle any feathers. Remember I said that?

[Stephen Colbert]

Yes. You shook your shillelagh.

[Conan O'Brien]

I had a shillelagh. It was actually a piece of steak. I was shaking at you.

[Stephen Colbert]

It was the shank of the bone.

[Conan O'Brien]

Yes, exactly. And I said. I said, and whatever you do, don't speak truth to power.

[Stephen Colbert]

Yes.

[Conan O'Brien]

I said. Cowardice is the way.

[Stephen Colbert]

Yes.

[Conan O'Brien]

In 28 years of my show, I never read the news. I had a masturbating bear and a plastic dog. I didn't even know who was president. I.

[Stephen Colbert]

Thanks for being here, Conan. You. I am lovely man.

[Conan O'Brien]

I, of course, adore you. I love you. I know you as a person and also as a comedic force. And I have very, like a lot of people, I'm very sad that this chapter is ending. But I also want to say that you are going to do amazing things. You're going to have a lot of fun and the connection you have. And this isn't just you. It's Mr. Kimmel and Fallon. All these guys have. It will. It's very special, the connection you have with your audience. You're taking with you. No one else owns that. That's yours. That's yours. Well, you would know for the rest of your life.

[Stephen Colbert]

Well, you would know, because your audience owns a lot of you.

[Conan O'Brien]

That's right.

[Stephen Colbert]

Lovely people, you know.

[Conan O'Brien]

Very nice meeting. True story.

[Stephen Colbert]

Thank you.

[Conan O'Brien]

Good man.

[Stephen Colbert]

Thank you. Now, let's get to the heat of the meat here, Conan. All right. I know you've been trying to avoid the. You've been. You've been avoiding these questions. You've been a late night host, a live performer, a podcast, a travel show host, a storied comedy writer, Saturday Night Live, the Simpsons. Now you add to your resume dramatic actor.

[Conan O'Brien]

Yes.

[Stephen Colbert]

Is that possibly real?

[Conan O'Brien]

Yeah.

[Stephen Colbert]

Because when my producer told me, I did not believe them.

[Conan O'Brien]

Yeah. Yeah. So I have to say this is all real. And I am in a movie. And it happens to be an excellent movie. It's a very, very good movie.

[Stephen Colbert]

If I had legs, I'd kick you.

[Conan O'Brien]

If I had legs, I'd kick you. Directed and written by Mary Bronstein, incredibly talented filmmaker and starring Rose Byrne, who is wonderful actress, absolutely insanely phenomenal. And when I was offered this part, I immediately said yes. And for one reason. For 28 years, I sat where you sit and I watched other people throw to their movie clips, and a jealousy started to grow. I never got to throw to a movie clip. I just didn't ever get the chance.

[Stephen Colbert]

Well, we have a clip. Do you wanna.

[Conan O'Brien]

I would so love. No, no, you don't understand. 28 years I watched some of the greatest statues in the world. And then I would say. They would do the big setup, and then I would sit where you are and say, let's take a look. Okay. Tonight I want to do both. I want to set up my clip, and if you are amenable, we'll quickly switch seats. Not yet. Not yet. I'll set up the clip here, and then I'll run over there. And then I want to do the host part, if it's okay. It's never been done before. And as we.

[Stephen Colbert]

So you're gonna say, let's see the clip.

[Conan O'Brien]

No, no. I'm gonna describe the scene, turn to the host.

[Stephen Colbert]

Oh, I see.

[Conan O'Brien]

Then I run over and I say, let's take a look.

[Stephen Colbert]

Cause I do that.

[Conan O'Brien]

I do that better than any host.

[Stephen Colbert]

But can I. But I. Can I ask you to do the hardest part?

[Conan O'Brien]

Yes.

[Stephen Colbert]

Which is after the clip is over. Have a reaction to the guest's clip.

[Conan O'Brien]

Yes. Do you want me to do that?

[Stephen Colbert]

It has to both be positive and not reveal that you haven't seen the movie.

[Conan O'Brien]

Yes. I can do that, too.

[Stephen Colbert]

Okay, great.

[Conan O'Brien]

You ready for this?

[Stephen Colbert]

You ready?

[Conan O'Brien]

I'm gonna do it fast. Okay. I Got offered this role and let me explain the part really quickly. Do you need to set this up, Rose Burns? Yes, I'll set it up. Thank you. I'll set up the clip.

[Stephen Colbert]

Yeah.

[Conan O'Brien]

Oh, and by the way, we brought a clip.

[Stephen Colbert]

Oh, wow, that's great.

[Conan O'Brien]

Yeah. And for years.

[Stephen Colbert]

Do you need to set this up?

[Conan O'Brien]

For years I watched actors get all pushy in Taipei and go, do they have the clip? Do they have it? Do they have it? And then you say, yes, we have the clip.

[Stephen Colbert]

We have the clip.

[Conan O'Brien]

Yeah.

[Stephen Colbert]

And say, okay, but you know what I really love? What is when you say, we have a clip here, what's this? And the actor would go, I don't know. Yeah, that's also fun.

[Conan O'Brien]

Here's what you need to know for this clip. And it's not long. I am Rose Byrne's character's therapist. She is at the end of her rope. She is really. I mean, her performance is stunning and she is at the very end of her rope. I'm her therapist. I've been her therapist for a long time. I am tired. I want out of this relationship, this therapist relationship. I think that's the best way to describe it. This is one of the scenes where you see that, you know, you're starting to smell burned rubber here with the therapist and he wants out. And so that's all you really need to know for the cl. Wow. Let's take a look. We do have to stop now. We are out of time. I have another patient coming. So wait, now what about the 10 minute warning? Yeah, I just wasn't paying attention. You didn't respond to the email that I sent you about my dream. I don't respond to my client's dream emails.

[Stephen Colbert]

Okay, so if you don't bring it up, then what is the point?

[Conan O'Brien]

Okay, you got me. I had a dream and I need to talk about it today.

[Stephen Colbert]

And I didn't get any time because.

[Conan O'Brien]

You didn't give me a warning. We can discuss the dream. You emailed the next session. Well, it's actually a different dream. Well, I don't really about you. Okay, quickly stop.

[Stephen Colbert]

Were you surprised you had that extra gear?

[Conan O'Brien]

I mean, I'm surprised I had any gear at all after. How did this.

[Stephen Colbert]

How did this come about?

[Conan O'Brien]

I was.

[Stephen Colbert]

Drama.

[Conan O'Brien]

Well, I was minding my own business and my phone rings and it's a very familiar voice. This is about three years ago. Adam Sandler.

[Stephen Colbert]

And Sandler gets everybody jobs.

[Conan O'Brien]

He gets everybody jobs and he called me.

[Stephen Colbert]

Can you put in a word for me? Because I'm Free in June.

[Conan O'Brien]

Now? I don't think so. But he said, hey, buddy, there's a script. And there's this amazing writer, director Mary Bronstein and the Safdie, one of the Safdie brothers is producing this A24. They want to send it to you and can I give them your number so you can read it? And I said, yeah. And he's like, that's right, buddy.

[Stephen Colbert]

We have to take a quick break.

[Conan O'Brien]

Yeah, I think we should.

[Stephen Colbert]

We'll be right back with more Conan o', Brien, everybody.

[Conan O'Brien]

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[Stephen Colbert]

Back with the one, the only dramatic actor, Conan o'.

[Conan O'Brien]

Brien.

[Stephen Colbert]

Conan, were you prepared? Like, were you off book?

[Conan O'Brien]

Oh, yeah. I've worked very hard on this and then had my scenes with the insane Rose Byrne, who's so great. And I knew I'm in a very small room with one of our best actors, and this has to be good. I was scared, and I don't like to be scared, but I know it's important still to be scared, even at my advanced age. And when they. I learned it backwards and forwards. I worked with Mary Bronstein a lot, and I worked very hard, and she helped me a lot to figure out who this guy is. And then we. When they. When I heard action the first day, my heart was pounding through my chest because I took it that seriously. But people seem pleased, so I'll go with it.

[Stephen Colbert]

And I gotta say, I mean, I love the choice you made this makeup. Why. Why did you want the character to look like an old Dutch woman? I'm just curious. Or are we not Allowed to make jokes about this?

[Conan O'Brien]

No. You. How dare you make fun of me. It is, you know, it's the look I have. You know what?

[Stephen Colbert]

Go with what?

[Conan O'Brien]

You know, I'm a beautifully aging older woman from somewhere in the northern climes of Europe. Yeah, we.

[Stephen Colbert]

Occasionally. It's nice enough that you and I do some social things together. You and me and our lovely wives go out and have, like, dinner or coffee or something like that. Go to the Vatican sometimes.

[Conan O'Brien]

Yeah, we went to the Vatican.

[Stephen Colbert]

You and I went to the Vatican together last summer. Here you are meeting Francis right there.

[Conan O'Brien]

Yeah.

[Stephen Colbert]

What'd you think? I'm just curious. I'm dying to know. Yeah, I'm dying to know if they're applauding you or the Pope. What did you think of the whole thing?

[Conan O'Brien]

It was popular. Oh, what did I think of it? I was just overwhelmed by the pageantry of it. I mean, I know that we both grew up in very Catholic religious situations, and so there's that element of it. And then I was just. He has these Swiss Guards that are.

[Stephen Colbert]

Dressed in the Apostolic Palace.

[Conan O'Brien]

Whatever. Okay. I've seen better in Vegas. All right.

[Stephen Colbert]

And looser slots.

[Conan O'Brien]

Yeah. Yeah. Oh, yeah. I've been to this sphere. No. They're wearing multicolored incense, and they come in with axes. Broad axes. I guess you know them. Real names.

[Stephen Colbert]

Halberd.

[Conan O'Brien]

Ah.

[Stephen Colbert]

They're wearing these sort of pantaloon things that were designed by Michelangelo.

[Conan O'Brien]

Yes. And the one thing he got wrong. They're very garish.

[Stephen Colbert]

Yes.

[Conan O'Brien]

And I just. The whole pageantry of them marching in to protect the Pope with things that look like you're there to slice. I don't know. I mean, wood.

[Stephen Colbert]

Large sausage.

[Conan O'Brien]

Large sausage.

[Stephen Colbert]

Yeah.

[Conan O'Brien]

So I was blown away by all that, but I just kept channeling my parents, who would have just absolutely lost their minds if they knew. And I'm sure it's the same thing for you. You're thinking about all the people.

[Stephen Colbert]

Yeah. My sister came with me and wore my mother's veil to cover her hair.

[Conan O'Brien]

Unbelievable.

[Stephen Colbert]

Yeah.

[Conan O'Brien]

Unbelievable.

[Stephen Colbert]

It was incredible. Yeah. Going to Mass. Six kids in the family.

[Conan O'Brien]

Yeah. There were six of us. We were always late to Mass. The o' Briens were late to everything. We would all pile into this terrible 1978 olds. It was all kind of smashed up, and my father hired a house painter to paint over it. So it had.

[Stephen Colbert]

Painted over.

[Conan O'Brien]

Yeah.

[Stephen Colbert]

Car.

[Conan O'Brien]

Yeah. Yeah. He said, oh, I saw this wonderful young man standing on the median strip, and he said, I'll paint that car. And. Well, he has house Paint. And he had a brush, but, you know, it's the same and it's not the same.

[Stephen Colbert]

Did he paint it on the median strip?

[Conan O'Brien]

I think he did, yeah.

[Stephen Colbert]

Did he do the shutters of the car?

[Conan O'Brien]

It's inside. He put gutters on the car.

[Stephen Colbert]

Oh, my God.

[Conan O'Brien]

We would roll up to St. Lawrence's Church in Brookline, Mass, easily 15 minutes late. No. And then don't woo for no reason.

[Stephen Colbert]

Maybe they're fans of St. Lawrence.

[Conan O'Brien]

I checked the line beforehand. So they roll up. We would roll up at least 10, 15 minutes late. And the thing you do, as you know, if you're running at all late, is you come in the back and you pin your wall to the back and you don't make a sound. And you stand for the whole service. Not my dad. My dad. Not believer in that. My dad would walk down the aisle. He'd get all the way almost to the front while the priest was, you know, speaking. And he would stand in the front, and then he'd turn to all of us. That'll be my camera right there. And he'd be like this. He'd be right here. Yeah, I'll go direct this one. He'd go like, yeah, come on, come on, come on. And we went. You know, it was a horror show.

[Stephen Colbert]

And you're all like seven feet tall, too, so there was no hiding you.

[Conan O'Brien]

Yeah. And it was awful. And it was. And we would shamble down there, shoes squeaking.

[Stephen Colbert]

Yes.

[Conan O'Brien]

We wore tin shoes for some reason. Everything clanging and clattering and it was so. I have a lot of traumatic associations with them. With that. Yeah.

[Stephen Colbert]

Shut up. We'll be right back with more Conan o', Brien, everybody. Hey, everybody. We're back with the one and only Conan o'. Brien. Well, you sadly lost both your parents a year ago, and your mother was a lawyer and your father was an epidemiologist.

[Conan O'Brien]

Yes. Yeah. Very smart.

[Stephen Colbert]

Very smart. You know, Very, very. Did they think that you should have used your intellect for something more valuable to society?

[Conan O'Brien]

Be very careful.

[Stephen Colbert]

I'm just curious. Did they think you should have done something, perhaps a more standard use of the brain power than whatever it is you've decided you did?

[Conan O'Brien]

When you are. When you're third of six, there comes this thing where they're like, he's got a job. And I think if I had called him up and said, I'm a hitman for the mob, but I have my own apartment that have said, good job. They were thrilled that I got work quickly. And they were always fans of What I was up to and the greatest gift I had was getting to introduce my parents to famous people that. I mean, I got to introduce them to presidents and they got to meet all these just amazing people that just. They were stunned. They got to bask in some of that, which really made me happy.

[Stephen Colbert]

Were these celebs nice to your folks? Were they.

[Conan O'Brien]

Everybody was nice. And then we had a really fun experience where I was having a. I lived here doing the late night show late 90s, and I was living on, I think 79th and Amsterdam in a rental. And I had a party and halfway through the party and my mom was in town, so she was at the party too. And it was my staff and we're all hanging out and having a good time. I get a call on my phone, first cell phone ever. And it's Jimmy Miller, who's the manager for Jim Carrey. Jim Carrey at the time had just come off of 4 insane. It was that mania. Yeah, he was the most famous person.

[Stephen Colbert]

Four number one movies, like in one year.

[Conan O'Brien]

In one year. And he said, hey, Conan, I'm in town with Jim Carrey. Can we stop by the party? We hear you're having a party. Can we stop by? This was not a Hollywood. This was just my. I said, yeah, sure, yeah, okay. So lo and behold, Jimmy Miller. And he shows up and there's Jim Carrey, who I'd met like once briefly. But he comes in, he's like, hey, Conan, couldn't be nicer. Everyone in my staff's eyeballs, they're just melting. Like, this is not a guy who would ever have been on our show. At that time. We were still struggling to make it biggest star in the world. And everybody's freaking out. And at one point, I notice my mom is in the corner talking to Jim Carrey, and she's talking to him for a while. And you have that feeling that we've all had where you're like, she detaches. She comes over to me and my mom, I always thought of as Margaret Dumont in the old Marx Brothers movies. Well, Groucho, you know, my mom had kind of a regal air about her. And she said, well. And I said, mom, what were you talking to that guy about? And she said, well, he's interested in comedy. And I told him my son had a struggle, but you stick with it, Stick with it.

[Stephen Colbert]

God bless her.

[Conan O'Brien]

And he's finding his way and you'll find your way. And I said, this is like a Saturday. My mother has to go back to work at Ropes And Gray Law Firm in Boston, State street, whatever, has to go back to Ropes and Gray Law Firm on Monday. And I said, mom, when you go to work on Monday, I want you to tell everyone in the office that you told Jim Carrey to stick with it. Stick with it. And she said, why? Why? Who is he? Why? Why? Why are you doing it? Cause she. She was like, I was always. And I said, just do that. I get a call Monday morning. I hear her. She. I pick up the phone. My mom's on the phone. In the background, I hear 30 people laughing as hard as you've ever heard anybody laugh. And she said, well, I didn't know.

[Stephen Colbert]

Fantastic. We're going to take another quick little break here, but stick around. You know him, we love him. He's a national treasure. Mr. Conan O'. Brien. Conan.

[Conan O'Brien]

Yes.

[Stephen Colbert]

So everybody loves your show. Conan O' Brien must go just won the. The Emmy. Congratulations.

[Conan O'Brien]

Thank you very much. And congratulations to you.

[Stephen Colbert]

Thank you very much. It was a lovely night. Love the night.

[Conan O'Brien]

Great for everybod.

[Stephen Colbert]

The latest episode of Conan Brown Must Go was in Austria. Quality country. I love Vienna.

[Conan O'Brien]

Lovely.

[Stephen Colbert]

What were your favorite parts?

[Conan O'Brien]

My favorite parts were. I mean, first of all, there's so many great. Getting to be on the mountain where Julie Andrews sings the opening for Sound of Music. And I'm in later. Hose and shorts.

[Stephen Colbert]

We've got it. That's it.

[Conan O'Brien]

And yeah, yeah, that was. You know, that's fantastic. You know what's great? And Steven, you will agree with us, we're both doing jobs where we do things that we would do if no one was paying us.

[Stephen Colbert]

Yes.

[Conan O'Brien]

It's just chicanery and foolishness we're doing. And so that was a joy. Everything was a joy on that. But my favorite thing is when I get to shoot these parts, there are times where I lose my mind and they just keep rolling the camera. And those are my favorite. In 30 years of almost 30 years of late night. That was always my favorite thing is my mind snaps and the cameras are rolling and then it goes out into the ether. So I'm dressed as Freud, Sigmund Freud, in Freud's office, doing the whole makeup. And at one point, I do a remote there. And then I lay down on an air mattress on his couch, the famous couch. His couch is not there. It's in London.

[Stephen Colbert]

Okay.

[Conan O'Brien]

And I wanted to lay on his couch, and I find out, no, his couch isn't here. So we ran out and got an air mattress. We inflated an air mattress in Sigmund Freud's office. I lay on it dressed as Freud, and then I start to free associate. And as usually happens, I very quickly turn on my staff as Sigmund Freud having therapy and free associating on an air mattress in Vienna.

[Stephen Colbert]

Now, I understand there's a.

[Conan O'Brien]

Let's take a look. They push me and push me, and Jeff Ross is in the background chewing gum and saying, it looks pretty good. And he shrugs and says, I don't know.

[Stephen Colbert]

I don't eat bread these days. I'm like, well, what the. So you don't eat bread?

[Conan O'Brien]

Is that something we're gonna talk about now? We're gonna die soon, and we're talking about not eating bread. And the writers, they don't care. You know, I just say, that comes.

[Stephen Colbert]

Out of my head.

[Conan O'Brien]

And then written by those guys. Oh, wow, that sounds great. Emmys for everybody. Dr. Freuds. I'm sorry, I think your session is over. That went on and on. We made it to a completely different. Anyway, the film if I had legs, I'd kick you with Rose Byrne is in select theaters October 10th and nationwide October 24th. CONAN O'. BRIEN.

[Stephen Colbert]

Is there anybody better?

[Conan O'Brien]

I don't think so. Oh, it doesn't say that. Okay, we'll be right back with a performance from Broadway's Ragtime Conan o', Brien, everybody.

[Stephen Colbert]

Thank you for listening to the Late show pod show with Stephen Colbert. Just one more thing. If you want to see more of me, come to The Late Show YouTube channel for more clips and exclusives.

[Conan O'Brien]

Tulsa is my home now. Academy award nominee Sylvester Stallone stars in.

[Stephen Colbert]

The Paramount original series, Tulsa King.

[Conan O'Brien]

This distillery is a very interesting business.

[Stephen Colbert]

And we got to know the enemy from Taylor Sheridan, co creator of Landman. What are you saying?

[Conan O'Brien]

I'm all right.

[Stephen Colbert]

If you think you're gonna take me out, it's gonna be really difficult.

[Conan O'Brien]

Tulsa King, New season. Now streaming exclusively on Paramount plus.

[Stephen Colbert]

Now streaming on Paramount plus.

[Conan O'Brien]

It's murphing time.

[Stephen Colbert]

Hefty, can you even lift, bro?

[Conan O'Brien]

Grouchy, I hate the radio. Quiet. Something important to do.

[Stephen Colbert]

I have no idea what he just said.

[Conan O'Brien]

And Smurfette. That's how it's done, boys. Smurfs with a pg.

[Stephen Colbert]

Now streaming on Paramount plus.