The Late Show Pod Show with Stephen Colbert

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

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.

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

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

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

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

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

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.

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.