Podcast Summary: Conan O’Brien on What Can Go Wrong at the Oscars

The New Yorker Radio Hour
Host: David Remnick
Guest: Conan O’Brien
Date: February 20, 2026

Episode Overview

This episode features a lively and insightful conversation between David Remnick and Conan O’Brien, focusing on Conan’s upcoming second stint as Oscars host, the unique perils and pleasures of live television, the evolution of comedy in a turbulent political climate, and O’Brien’s personal approach to humor, grief, and career reinvention in a changing media landscape. The talk is punctuated with Conan’s signature irony and self-deprecation as he reflects on the art and unpredictability of comedic performance on Hollywood’s biggest night.

Key Discussion Points and Insights

1. The Challenge of Hosting the Oscars

• Hosting as High Risk/Low Reward

  • Remnick notes the thankless nature of the Oscar hosting gig, calling it “a high risk, maybe even low reward gig…endlessly long…a parade of self congratulation and sanctimony” (00:22).
  • Conan, reflecting on last year’s show, jokes: “If you’re still enjoying the show, you have something called Stockholm syndrome. And I guess we all do” (00:54).

• On Preparation & Material

  • Conan likens preparing material to “RAF pilots in 1940. You have to generate a lot of them. A lot of them fall by the wayside, and then some endure” (01:43).
  • He tries out material at comedy clubs: “It’s good to keep you in shape or get you ready. Does it really help? I think it does, but I couldn’t prove it to you having watched the Oscars” (01:55).

• Writers’ Room Process

  • Describes his writing process as reminiscent of Glengarry Glen Ross, “I go down there and they’re all around a long table. And these premises are no good. We gotta get the Glengarry premises. And I yell at them. I’m the Alec Baldwin who comes in, gives that great speech up front” (03:16).

2. Political Comedy at the Oscars

• O’Brien appreciates the tradition but notes, “It’s tricky...I’ve done political comedy over the years...But it’s never been in the front of my comedy brain…I, for better or worse, have a brain that scrambles things, loves cartoon imagery...” (04:08).

• On Trump:

  • “No...if he were a magazine, it’s the National Enquirer...It’s very difficult or I think, impossible to do. And I think Trump, to me, if he were a magazine, it’s the National Enquirer...That’s what the real magazine’s coming out with. You can’t do a comedic take on that” (05:07).

  • “There are comedians who, when they talk about Trump, they quickly get very angry. And I’ve said this before, but I think it’s possible to surrender your best weapon. Your best weapon is to be funny. And if it just evolves into name calling...in the current climate it can be...things have gotten so stretched out...it’s hard to get a grasp on what’s the straight line here” (07:30).

3. Navigating Network Rules & Standards

• Conan analogizes the process to living in a New York co-op:
  • “…everything ultimately is a New York co-op. You know, they have their rules…you can, you can say, hey, but on this other award show, I got to do this right?...‘No, no, no, no, no, we don’t let people alter the windows here at the Drake…and...over at the Macklemore...Yes, we know. That’s the Macklemore.’” (08:34 – 09:51)

4. Handling Mishaps and Unplanned Disasters

• On Oscar fiascos, from streakers to slapping:
  • “No, I’m someone who likes, you know, I don’t want anyone to slap me.” (10:36)
  • Joking: “I’d like a streaker. And you know what? I’d really like a streaker to slap me. That would just satisfy so many of my dormant Catholic hangups” (10:44).
  • He thrives on improvisation: “If accidentally a light falls, you can make a whole show about that...People...instinctively know when something is real and of the moment...that is 10 times the value of anything you could have written” (11:14).

5. Conan's Personal Comedy Ethos

• Claims his on-stage persona and off-stage self are quite similar:

  • “I’m always this guy...I routinely will just talk to people on the street, complete strangers...I think it’s glandular” (12:18).

• Recalls his father’s reaction to his comedic tendencies:

  • “He said...I see, you’re making a living off of something that should probably be treated...You have this. I see your synapses and your...rhythm of your circulatory system...” (12:47).

6. Processing Grief Through Humor

• After the passing of both parents, Conan used comedy as a genuine coping mechanism:

  • Shares a story: “I got this lovely text from Will Arnett...He writes this lovely note, and I just wrote back, I blame Bateman. And then he wrote, oh, I guess we all have our coping mechanisms...and I cut him off and say, Jason Bateman killed my father. Which is insane, but it’s...Make of it what you will. That’s what I said” (13:54).

  • When his mother died days later, Conan kept the same irreverent approach:

    • Conan: “Will texts me...he said, oh, if you want, I could have Bateman take care of your sister. And I immediately texted back, 3053 Beacon street, apartment 17F. Make it look like a robbery” (15:31).
    • His sister’s response: “You don’t think I could take Bateman?” (16:57).

  • “That is how I communicate. You know, that is. I’m a whale. He’s a whale. We make these weird noises at each other. That’s how we communicate” (15:55).

7. Early Formation of Comedic Identity

• O’Brien recounts the process of discovering his comedy “arrow”:

  • “Am I an athlete? No, I am not an athlete. Do the girls go crazy for me? No, they do not. Am I a math whiz? No, Conan, you are not...And it’s a lot of no’s. And then I hit this thing where I would make people laugh in class...The teacher would have me read them and everybody would be laughing. Cause I put a lot of comedy in there. There’s this one arrow in my quiver” (19:26).

• The influence of cartoon comedy:

  • “I never got too analytical about it...just learning about rhythm and what’s funny and why is that funny?...the rhythm of Warner Brothers cartoons, the classics. The rhythm is perfection...” (21:14).

8. The Changing Landscape of Late Night TV and New Media

• O’Brien is pragmatic and unsentimental:

  • “Things are constantly changing. Look at all the things that are changing all the time. And so people are saying, this is tragic...I’ve said this to Stephen...you are doing the best you can, and you’ve done...an amazing job...the larger picture...voices being silenced, they really get silenced. I don’t think that’s gonna happen with, with...Kimmel or Stephen Colbert or anyone who’s doing a late night show” (22:25 – 24:21).

• On Personal Reinvention:

  • “I left my late night show four years ago...I think I reach more people now, either through the podcast or in the travel show...types of interviews I never could have had in that old format...they’re being replaced by a multitude of other ways to connect with people and be funny and be satirical and be probing and let your talent run wild...you can be master of your own destiny. You’re not working for, ultimately, a giant toothpaste company or whoever it is owns your studio” (24:24).

9. Confronting Mortality and Loss in Comedy

• On the death of close friends Rob and Michelle Reiner:

  • “To have that experience, saying good night to somebody and having them leave and then find out the next day that they’re gone...I think I was in shock for quite a while afterwards. That was just...it was. I mean, there’s no other word for it. It’s just very. It’s so awful...” (26:10).

• Tribute to Rob Reiner and Catherine O’Hara:

  • On Rob Reiner: “I think it’s seven movies that Rob Reiner made in quick succession that are classics now...Spinal Tap, when it came out...was like...splitting the atom moment” (27:50).
  • On Catherine O’Hara: “Who’s a funnier performer than Catherine O’Hara? And...she’s possibly the nicest person I’ve ever met, just ever met, just glowed and goodwill” (28:53).

• How loss shapes the present:

  • “You’re always in the process...If you’re lucky you don’t think about it for the first couple of decades of your life. And then it’s people saying, did you hear? And you walk around concussed for a week. So that’s what it is now. I guess I was in a good mood when I got on this podcast” (29:50).

Memorable Quotes by Timestamp

• On Oscars Material:

  • “It’s Hollywood’s biggest night that starts at four in the afternoon. Everyone here just had brunch.” — Conan O’Brien (00:45)

• On Comedy Coping with Tragedy:

  • “Jason Bateman killed my father. Which is insane, but it’s...Make of it what you will. That’s what I said.” — Conan O’Brien (14:45)

  • “Will texts me...‘oh, if you want, I could have Bateman take care of your sister.’ And I immediately texted back, ‘3053 Beacon street, apartment 17F. Make it look like a robbery’...she texted me and said, ‘you don’t think I could take Bateman?’” — Conan O’Brien (15:31, 16:57)

• On Trump & Satire:

  • “If a magazine has as its coverage Elvis, still alive, marries Alien and they have a baby, that’s a three speed blender. That’s what the real magazine’s coming out with. You can’t do a comedic take on that...Trump, to me, if he were a magazine, it’s the National Enquirer.” — Conan O’Brien (05:07)

• On Live TV Mishaps:

  • “If accidentally a light falls, you can make a whole show about that...People instinctively know when something is real and of the moment...that is 10 times the value of anything you could have written.” — Conan O’Brien (11:14)

• On Personal Development:

  • “There’s this one arrow in my quiver. There’s not 35 arrows...I think I started probably working this comedy thing unconsciously in what, 1972, 1973...” — Conan O’Brien (19:54)

• On Changing Media:

  • “They’re being replaced by a multitude of other ways to connect with people and be funny and be satirical and be probing and let your talent run wild that, in some ways, are more freeing and you can be master of your own destiny.” — Conan O’Brien (24:24)

• On Grief and Podcasting:

  • “You walk around concussed for a week. So that’s what it is now. I guess I was in a good mood when I got on this podcast.” — Conan O’Brien (30:23)

• On Remnick’s Interviewing Style:

  • “This is a colonoscopy right now. And there’s been no...Profofol...You used a 1955 Hasenblad. You jammed it up there.” — Conan O’Brien (30:24)

Timestamps for Notable Segments

• Oscar Host Prep and Material Testing: 01:43–02:17
• Handling Network and Academy Rules: 08:09–09:51
• Dealing with Political Satire and Trump: 05:03–07:30
• Coping with Parental Loss through Comedy: 13:54–15:31
• Shift from Late Night to Podcast/Media Reinvention: 22:21–24:24
• Reflecting on the Loss of Friends (Reiners, O’Hara): 25:38–29:50
• Comic Persona Origins: 19:26–21:14

Tone and Style

This episode delivers classic Conan O’Brien: sharp, self-deprecating, and sardonic, but also reflective and capable of candid, unsentimental wisdom about comedy, personal tragedy, and a changing industry. Remnick’s probing, quietly amused questions set up O’Brien’s riffs and heartfelt admissions, creating a conversation that is as thoughtful as it is funny.

Conclusion

“Conan O’Brien on What Can Go Wrong at the Oscars” offers more than backstage anecdotes—it's an examination of the comedian’s mind in the spotlight, in grief, and in an evolving cultural moment. Through humor and honesty, Conan demonstrates how the comedy “arrow” in his quiver has not only sustained him through career shifts and personal losses, but also allowed him to connect, improvise, and thrive in a rapidly changing media world. For anyone interested in the craft of comedy, the evolution of late night, or just in need of a laugh laced with insight, this conversation is essential listening.