Conan O’Brien Needs a Friend
Episode: Judd Apatow Returns (October 27, 2025)
Episode Overview
This episode brings back acclaimed director, writer, and producer Judd Apatow for a candid—and frequently hilarious—conversation with Conan, Sona Movsesian, and Matt Gourley. They explore Judd’s new book, Comedy Nerd, swap stories about comedy nerddom, creative anxieties, nostalgia, aging in comedy, and the art and pitfalls of improvisational filmmaking. Plus, there’s a sidesplitting segment with Team Coco’s legal counsel, David Melmed, role-playing music copyright scenarios. The episode is a rich, sprawling blend of industry insight, personal reflections, and unrepressed improvised comedy.
Key Discussion Points & Insights
1. Comedy for All Ages?
[02:22–05:14]
- Matt shares that a friend's nine-year-old listens to the podcast, surprising Conan.
- The team jokes about their surprisingly young (and old) listeners, imagining in-utero podcast fans.
- Matt claims the show has an underlying innocence that makes it somewhat appropriate, prompting Conan to reflect:
“You can listen to it on this very friendly crime fighting level. And then there’s all the nuances that we pack in here.” — Conan [04:15]
2. Dynamic Ad Insertion & Podcast Tech Talk
[04:43–08:12]
- The crew riffs endlessly on “dynamic ad insertion,” with Conan ludicrously asserting he invented it:
“I had an idea about two and a half years ago that ads could be inserted dynamically.” — Conan [05:26]
- Judd and the team play along:
“We were the first to do it.” — Judd [06:23]
- The conversation devolves into comedic wordplay on “dynamic” and “insertion,” eventually remarking on how such suggestiveness might lose their young listeners.
“You were kind of sexualizing it too, a little bit.” — Sona [08:21]
3. Nostalgia, Aging & The Comedy Life
[12:13–18:53]
- Discussion shifts to Judd’s book Comedy Nerd and his hoarder-like archive of comedy memorabilia.
- Judd reflects on nostalgia and workaholism:
“I also finished it and thought it’s so long that it feels like a textbook about workaholism.” — Judd [14:37]
- Conan admits he’s sentimental but tries to “stay in it now,” recalling early career memories with affection.
- Wry observations on being middle-aged in showbiz:
“Just by being older, you’re creepy. You know, if I just go into a dance club and do nothing but stand there...people will call the police.” — Judd [16:54]
“It’s the less you do that’s creepy.” — Matt [17:21] - They each reckon with the surreal prestige their peer group now has, joking about awards and their “illegitimacy.”
4. The Influence of Mel Brooks
[18:53–23:54]
- Both recount their lifelong admiration for Mel Brooks.
- Judd discusses his emotional, in-depth documentary about Mel, noting Mel’s special capacity for emotional candor in old age.
- Conan highlights Mel Brooks’ real-life credentials for mocking Hitler:
“Mel Brooks fought Hitler for real. We talk about any comedian…who fought Hitler. They’re writing from a checkbook that I could never match.” — Conan [20:40]
5. Comedy Nerd Origins & Celebrity Encounters
[38:18–41:53]
- Judd details his comedy-obsessed childhood, including a family connection to comedian Toni Fields.
- Apatow recounts being mesmerized by her ability to be funny about adversity:
“She’s the coolest person in the world...people are adoring her.” — Judd [41:03]
6. Changing Landscape of Comedy
[41:53–43:56]
- The hosts muse on the explosion of comedy (from TikTok to YouTube) and the challenge for filmmakers to keep pace with viral, accidental humor:
“If you’ve got that many people out there, one of them is going to beat any professional comic mind…” — Conan [43:24]
- Judd admits, “Jackass is the funniest thing,” underscoring the baseline appeal of sheer realism and pain in modern comedy.
7. Judd Apatow’s Creative Path & Directing Anxieties
[27:50–35:24]
- Judd shares how a failed audition for Jim Henson (Kermit telling him he “lacked warmth”) helped him pivot away from performing toward writing/directing.
“It’s like Kermit telling you to f*** off.” — Judd [28:52]
- He describes his deep fears about directing, especially concerning technical skills (like eyelines), and how Garry Shandling basically forced him to direct for The Larry Sanders Show, increasing his confidence.
- Judd details his process directing The 40-Year-Old Virgin—heavy improvisation, enormous film stock, much to the crew’s chagrin.
“I just shot so much footage…The crew hated me. The DP, when he saw the finished movie, just said…‘Oh, now I see what you were doing.’ But they really did look annoyed.” — Judd [33:33]
8. Pitfalls of Improv & Authenticity in Film Comedy
[35:24–38:18]
- Conan and Judd note how improv works only when played with deep character commitment. If actors “think they’re being funny,” it destroys the scene.
“Because if you can tell an actor thinks they’re being funny, it instantly is awful.” — Judd [34:50]
- Referencing Pink Panther movies, they amplify the point that laughter should remain in the audience, not on screen.
9. The Joy & Trauma of Growing Up Comedy Nerd
[44:35–49:05]
- The two recount stories of understanding sex, books left by parents on the coffee table, and unintended trauma:
“My parents didn’t have the instinct to go, ‘I think he wants to know the facts of life.’ They’re pursuing the wrong avenue.” — Conan [47:54]
- Judd recalls stoically refusing to admit he stole a sex-ed book, proud that his “tenacity” led to never being spanked again.
10. Collaboration & Building Comedy Community
[51:47–54:05]
- Judd moves into discussing his unique collaborative approach—especially in Knocked Up and Freaks and Geeks—and his pride in seeing past collaborators thrive.
- On working with Norm Macdonald, Conan observes Norm’s indifference to audience response, a “nerve” that was both inspiring and terrifying.
“Norm doesn’t care in a way that frightens me.” — Andy via Conan [53:17]
11. The Infamous Music Rights Q&A with Team Coco’s Lawyer
[58:26–68:38]
- Conan, Judd, Sona, and Matt invite Team Coco lawyer David Melmed to clarify whether they can sing copyrighted songs on the show.
- Hilarious role-play with Conan as Paul McCartney (with surprise appearances by “Michael Jackson’s ghost”) devolves into absurdity:
“That’s not fing happening. No fing way. No, that’s a song I wrote…and you want to do what to ‘Let It Be’?” — Conan as Paul [61:31]
- David tries to seriously explain music clearance but is met with a barrage of jokes about denying everything, lying to rights holders, and “oral permission.”
- Judd and Conan heap praise on David for his actual solution-chasing:
“He is a genuine problem solver anytime you come to him with an issue.” — Judd [65:57]
Notable Quotes & Memorable Moments
- On aging in comedy:
“Just by being older, you’re creepy…if I just go into a dance club and do nothing but stand there…people will call the police.” — Judd Apatow [16:54] - Authenticity in improv:
“If you can tell an actor thinks they’re being funny, it instantly is awful.” — Judd Apatow [34:50] - On Mel Brooks’ right to mock Hitler:
“If anyone can, Mel Brooks can, because he’s a Jew who fought Hitler.” — Conan [21:35] - On Norm Macdonald:
“Norm doesn’t care in a way that frightens me.” — Andy via Conan [53:17] - Henson and warmth:
“It’s like Kermit telling you to f*** off.” — Judd [28:52] - About the impossibility of competing with viral moments:
“You look at [viral videos] and…there’s a couple of billion other people out there who are going to take a shot.” — Conan [43:24]
Key Timestamps
- 02:22 – The podcast’s unlikely appeal to children
- 04:43 – “Dynamic ad insertion” bit and absurd technical talk
- 08:12 – Losing child listeners over risqué humor
- 12:13 – Judd discusses Comedy Nerd and comedy memorabilia
- 16:54 – Judd on “the creepiness of aging”
- 18:53 – Mel Brooks: inspiration, documentary, and access to real emotion
- 27:50 – How a Jim Henson audition changed Judd’s career path
- 31:03 – Judd’s directing anxieties and Garry Shandling’s mentorship
- 33:33 – The pain (and gain) of improvisational filmmaking
- 34:50 – Where improv goes wrong in comedy movies
- 41:03 – Judd’s family comedy connections; Toni Fields story
- 43:56 – Viral videos and the arms race of contemporary comedy
- 47:43 – Judd’s traumatic “facts of life” book episode
- 51:47 – Sentimentality vs. staying in the moment; collaborative joy
- 53:17 – Conan on Norm Macdonald’s comedic nerve, legacy
- 58:26–68:38 – Legal comedy sketch about song royalties (highlights at 61:31, 63:03, 66:08)
- 65:57 – Team Coco’s lawyer gets praised for problem-solving
Tone & Style
The entire episode maintains Conan’s signature playful, self-deprecating, fast-paced tone—peppered with surreal tangents, improvisational chaos, and heartfelt reflections. Judd blends openness about his vulnerabilities and anxieties with whip-smart comic timing. Sona and Matt act as ideal comedic foils and supporters. Even the legal segment—ostensibly dry—erupts into parody and improvisation befitting the show's spirit.
Summary: Why Listen?
This packed episode is more than a recounting of showbiz memories; it’s an affectionate, meta-comedy exploration of creative anxiety, generational change, and what it means to be a lifelong “comedy nerd.” For those fascinated by the craft of comedy—as a performer, creator, or fan—it offers eye-opening, frequently uproarious exchanges, industry secrets, and a masterclass in making friendship (or at least playful friction) out of professional collaboration. And if you’ve ever wondered what happens when a lawyer tries to explain music rights to comedians, you’re also in for an unforgettable treat.