We Might Be Drunk – Episode 258: Judd Apatow

Release Date: November 17, 2025
Hosts: Mark Normand, Sam Morril
Special Guest: Judd Apatow
Location: NYC
Episode Description:
NYC comedians Mark Normand and Sam Morril host legendary writer, director, and producer Judd Apatow, with Bill Burr and Tom Segura joining throughout for an in-depth comedy roundtable covering road life, international comedy, peeves, drinks, the art of movie-making, and the modern state of comedy—with classic stories and plenty of laughter (and drinks).

Episode Overview

This episode is a comedic deep-dive into international touring, the culture of comedy across countries, and the inner workings of showbiz and film—all anchored by Judd Apatow, who opens up about his career, documentary projects, and philosophy of comedy. The group shares wild road stories, industry woes, and candid memories about icons like Rodney Dangerfield, Norm Macdonald, Diane Keaton, and Martin Scorsese, all in the show's signature loose, riff-heavy tone.

Key Discussion Points and Insights

1. Life on the International Comedy Road

• European Tours:

  • Tom Segura and Bill Burr exchange stories about recent tours—covering Oslo, Dublin, Paris, Athens, Rome, Milan, Stockholm, Helsinki, Barcelona, and Amsterdam.
  • Comic camaraderie abroad: comics “glom” to each other like seeing ambassadors in foreign lands.
  • Describing audiences: Stockholm described as “the best crowd” (06:12), while Helsinki and Amsterdam get called “tough, efficient, not expressive.”
  • Segura on Dutch crowds: “You get off and they’re like, 'It was amazing.' You’re like, tell your face. I’m dying up here.” (07:30)

• Cultural Observations:

  • Endless art and beauty, weird food (reindeer, whale), sauna cultures in Scandinavia, and struggles with foreign ATMs and the quest for drip coffee.
  • Debating the North American "bar culture" vs. European bar scenes: “I like the communal thing...whereas, like Milan, it’s just, you’re at a table outside with your group...I like the idea I can meet someone at a bar.” (09:41)

• Romantic Escapades:

  • Segura recounts a fun but failed attempt to invite a Liverpool woman to London—ending with her bailing out of fear of “being trafficked”—leading to a bit about the fear of trafficking fading as women age. (11:00)

2. Comedy Peeves and Customs

• European Peeves:
  • Trouble with unplanned museum visits; Van Gogh and Anne Frank House booked months out.
  • Difficulty getting good drip coffee: “I'm sick of the Americano...Give me a drip where you can just pour it out of a pitcher." (15:36)
  • Resenting slow hotel check-ins for weary travelers, complicated rental cars, and ATMs swallowing cards.
• Cultural Nitpicks:
  • American comics get mixed receptions socially: “my buddy Chase is trying to meet chicks, the second he says 'American', they’re like, ugh...I love when they ask me what's up with the tariffs, I'm like, I didn't do it!” (17:02)
• On “home”:
  • Vacation fatigue and returning home: “At what point do you go, I'm ready to get back? I think literally right at the end.” (09:24)

3. Modern Comedy and Showbiz Realities

• International Scenes:

  • Polish stand-up is booming—Segura wants to play Warsaw and Krakow (20:09).
  • Comics are drawn to “smaller venues where you sell out” vs. playing big, half-empty theaters: “Just put me in an 800 and we'd sell two. Great.” (22:03)

• Travel and Drinking:

  • The myth of “no hangover” with natural wine (“Turns out if you drink enough alcohol, you will still have a bad hangover.” (22:56))
  • Fears of leg cramps from travel drinking and lack of sleep—“Alone in my room, screaming.” (24:14)

4. Judd Apatow on Comedy, Docs, and the Industry

• Behind the Book:

  • Apatow’s new book discussed, described as “fancy” with thick, heavy, textured pages, and rare photos.
  • The rarity of photos pre-iPhone era—even major comedians have only “eight photos” from key times (34:48).

• Apatow’s Early Career:

  • Stories from writing for The Critic (42:16) and Larry Sanders, being the only non-Ivy League guy in the room.
  • How Larry Sanders was about “people who love each other, but show business gets in the way” (51:13).
  • Lessons in running writers' rooms and how to handle tough note-giving from execs (86:10).

• Movie War Stories:

  • Difficulty getting Anchorman made, Will Ferrell’s original script set on a mountain with chimpanzees and throwing stars (96:53).
  • Inviting Paul Thomas Anderson to help edit Funny People—and how a film’s "voice" can suddenly become someone else’s (80:44).

• Comedy as Art and Commerce:

  • The death of the “mid-budget” comedy film thanks to streaming and the end of DVD sales; optimism that a big hit could re-open the market.
  • Importance of strong dialogue in comedy films, referencing Clerks and Swingers as models for low budget, joke-driven dialogue (91:26).

5. On Comedy Legends: Reminiscence and Documentaries

• Rodney Dangerfield:

  • Anecdotes about seeing Rodney perform and hang-out stories: “He murdered as hard as you can murder...had such a mastery of the one liners.” (38:44)
  • Dangerfield’s legendary insecurity: “He always thought he wasn’t getting respect...maybe the guy who got the most respect out of everybody.” (38:15)

• Norm Macdonald Doc Announcement:

  • Apatow confirms he’s directing a Norm doc—drawn entirely from archive Norm footage, not talking heads: “We didn’t interview people...It’s just Norm.” (68:26)
  • Insights into Norm’s secret battles with cancer, gambling, and his comedic purity: “He was the purist.” (69:22)
  • On Norm’s legacy: “How many comedy-defining moments did Norm have that are world class, memorable, risky too...so many times that he did a shockingly, insanely original take on something.” (57:44)

• On the Importance of Docs:

  • Preserving the legacy: “If you don’t have these docs, I think in the future people won't know what these people were about at all.” (72:46)
  • Mention of Bill Hicks’ “American Scream,” docs on Joan Rivers, Rickles, Carlin, Mel Brooks, and more.

• Riffs on Cancel Culture and Comedians’ Legacies:

  • Jokes about reducing comedians to "one word": “You can't reduce people to one word who have contributed this much to comedy. Come on.” (04:00)
  • Nuances of dark material aging—and what’s now “SVU plot lines” were once comedy bits. (48:49)

Notable Quotes & Memorable Moments

International Comedy + Road Life

• On why comics bond abroad:

  • “It’s like seeing an ambassador.” – Bill Burr (01:15)

• Dutch Audiences:

  • “They’re not an expressive people.” – Tom Segura (07:17)
  • “You do the show and you’re like, ‘that’s it?’ What the fuck?” – Tom Segura (07:24)
  • “I always say it's like the girl you bang and… she was like, 'that was awesome.' Give me a moan.” – Bill Burr (07:35)

• Travel woes:

  • “No drip coffee. I’m sick of an Americano...give me a drip where you can just pour it out of a pitcher.” – Bill Burr (15:36)
  • “Slow hotel check in—been saying it for years.” – Bill Burr (28:54)
  • “My buddy Chase is trying to meet chicks, the second he says American, they’re like, ugh.” – Tom Segura (17:02)

Industry and Showbiz Wisdom

• Apatow on Larry Sanders:
  • “It’s about people who love each other but show business gets in the way...No one ever tells the truth to each other, and if they ever look someone in the eye and tell the truth, it’s a huge deal.” – Judd Apatow (51:05, 51:21)
• Handling Execs:
  • “If you find people who are really smart, like the people at Universal...They've given me tough notes that've been correct, and so we get each other.” – Judd Apatow (88:13)

On Comedy Legends

• Dangerfield’s meanness:

  • (When asked about what Rodney said of an old friend) “She was what? She was. She was what? She was.” – Rodney Dangerfield via Judd Apatow (37:31)

• Norm Macdonald’s Integrity:

  • “He was a purist. I could come out and say [I have cancer] and would get a bunch of clicks...but I’m just gonna keep being funny.” – Norm, paraphrased by Bill Burr (69:22)

• Comedians’ legacies:

  • “If there’s a Norm Macdonald doc, in 30 years someone might watch, and that's your path into going down the rabbit hole to look at everything.” – Judd Apatow (73:00)

Timestamps – Quick Reference

• 00:06 – 07:58 — Travel tales: Europe, Paris, Rome, Dublin, Athens, cultural faux pas
• 09:24 — Discussing bar cultures: Milan vs. Dublin/Liverpool
• 11:00 — Segura’s “trafficking” story from Liverpool
• 15:36 — Drip coffee rant
• 17:02 – 20:09 — Americans abroad, Polish comedy, international scene
• 22:50 — “Natural wine gives you hangovers too”
• 28:54 — Slow hotel check-in peeve
• 34:48 — Old photos: “before iPhone, whole eras not captured”
• 37:31 — Rodney Dangerfield’s insult
• 51:05 — What Larry Sanders was about
• 57:44 – 62:04 — Norm Macdonald doc: “so many times he did a shockingly, insanely original take...”
• 68:26 — Norm doc structure: “It's just Norm”
• 79:01 — State of comedy movies, mid-budget genres, AI, and horror competition
• 80:44 — Bringing in Paul Thomas Anderson for Funny People
• 86:10 – 88:55 — Taking network notes; the struggle, failures, resistance, and finding the right partners
• 93:19 — Scorsese doc, legacy, “King of Comedy” as favorite
• 96:53 — Anchorman’s original script with “chimpanzees and Chinese throwing stars”
• 98:21 — On making movies to “just have access” to the process, being on set for Anchorman
• 101:19 – 102:15 — Behind Bridesmaids, Kristen Wiig’s breakout
• 108:43 — Working with Warren Beatty, comedy cameos

Final Notes

• The episode is a wide-ranging, high-energy hang blending road stories, comedy nostalgia, industry inside-baseball, and honest reflections on art and business—all with classic, sharp wit.
• Apatow’s insight into the persistence needed in showbiz, and the importance of documentation (via books and docs), is especially resonant for aspiring comedians and film lovers.
• Standout segments include stories about Norm Macdonald, stories from the golden age of alt-comedy in LA, the nature of running writers' rooms, and how global comedy (and travel culture) is evolving.
• The episode closes with plugs for everyone’s upcoming gigs and a heartfelt endorsement of Judd's new book, Comedy Nerd, positioning it as essential reading for anyone interested in comedy’s past and present.

Recommended for:

• Fans of stand-up and comedy history
• Anyone interested in the creative process, movies, and insider showbiz tales
• Stand-up comics (and comedy writers) navigating the modern industry
• Documentary lovers and "comedy nerds" of all stripes

“If you don’t have these docs, I think in the future people won’t know what these people were about at all.” — Judd Apatow (72:46)