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Judd Apatow: I Wish I Knew
12 November 2026

Judd Apatow: I Wish I Knew

Blocks: I Wish I Knew w/ Neal Brennan

About
Judd Apatow joins Neal Brennan to talk about what he wishes he knew sooner: how to observe his own mind, recognize his triggers, and stop treating every career setback like a threat to his survival.

They also discuss revisiting The 40-Year-Old Virgin after 20 years, the mystery of Norm Macdonald, Maria Bamford’s honesty, and what Judd thinks the point of his documentaries are. Plus: living with Adam Sandler, seeing Frank Sinatra on mushrooms, an unexpected encounter with Jesus on ayahuasca, and the freedom of realizing you were wrong.
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CHAPTERS
00:00 Introducing Judd Apatow

01:11 Rewatching his own movies—and finally feeling proud

08:24 The mystery of Norm Macdonald

22:09 Maria Bamford’s comedy and honesty

28:59 Sponsor: Huel

31:58 Sponsor: Superpower

34:14 Sponsor: Tushy

36:31 What makes a great comedy documentary?

40:08 Honesty, privacy, and telling someone’s story

43:41 Can comedy change society?

48:33 Seth Rogen and the point of Judd’s movies

52:21 What Judd wishes he knew about directing

53:50 Collaborators, childhood, and wanting things to last

59:02 Sponsor: Ethos

1:00:56 Sponsor: Rugiet

1:02:55 Learning to observe your own mind

1:04:40 Career anxiety

1:10:54 Wishing he’d explored psychedelics sooner

1:13:57 Ayahuasca and seeing Jesus

1:15:31 The freedom of being wrong

1:18:45 Friendship, change, and letting go

1:23:48 Being present for the people you love

1:25:59 Politics, worry, and the limits of control

1:30:34 Faith, surrender, and enjoying your life
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Watch Neal Brennan: Crazy Good on Netflix: https://www.netflix.com/title/81728557

Watch Neal Brennan: Blocks on Netflix: https://www.netflix.com/title/81036234

Theme music by Electric Guest (unreleased).

Edited by Will Hagle (wthagle@gmail.com)

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