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Bobby Lee: I Wish I Knew
29 October 2026

Bobby Lee: I Wish I Knew

Blocks: I Wish I Knew w/ Neal Brennan

About
Bobby Lee joins Neal Brennan to share what he wishes he knew sooner: worrying about his career wouldn’t change its course, asking for help mattered, and the life he built could look different from the one he imagined. He still likes the MadTV tattoo, though.



They talk about Bobby’s first stand-up special, learning to watch himself on screen, sobriety, his father’s death, and the unexpected emotional impact of a trip to Build-A-Bear. Plus: homemade glue hands, a swimming pool full of coffee, Neal’s place in the comedy police, and whether he’s allowed to speak at Bobby’s funeral.



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CHAPTERS

0:00 Aging and Korean Skincare

1:16 The LeBron James of Podcasting

3:20 Navigating Hollywood and the Comedy Police

9:39 Why Bobby Waited to Make a Stand-Up Special

20:29 Wishing He Worried Less

23:35 Gluin'

26:02 Filling His Swimming Pool With Coffee

30:18 Sobriety 

33:23 Sensitivity, Shane Gillis, and Public Shame

36:13 Learning to Be Proud of Himself

40:25 Why Bobby Avoids Negative Comments

42:40 Was All That Worry Worth It?

48:14 Sponsor: Lucy

51:07 The Real Bobby Versus His Public Persona

52:35 Letting Go of the Movie-Star Dream

53:19 Losing His Father and Relapsing

57:38 Asking for Help and Starting Therapy

59:42 Recognizing Childhood Trauma

1:01:02 Intensive Therapy and Build-A-Bear

1:04:39 Porn, Relationships, and Regret

1:10:22 Family, Self-Blame, and Avoiding Conflict

1:12:04 Can Neal Speak at Bobby’s Funeral?

1:13:28 The Future of Bad Friends and TigerBelly



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Follow Neal Brennan: https://www.instagram.com/nealbrennan

https://twitter.com/nealbrennan

https://www.tiktok.com/@mrnealbrennan



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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