Fail Again: Sean Penn and the Squared-Away Individual

Fail Again: Sean Penn and the Squared-Away Individual

From Fail Better with David Duchovny by Lemonada Media

January 27, 2026 · 59 min

About this episode

David Duchovny interviews Sean Penn about his life, career, and the influences that shaped him.

This episode originally aired June 18, 2024 There are few actors left who embody the ethos of old Hollywood. Sean Penn is one of them. We got together at his place for a face-to-face exploration of Sean’s life and career. We discussed how his childhood in Malibu helped him create the iconic Jeff Spicoli, and how his first acting coach still shapes him today. We speak of his friends — Brando, DeNiro, and Scorsese — legends whose reputations, work ethic, and willingness to keep learning shaped their characters and their lives. Spending an hour in his presence is a masterclass in the pursuit of being a better creator, and a better human. Follow me on Instagram at @davidduchovny. Stay up to date with Lemonada on Twitter, Facebook and Instagram at @LemonadaMedia. Joining Lemonada Premium is a great way to support our show and get bonus content. Subscribe today at bit.ly/lemonadapremium. And if you want to continue the conversation with other listeners, join the My Lemonada community at https://lemonadamedia.com/mylemonada/ For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors. See omnystudio.com/listener for privacy…

People in this episode

Host: David Duchovny

Guest: Sean Penn

Topics covered

  • Hollywood
  • acting
  • creativity
  • personal growth
  • iconic characters

Keywords

  • Sean Penn
  • David Duchovny
  • Hollywood
  • acting
  • creativity
  • Jeff Spicoli
  • Brando
  • DeNiro
  • Scorsese

Mentioned in this episode

Places: Malibu

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