Fail Again: Sean Penn and the Squared-Away Individual

2026-01-27

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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...

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.

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