Fail Again: Sean Penn and the Squared-Away Individual

Fail Better with David Duchovny

Grace Cohen-Chen

Society & Culture

4.6 • 534 Ratings

🗓️ 27 January 2026

⏱️ 58 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 information. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	It's morning in New York.
0:02.8	Oh, God.
0:06.2	Hey, everybody.
0:07.3	I'm Mandy Patinkin.
0:08.7	And I'm Catherine Grady.
0:09.8	And we have a new podcast.
0:11.7	It's called Don't Listen to Us.
0:14.1	Many of you've asked for our advice.
0:16.1	Tell me, what is wrong with you people?
0:19.2	Don't listen to us.
0:20.3	Our Take It or Leave a Advice show Wednesday out now, a Lemonada Media Original.
0:30.3	The actors that I respected or loved growing up, well, not growing up, but when I started acting, you didn't know so much about them.
0:40.2	And that was important for their acting because then they could become other people for you up there.
0:44.5	And then we entered into the stage of history where we wanted information on everything.
0:50.2	And then we entered into the Internet age where we have information on everyone and everything. And then we entered into the internet age where we have information on everyone and
0:54.5	everything. And then we entered into the age where celebrities share freely information, whether
1:01.7	it's curated or not, we don't know about everything and anything. And I still have this
1:10.0	kind of sense of privacy about me that it's not arrogance and it's not secrecy.
1:16.4	And I think Sean shares it because he's from the same generation as me.
1:22.0	And it's a protectiveness of the job, of the magic trick of acting.
1:28.2	The less you know about me, the more freedom I have to become someone else.
1:33.0	And that was a fear of doing this podcast, was, you know, the more I talk about myself
	...

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