Podcast Summary: The Interview (NYT) — "Sean Penn Let Himself Get Away With Things for 15 Years. Not Anymore."

Date: September 27, 2025
Host: David Marchese
Guest: Sean Penn

Overview

This episode features a candid, wide-ranging conversation with actor, director, and activist Sean Penn, covering his return to passionate filmmaking with Paul Thomas Anderson’s new film One Battle After Another, his humanitarian work with CORE, the roots and uses of his anger, his disillusionment and rekindled love for acting, reflections on American civic crisis including the recent assassination of Charlie Kirk, and the complex role of the artist in an unstable world. The discussion balances personal insight, political critique, and Penn’s signature mix of candor, humor, and self-awareness.

Key Discussion Points & Insights

1. The "Man Cave" and Memory (03:02)

• Setting: Interview takes place in Sean Penn’s home room, filled with memorabilia—described as his "man cave" or “the Jon Penn version of Elvis’s jungle Room.”
• Penn on the room’s meaning:

  “It’s a room in process of curation...it’s like if someone had a lot of post-its to remind them where they put their keys, which makes me very happy.” (03:06)

2. Art vs. Activism: Is There a Difference? (04:01–06:04)

• Why does Penn still make movies when so engaged in activism?
• Penn’s philosophy:

  “It’s all exactly the same thing, whether it’s acting or working with CORE or...woodwork...It just feels like, which hammer are you picking up on that day to hopefully make a contribution.” (04:34)

• Impact of film:

  “If an audience member goes to a movie and...leaves them feeling, let’s say, less alone...that’s no different than to rebuild housing for someone. It’s all kind of one thing.” (05:16)

3. One Battle After Another: Genesis and Themes (06:07–08:09)

• Draw to the project: Longstanding desire to work with Paul Thomas Anderson; thrill at the script and cast.

  “I could not have been happier with what he [Anderson] had decided to take on. And I immediately told Paul, you know, tell me where to go.” (07:25)

• Film’s depiction of America: Chilling vision of a fascist, white nationalist regime.
• Penn on America’s unfulfilled promise:

  “What is America? Right. Which, by the way, of course, we know, never fulfilled its promise to everybody...It takes time to grow.” (08:09)

• Penn’s family history: Father blacklisted despite war heroism—acceptance of “speed bumps in the making of a country.” (08:58)

4. Acting Burnout and Renewal (11:36–13:41)

• Penn describes a 15-year malaise about acting:

  “I got two gifts in one year that broke a 15 year sort of depression about the movies.” (11:46)

• What changed?

  “It’s not enough to work with people you respect and like. You want the same thing you find in family. You want to be people you love.” (12:33) “I kept taking these jobs that I thought were good...and I was missing my family, whatever that meant. Literally, my dog. And I said, what the fuck am I doing here?” (13:00)

• Did his work suffer? “No question about it. You...get away with too much.” (13:44)

5. The Influence of Older, Rebellious Artists (15:37–17:43)

• Why Penn sought out old rebels: He always felt “77” years old inside, found kinship in older men like Nicholson, Brando, Bukowski.

  “It’s easier...to have a friendship where you’re not going to be frowned upon if you say, hey, want to get a drink?” (16:22)

• On green juice vs. whiskey: “There’s nothing wrong with anything anybody wants to do that doesn’t hurt someone else...I like to share a drink with someone.” (17:06)

6. Childhood, Trauma, and Making His Own Demons (17:43–19:31)

• Debunking myth of unhappy childhood:

  “Psychiatrists have been pushing...trying to find that capital T trauma in my childhood. It’s not there. I made every demon door in my life as a young adult and forward. I did it myself.” (18:34)

7. Anger and Competence (21:20–23:41)

• Origin of Penn’s anger: Frustration with mediocrity/incompetence in daily life.

  “Incompetence drives me out of my fucking mind. It triggers me on a level you can’t imagine. I start to equate my soul with a volcano.” (22:19)

• Productive use of anger: Dedicated to competence as a way to “fight the opposite.” (23:04)
• Professional pride and expectations:

  “That all describes pride. And I guess that’s another thing I could say, I think is all too absent too much of the time.” (23:59)

8. Famous Macau Incident (24:31–27:10)

• Penn retells the story of allegedly dangling a paparazzo over a balcony:

  “We didn’t put him past his waistline over that balcony, and there was never an intent to drop him off of it.” (25:35)

  • The real escape was much less dramatic (“like the ferry”) than rumors suggested.

9. Hypocrisy and Contradiction (27:22–28:54)

• On American hypocrisy:

  “Hypocrisy is the primary experience of American life...I am certainly willfully contradictory.” (27:32, 28:43)

• Penn’s biggest contradiction:

  “Ukraine deserves our full support in their killing people. That’s contradictory to almost anything else I would say or espouse. I don’t think there’s another solution.” (28:54)

10. Assassination of Charlie Kirk & American Civic Crisis (32:34–36:12)

• Reacting to the killing of Charlie Kirk:

  “This one seems different...Charlie Kirk...was one of these people who...truly believed everything that we disagreed on. I didn’t get the sense that he was one of these snake oil salesmen. I think we need that guy. We need that debate.” (34:13)

• On polarization and violence:

  “We’re taking the easy, chicken shit road out when we start to put this murderer...as the best argument you got?” (36:12)

11. On Trump, Zelensky, and Putin (36:16–38:38)

• Asked if Trump has beliefs: “I am not able to discern them.” (36:16)
• Zelensky’s attitude toward America/Trump: Penn says not his place to speak for Zelensky. (36:50)
• Putin’s character:

  “By now I find him [Putin] transparent and almost uninteresting...His inability to face a new world makes him static.” (37:29, 37:44)

12. Evolving Politics (38:55–40:47)

• Penn on his political development:

  “I idealize humanity less. And in that I understand we’re going to keep killing each other for the foreseeable future. So I’m a little more pragmatic about how to support the ability to do terrible things when we have to.” (38:55)

• On stagnation:

  “If you’re at the same place politically when you’re older as you were when you’re younger, I think you’re adding a problem to the world.” (38:55)

• Anecdote from safari guide:

  “Anything that remains static dies.” (39:27)

13. Artists, Boycotts, and Humanitarian Work (40:48–43:58)

• On industry boycott of Israel: Not previously aware; generally “allergic to movements or group things” due to fear from "baby killer" Vietnam rhetoric.

  “If I’m going to boycott something, I kind of want to do it myself and see if other people do the same. But I think there’s time and place for it...” (41:38)

• On Netanyahu’s government:

  “...the far right and Netanyahu are truly criminal problems. That’s got nothing to do with...the better intersects between Israel and the United States. This current administration is an enemy of every state and humanity at this current Israeli administration.” (42:15, 42:43)

• CORE and Gaza:

  “We have not to date [engaged in Gaza]. My feeling right from GO was I don’t trust any of our governmental organizational contacts on either side. And I’m not ready to ask our people to go there.” (43:41)

14. Celebrity’s Double-Edged Sword in Activism (44:04–46:34)

• On his Rolling Stone 'El Chapo' piece:

  “It didn’t matter because I should have seen that coming...You have to consider the optics when you step out into that ring for sure. And so you take lessons learned and try to do it better.” (45:37–46:11)

• On limits of what he can share: Protects confidences, doesn’t want to “adversely affect” others. (46:15)

15. Motivations: Why Be a “Man in the Arena”? (47:02–49:34)

• Influences: Cites Muhammad Ali, Bob Geldof, Bono, George Harrison, George Clooney as activist inspirations.

  “You talk about somebody who stands with empathy...he’s an extraordinary, extraordinary human being [Bono].” (48:16)

• On his father: Hero and model of idealism and kindness, despite suffering (blacklist) after WWII.

  “He’d just say, everybody has their own truth, kid.” (49:36)

16. Hope, Anger and Living with Joy (50:03–52:04)

• Is he motivated by anger or hope?

  “I don’t need the rage to get me to a clarity of knowing how evil and obscene it is...Frustration is with those who are not willing to be sober enough to recognize our sacred duty to support the defense of Ukraine.” (50:37) “I wake up every fucking day...This one is driving me from the time I wake up. And all I see is that right now this is still a fucking magic trick of a beautiful cosmos...and I am going to fucking enjoy it every day. And I do, you know, sorry to those who would have me do otherwise.” (51:28)

Notable Quotes & Memorable Moments

• On creative and humanitarian purpose:

  “Your work as an actor is exactly the same job as your work as a craftsman or a welder or core representative. It just feels like, which hammer are you picking up on that day to hopefully make a contribution.” (04:34)

• On nostalgia for older friends:

  “When I look in the mirror, I’m waiting for that guy [77] to show up. My father died at 77. I had already chosen 77.” (16:22)

• On responding to world ugliness:

  “We’re in a period of incredible unpredictability and chaos. And ugliness. A lot of ugliness. Stupidity over dependence on technology, misuse of it, disconnection.” (09:00)

• On being fueled by anger:

  “Incompetence drives me out of my fucking mind. It triggers me on a level you can’t imagine. I start to equate my soul with a volcano.” (22:19)

• On American contradiction:

  “Ukraine deserves our full support in their killing people. That’s contradictory to almost anything else I would say or espouse. I don’t think there’s another solution.” (28:54)

• On violence and national division:

  “Charlie Kirk...truly believed, everything that we disagreed on. I didn’t get the sense that he was one of these snake oil salesmen. I think we need that guy. We need that debate. We aren’t perfect.” (34:13)

• On activism models:

  “Muhammad Ali, Bob Geldof, Bono. George [Harrison]...You talk about somebody who stands with empathy...he’s an extraordinary, extraordinary human being.” (47:30–48:16)

• On enjoying life despite trouble:

  “...right now this is still a fucking magic trick of a beautiful cosmos to be gifted with and I am going to fucking enjoy it every day.” (51:28)

Timestamps for Major Segments

• 03:02 — Penn describes his “man cave,” curation, and remembering life.
• 04:34 — On the unity of art and humanitarian work.
• 07:25 — Deciding to do One Battle After Another.
• 08:09 — On America’s perennial unfulfilled promise.
• 12:33 — Losing and rediscovering the joy of acting.
• 16:22 — The “77-year-old” inside Sean Penn.
• 18:34 — His trauma-free childhood and embracing luck.
• 22:19 — Anger at incompetence and its impacts.
• 25:35 — Macau paparazzo incident clarified.
• 27:32 — Hypocrisy, contradiction, and “Ukraine deserves our full support.”
• 34:13 — Reaction to Charlie Kirk’s assassination.
• 36:16 — On Trump, Zelensky, and Putin’s character.
• 38:55 — Penn’s evolving, less idealistic politics.
• 41:38 — On boycotts, Israel, and resistance to groupthink.
• 43:41 — CORE’s caution in entering Gaza.
• 45:37 — Limits and pitfalls of celebrity activism.
• 47:30 — Penn’s humanitarian and activist inspirations.
• 49:36 — Influence of his father, “everybody has their own truth.”
• 51:28 — Waking up grateful and hopeful despite the world’s pain.

Summary Prepared For:
Listeners seeking an in-depth, unfiltered glimpse into Sean Penn’s mindset, his analysis of the present American and global moment, creative renewal, and the messy, inspiring contradictions of being an engaged, outspoken artist.