Podcast Summary: The Daily – ‘The Interview’: Sean Penn Let Himself Get Away With Things for 15 Years. Not Anymore.
Host: David Marchese, The New York Times
Guest: Sean Penn
Date: September 27, 2025
Episode Focus: An expansive, candid conversation with actor and activist Sean Penn, exploring his personal evolution, creative resurgence, politics, humanitarian work, and his perspective on the state of America and art.
Overview
This episode presents an in-depth interview with Sean Penn centered on his new film "One Battle After Another," his complex relationship with acting, his humanitarian efforts, and his frank views on political and cultural crises. In a wide-ranging discussion, Penn reflects on past regrets, his evolving purpose, activism, and the role anger and contradiction play in his life. The episode is marked by self-awareness, irreverence, and Penn’s refusal to shy away from controversy or vulnerability.
Setting the Scene & Initial Impressions
[02:38–03:52]
- Interview conducted in Penn’s Malibu home, a room filled with memorabilia and symbols of his life, “in process of curation.”
- Penn’s “man cave” reminds him of people and moments he's lived, like “post-its to remind them where they put their keys.”
- David Marchese describes Penn’s demeanor: “sincere, funny, a little crotchety, self-aware about his own grandiosity and as always, unafraid to let it fly.”
Notable Quote:
Sean Penn [03:01]: “When I’m not on my feet, I’m in this room… It’s the room in my house where I feel most comfortable. But it is also a room in process of curation… So it’s a room that in its own way, it’s like if someone had a lot of post-its to remind them where they put their keys, which makes me very happy.”
On Art, Purpose, and the Utility of Making Movies
[03:55–06:00]
- Penn draws no real line between art, humanitarian work, or woodworking: all are about “making a contribution.”
- Sees acting and aid as “picking which hammer up on that day”; both can offer “relief” or make someone “feel less alone.”
- Acting can provide the same kind of presence as rebuilding someone’s home.
Notable Quote:
Sean Penn [04:29]: “In a way, I’d always kind of felt intuitively that it’s all exactly the same thing… Your work as an actor is exactly the same job as your work as a craftsman… if an audience member goes to a movie and recognizes something ... it’s a similar relief and a similar moment of being able to breathe…”
Collaborating with Paul Thomas Anderson & Choosing Projects
[06:00–07:32]
- Longstanding relationship with Paul Thomas Anderson led to immediate enthusiasm for "One Battle After Another."
- Had previously declined “Punch Drunk Love” because he felt he’d want the part Adam Sandler played.
- Describes being “could not have been happier” with Anderson’s script and with Leonardo DiCaprio’s attachment.
Reflections on America: Politics, History, and the State of the Nation
[07:34–09:21]
- The film’s depiction of a fascistic America is not viewed as alternate reality; Penn reflects on his optimism and realism about the US.
- References his father’s blacklisting as emblematic of “speed bumps in the making of a country.”
- Acknowledges “ugliness, stupidity, over dependence on technology, misuse... disconnection,” but also emphasizes resilience and “the fight for freedom.”
Notable Quote:
Sean Penn [08:28]: “My father was blacklisted by the country he fought and risked his life for ... and he couldn’t even get any bitterness going towards it. He just said, hey, speed bumps in the making of a country.”
Character Analysis: Colonel Steve Lockjaw & Human Nature
[09:36–11:24]
- Penn’s film character is “a stew of perversions and insecurities”; reflects on learning from history as lived experience, not just study.
- Emphasizes idealization leads to cynicism; sees his character as someone who “worships at the church of lethality.”
- Draws from the words of former Uruguayan President Pepe Mujica about the inevitability of repeating history.
Creative Burnout, Revival, and the Search for Meaning in Work
[11:24–15:32]
- Penn’s creative depression lasted about 15 years; revived by projects "Daddio" and "One Battle After Another."
- Describes searching for the “family” feeling in work, not just good scripts/directors.
- Felt he was “faking it” when taking jobs “about good subjects with good directors” but missing authentic connection.
- Admits his work suffered; grew resentful and believed others could sense it.
Notable Quote:
Sean Penn [13:39]: “You are given automatic cover if you’ve had, you know… once you represent a certain kind of quality stamp and you get away with too much.”
Mentors, Rebellious Friends, and the Lure of the Outsider
[15:32–17:38]
- Surrounded himself with older, rebellious figures such as Nicholson, Brando, Bukowski, and Harry Dean Stanton.
- Attracted to “interesting guys who... were incredibly generous towards me as friends and also as, you know, encouragers, supporters of the kinds of stories I wanted to tell…"
- Candidly discusses feeling “77” internally, linking it to his father’s death at that age.
Notable Quotes:
Sean Penn [16:14]: “It’s 77… I can’t wait. I know that guy. Like, that’s that… When I look in the mirror, I’m waiting for that guy to show up. My father died at 77. I had already chosen 77.”
On Childhood, School, and the Origin of His Drive
[17:38–20:39]
- Pushes back against psychoanalytic claims his happy childhood embarrassed him; says trauma and demons were self-created.
- Hated school, which he describes as “barbaric enforcement of mandatory schooling,” stealing time from surfing and childhood joy.
- Saw himself as someone eager to move past childhood’s constraints.
On Anger, Hypocrisy, Incompetence, and Contradictions
[21:01–28:49]
- Commonly described as having “a real anger inside you”; Penn says his frustration is at human incompetence—“Incompetence drives me out of my fucking mind.”
- Sees pride and professionalism as missing in society.
- Freely admits to his hypocrisy and contradiction, noting: “Hypocrisy is the primary experience of American life.”
Notable Quotes:
Sean Penn [21:23]: “My problem is with humans… Incompetence drives me out of my fucking mind.”
Sean Penn [28:49]: “Ukraine deserves our full support in their killing people. That’s contradictory to almost anything else I would say or espouse.”
Notorious Incidents & Celebrity Mythos
[24:21–27:05]
- Discusses the infamous incident of dangling a paparazzo in Macau in 1986: insists it was exaggerated; describes escape to Hong Kong via “jet foil” ferry, not as dramatic as urban legend suggests.
The Second Conversation: Violence and the American Moment
[32:00–34:56]
- Interview resumes post-Charlie Kirk assassination, which Penn describes as feeling distinct from other high-profile killings—“This one seems different.”
- Laments America’s polarization, blames “power hustling of politics and media” but insists individuals have more in common than is expressed publicly.
- Believes strong, sincere debate—even with opponents like Kirk—is vital to democracy.
Notable Quote:
Sean Penn [34:34]: “If somebody really believes something, that’s your friend… if somebody believes that a human being starts at conception. If you can’t understand that concept, you’re just stupid. And if you’re not willing to tolerate the concept… you’re just stupid.”
On Trump, Zelenskyy, Putin, and International Politics
[35:52–38:18]
- Penn cannot discern “beliefs” held by Trump.
- Discusses making “Superpower,” documentary on Zelenskyy; keeps details about Zelenskyy’s views on US-Ukraine politics private.
- Finds Putin “transparent and almost uninteresting”; accuses him of being “static,” unable to face a new world.
The Evolution of Penn’s Politics
[38:35–40:09]
- Views himself as less idealistic, more pragmatic about violence and support for difficult causes.
- Believes remaining static—politically or personally—is death (“Anything that remains static dies”).
Artists, Activism, and Boycotts
[40:32–42:33]
- Shares skepticism toward group movements, including cultural boycotts such as the Hollywood pledge against Israel.
- Favors individual action over collective slogans, but keeps an open mind depending on the situation.
Notable Quote:
Sean Penn [41:03]: “Typically, I… have an allergy to movements or group things… If I’m going to boycott something, I kind of want to do it myself and see if other people do the same…”
Humanitarian Work with CORE
[42:33–43:38]
- CORE has not worked directly in Gaza post-October 7, 2023, due to dangerous conditions and mistrust of operating frameworks.
- Open to future involvement but prioritizes safety for staff.
Reflections on Celebrity and Advocacy
[44:06–45:55]
- Acknowledges potential for celebrity to both help and harm the causes he spotlights.
- Points out that mainstream journalism too can “adversely affect society” when focused on “editorial screaming matches.”
Influences: Activists and Family
[47:09–49:14]
- Credits Muhammad Ali, Bob Geldof, Bono, and George Harrison as modeled examples of high-profile activism.
- Father, screenwriter and war veteran Leo Penn, especially influential for remaining gentle despite adversity and never being “bitter,” even after blacklisting.
Notable Quote:
Sean Penn [48:44]: “You know, he’s been my hero in everything. Most significantly, I think just a guy who remained gentle and never entered bitter…”
Motivation, Rage, and Joy in Later Life
[49:29–51:44]
- Discusses how sadness, but not depression, marks his later years; remains deeply motivated to be a “value add.”
- Finds joy in life and is “feeling great,” despite awareness of world crises.
Notable Quotes:
Sean Penn [51:17]: “I wake up every fucking day. This eye is clear about the threat to the environment, the anguish people are going through… but I am feeling great.”
Memorable Moments & Quotes
- On connecting art and aid: "It's all kind of one thing... It's like, which hammer are you picking up that day?" [04:29–05:55]
- On 15 years of creative burnout: “I just felt like, maybe I’m done with all this.” [13:26]
- On polarization and violence: "We need that guy. We need that debate… If somebody really believes something, that's your friend." [34:34]
- On activism after celebrities: "Muhammad Ali, Bob Geldof, Bono, [George Harrison]... I was at Live Aid... what it led to was astonishing." [47:09–47:47]
- On his father’s gentleness despite injustice: "He’s been my hero in everything. Most significantly… a guy who remained gentle and never entered bitter." [48:44]
- On getting up in the morning: “I am going to fucking enjoy it every day. And I do, you know, sorry to those who would have me do otherwise.” [51:40]
Timestamps for Key Segments
- [03:01] – Sean Penn describes his personal sanctuary at home.
- [04:29–06:00] – Penn’s philosophy: art and activism as facets of the same purpose.
- [09:36–11:24] – Interpreting his new character and the lessons of history.
- [13:36–15:32] – On burnout, faking it, and rediscovering the joy of acting.
- [16:14] – Penn talks about always feeling “77” inside.
- [21:23] – Anger: “Incompetence drives me out of my fucking mind.”
- [28:49] – Contradiction: “Ukraine deserves our full support in their killing people.”
- [32:57–34:34] – On the aftermath of Charlie Kirk’s assassination.
- [38:35–40:09] – Growth: “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.”
- [47:09] – Citing major public figures who inspired his activism.
- [51:40] – “I am going to fucking enjoy it every day.”
Conclusion
This conversation with Sean Penn is rich in its vulnerability, candor, and the willingness to embrace contradiction. Penn discusses his personal and creative journey, the darkness and hope of American life, the burdens and opportunities of activism, and his refusal to become static or disengaged. The interview is a mosaic of reflection, humor, and challenge—offering insight into the mind of one of Hollywood’s most complicated and outspoken figures.