Sean Penn (Milk, Fast Times At Ridgemont High, I Am Sam, Into the Wild) is an American actor, director, screenwriter, producer, author and humanitarian. Sean chats with the Armchair Expert about recognizing limitations, the freedom he finds in writing books and the impact of cancel culture. Dax wonders what drove Sean toward humanitarian work and Sean talks ... Show More
Yesterday
Ray Madoff (on how billionaires avoid taxes & threaten capitalism)
Ray Madoff (The Second Estate, Immortality and the Law, Practical Guide to Estate Planning) is a Boston College law professor, author, and tax-policy expert. Ray joins Armchair Expert to discuss being a proudly mediocre high school student, reluctantly trading philosophy for law ... Show More
2h 26m
Aug 31
Gal Gadot
Gal Gadot (The Runner, Wonder Woman, Fast & Furious) is an actor, action star, and former pageant winner. Gal joins Armchair Expert to discuss unexpectedly winning a beauty pageant, being thrust onto the front page of the New York Post at 21, and surviving cerebral venous thrombo ... Show More
1h 59m
Aug 2021
“Sean Penn”
<p>Yo, folks– it’s Sean Penn. Humanitarian, actor, director, writer, and surfer, Sean Penn joins us for a chat and a smoke break. We discuss his new film, his old films, and everything in between– like the world. Plus Sean H. formally thanks our guest for teaching his educators ... Show More
1h 3m
May 2025
S5 EP2: Sean Penn on dining with Jack Nicholson and Putin, run-ins with the paparazzi, and his relationship with Zelenskyy
Louis travels to Los Angeles to sit down with Hollywood heavyweight and international adventurer, Sean Penn. Renowned for award-winning roles in films like Milk, I Am Sam and Carlito’s Way, Sean discusses his colourful life and career, including dining with Jack Nicholson and Vla ... Show More
1h 24m
Jan 2023
Sean Penn | Club Random with Bill Maher
Bill Maher and Sean Penn randomly riff on which one of the Three Stooges Sean was going to play, their opposing beliefs on personal health, why Sean is attracted to dangerous places, Oliver Stone, Sean’s crush on Diane Sawyer, Sean’s relationship with the paparazzi, Sean’s love o ... Show More
1h 43m
Dec 2023
Sean Penn on Art, Activism, and the Urgency of Ukraine
<p>Sean Penn shares his profound experiences from Ukraine, revealing the stark realities of war and the resilient spirit of its people. Penn and Bernthal delve into a deep conversation about the power of community in the face of adversity, the nuances of acting and documentary fi ... Show More
1h 34m
Sep 2019
A Sox–Yanks Power Flip and Biden's Struggles With JackO, Plus Sean Penn's First BS Appearance
HBO and The Ringer's Bill Simmons is joined by his buddy JackO who gives his thoughts on the Red Sox firing their GM David Dombrowski, the surging Yankees, the Democratic presidential candidates, and more (4:10). Then Bill sits down with Academy Award-winning actor Sean Penn to d ... Show More
1h 26m
Sep 2023
Seth Rogen (Re-release)
Seth Rogen [Superbad, Pineapple Express, An American Pickle] talks with Anna about lying to the press, wishing he could sing, taking a long ocean voyage, getting high on Mars, and more. Then Dan Savage from Savage Lovecast makes an appearance to provide some qualified advice as h ... Show More
54m 3s
Mar 2017
Michael Peña
This week on Unqualified, Anna and Sim sit down with the very funny, Michael Peña (Ant-Man, End of Watch, The Martian)! They talk about diversity in Hollywood, EDM and Michael's new film CHiPS! They then call Michelle, who's trying to decide whether or not to start having kids, a ... Show More
1h 34m