Sean Penn

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

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

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 ...

Actor Sean Penn feels relieved to be Conan O’Brien’s friend.

Sean sits down with Conan to discuss finding a balance between art and advocacy, the modern preoccupation with optics over empathy, and working with CORE to make positive change in the world. Later, Son ...

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

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 ...  Show more