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 about the human desire for wanderlust. The two talk about the point at which assets become embarrassments, their mutual love of Bukowski and Sean's disapproval of insincerity. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.