Sean Penn

Sean Penn played the memorable stoner Jeff Spicoli in Fast Times At Ridgemont High, though his roles took more of a serious turn afterward. In the mid-90s, he had a memorable performance in Dead Man Walking and then went on to win two Academy Awards for his performances in Mystic River and Milk.

Beyond his movie career, which is pretty stagnant these days, Penn has become known for his political activism. He has become a prominent voice in progressive circles and was public about his pushback of the U.S. government’s handling of Hurricane Katrina. In 2022, he was active in coverage of the Russian-Ukraine crisis.