Sean Penn

Sean Penn appeared as an extra in a 1974 episode of Little House on the Prairie, directed by his father, Leo Penn. He launched his film career with Taps (1981), followed by his breakout role as Jeff Spicoli in Fast Times at Ridgemont High (1982), helping popularize the word “dude.” He then earned acclaim for his dramatic turn in Bad Boys (1983).

He portrayed Andrew Daulton Lee in The Falcon and the Snowman (1985) and starred in At Close Range (1986). After briefly stepping away from acting, he returned in State of Grace (1990).

Penn made his directorial debut with The Indian Runner (1991). He returned to acting in Carlito's Way (1993), earning a Golden Globe nomination.

He directed The Crossing Guard (1995) and starred in Dead Man Walking (1995), receiving his first Academy Award nomination. He won Best Actor at Cannes for She's So Lovely (1997) and also appeared in U Turn (1997), The Game (1997), Hurlyburly (1998), The Thin Red Line (1998), and Sweet and Lowdown (1999), earning another Oscar nomination.

In 2001, Penn starred in I Am Sam, earning his third Academy Award nomination. He won his first Oscar for Mystic River (2003). That same year, he appeared in 21 Grams. He directed Into the Wild, receiving a Directors Guild nomination. In 2008, he portrayed Harvey Milk in Milk, winning his second Academy Award for Best Actor. He later appeared in Fair Game, The Tree of Life, and This Must Be the Place.

Penn starred in The Gunman and directed The Last Face and Flag Day. In 2018, he led the Hulu series The First. He portrayed John N. Mitchell in the Starz series Gaslit and directed the documentary Superpower about Ukrainian President Volodymyr Zelenskyy. He appeared in Daddio and reunited with director Paul Thomas Anderson for One Battle After Another. He also appeared in the Ukrainian anthology film War Through the Eyes of Animals.