Sean Penn

Sean Penn is an Oscar-winning actor and filmmaker. Sean was born and raised in Los Angeles to actor and director Leo Penn and actress Eileen Ryan. He attended Santa Monica High School, where he was classmates with Emilio Estevez and Charlie Sheen. He briefly enrolled in college after graduating but dropped out to pursue acting.

Penn began his career with a small role on Little House on the Prairie in the ’70s before gaining attention in films like Taps (1981) and Fast Times at Ridgemont High (1982). His early work established him as a prominent screen presence, and by the late 1980s and 1990s, he became one of Hollywood’s most respected dramatic actors. He also moved behind the camera, making his directorial debut with The Indian Runner in 1991.

The actor is known for acclaimed performances in Dead Man Walking (1995), I Am Sam (2001), Mystic River (2003) and Milk (2008). He has been awarded the Oscar for Best Actor twice, first for his performance in Mystic River and later for his role in Milk. As a director, his films include The Crossing Guard (1995) and Into the Wild (2007). In 2025, he appeared in the Golden Globe-winning film One Battle After Another alongside Leonardo DiCaprio and Benicio Del Toro.

Penn has been married three times. He wed Madonna in 1985 and the pair divorced in 1989. He later married Robin Wright, with whom he shares two children, Dylan Frances (born in 1991) and Hopper Jack (born in 1993). The couple divorced in 2010. He later married actress Leila George in 2020, and the two divorced in 2022. He moved on with Nathalie Kelley in 2024.