Sean Penn's Early Life
Sean Justin Penn was born on August 17, 1960 in Santa Monica, California to actor and director Leo Penn and actress Eileen Ryan. His older brother, Michael, is a musician and his younger brother, Chris (d. 2006), was an actor as well.
He grew up making short films with childhood friends Emilio Estevez and Charlie Sheen and made his onscreen debut as an extra on a 1974 episode of Little House on the Prairie, which his father directed. His first role as an adult was in 1981's Taps opposite Timothy Hutton, George C. Scott, and Tom Cruise.
Sean Penn's Rise to Fame and Career
Penn made waves with performances in Fast Times at Ridgemont High (1982), Bad Boys (1983), and At Close Range (1986), before taking time off acting to make his directorial debut with 1991's The Indian Runner. He returned with three performances that netted him Academy Award nominations: Dead Man Walking (1995), Sweet and Lowdown (1999), and I am Sam (2001).
He won on his fourth nomination in 2003 for Mystic River and followed that up with another Oscar win in 2008 for Milk. His other notable performances since then include 2010's Fair Game, 2011's The Tree of Life, and 2021's Licorice Pizza, which was nominated for a Best Picture Oscar.
Sean Penn's Personal Life
Penn's personal life has been the subject of much controversy, mired with legal issues and turbulent marriages. He was engaged to Elizabeth McGovern before meeting Madonna in 1985. They married later that year before Madonna filed for divorce in 1987, withdrew the papers, and filed for good once again in 1989, with Penn's often violent outbursts toward the media cited as a reason why.
He soon began dating Robin Wright, welcoming children Dylan Frances (b. 1991) and Hopper Jack (b. 1993) before they split up in 1995 and he began a relationship with singer Jewel. They rekindled their romance in 1996 and tied the knot, before filing for divorce in 2007. They reconciled and withdrew the case before filing again in April 2009, reconciling once again, and then finally filing that August. Their divorce was finalized in 2010.
He dated Charlize Theron from 2013-2015 before beginning a relationship with Australian actress Leila George in 2016. They were married in 2020, but filed for divorce a little over a year later. Their divorce was finalized in April 2022.
Penn is also well known for his political activism, and was extremely outspoken against the George W. Bush administration. He was involved in several foreign visits and humanitarian efforts, most notably in the aftermath of Hurricane Katrina and 2010's Haiti Earthquake.
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