Sean Penn

Sean Penn (born August 17, 1960, Santa Monica, California, U.S.) is an American actor and director known for his wide-ranging and intense performances. He has twice won the Academy Award for best actor, for Mystic River (2003) and Milk (2008).

Early career, Fast Times at Ridgemont High, and marriage to Madonna

The son of show-business parents, Penn chose to forgo college and instead joined the Los Angeles Repertory Theater. After a few television appearances, including a role in an episode of Barnaby Jones (1979), he moved to New York City in 1980. Well-received performances in the Off-Broadway Heartlands and the film Taps (both 1981) paved the way for Penn’s fame-making role as the underachieving surfer Jeff Spicoli in Fast Times at Ridgemont High (1982).

He followed with a variety of roles that showcased his intensity and versatility—including as a teenage delinquent in Bad Boys (1983), a punk rocker-burglar in Crackers (1984), a World War II marine about to ship out in the romance Racing with the Moon (1984), and a spy selling U.S. government secrets to the KGB in The Falcon and the Snowman (1985)—garnering favorable notices from critics even when the vehicle he performed in was not as well liked. Penn’s career took a downturn, however, during his relationship with pop star Madonna, whom he married in 1985. There were frequent confrontations with paparazzi, a number of them combative, and Penn spent a month in jail in 1987. The marriage ended in 1989, but not before the couple had costarred in Shanghai Surprise (1986), a film reviled by most critics.

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Dead Man Walking, I Am Sam, and Mystic River

Penn’s subsequent movies did better, however, and he also branched out, writing and directing Indian Runner (1991) and directing The Crossing Guard (1995). He earned his first Academy Award nomination for Dead Man Walking (1995), starring opposite Susan Sarandon as a death-row inmate. He appeared with his second wife—Robin Wright (married 1996; divorced 2010)—in She’s So Lovely (1997), for which he was named best actor at the Cannes film festival. In 1998 he starred in Terrence Malick’s World War II drama The Thin Red Line, and he later received Oscar nominations for Sweet and Lowdown (1999) and I Am Sam (2001).

Another impressive directorial effort came with The Pledge. The 2001 drama featured Jack Nicholson as a police detective who vows to find a child killer. In 2003 Penn won best actor honors at the Venice Film Festival for 21 Grams (2003), and the following year he received a best actor Oscar for his role as the grief-stricken father of a murdered young woman in Mystic River (2003).

Into the Wild, Milk, and Fair Game

Penn’s subsequent films during this period include The Assassination of Richard Nixon (2004), based on an actual attempt on the president’s life; The Interpreter (2005); and All the King’s Men (2006), an adaptation of Robert Penn Warren’s novel about a populist politician. Penn returned to directing with Into the Wild (2007). The film—based on Jon Krakauer’s best-selling book of the same name—chronicles the journey of Christopher McCandless, an idealistic college graduate who repudiates materialistic society as he hitchhikes through the American West and ventures alone into the Alaskan wilderness.

In 2008 Penn played the lead role in Milk, which depicts the life of Harvey Milk, one of the first openly gay elected officials in the United States. His ebullient portrayal of Milk earned him a second Academy Award for best actor. Penn played another real-life figure, retired U.S. diplomat Joseph C. Wilson, in Fair Game (2010). The thriller was based on the 2003 scandal in which White House officials leaked the identity of Wilson’s wife—Valerie Plame, a covert CIA agent—in an alleged attempt to discredit his criticism of the U.S.-led Iraq War.

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Later work

In Malick’s impressionistic drama The Tree of Life (2011), Penn appeared as a man haunted by memories of his childhood. Penn later portrayed a former rock star turned Nazi hunter in This Must Be the Place (2011), mid-20th-century mob boss Mickey Cohen in the noir drama Gangster Squad (2013), and a reformed assassin whose past catches up with him in The Gunman (2015). Penn also occasionally voiced characters in animated fare, including Persepolis (2007) and Angry Birds (2016).

He starred as a seasoned astronaut in the TV series The First (2018), a fictional account of the pioneer manned mission to Mars; it was canceled after one season. Penn returned to the big screen in The Professor and the Madman (2019), about the early compilation of The Oxford English Dictionary. In 2020 Penn married Leila George, the daughter of actor Vincent D’Onofrio; the couple divorced in 2022.

In 2021 Penn directed and starred in the drama Flag Day, in which a young woman (played by his daughter, Dylan Penn) discovers her father’s criminal past. Later that year he appeared in Paul Thomas Anderson’s coming-of-age dramedy Licorice Pizza. In the TV miniseries Gaslit (2022), Penn portrayed U.S. Attorney General John Mitchell, who was involved in the Watergate scandal. Penn again worked with Anderson on One Battle After Another (2025), an action epic in which Penn played Col. Steven J. Lockjaw, the antagonist of a former revolutionary (played by Leonardo DiCaprio).

Activism and other activities

Penn is a political activist, and he often attracted controversy for his stances, most notably his opposition to the Iraq War, his criticism of U.S. Pres. George W. Bush, and his support for Venezuelan Pres. Hugo Chávez. He participated in the recovery efforts in New Orleans after Hurricane Katrina (2005) and in Haiti after the devastating 2010 earthquake. He traveled to Ukraine several times during that country’s war with Russia and codirected the documentary Superpower (2023), which features interviews with Ukrainian Pres. Volodymyr Zelensky and other Ukrainians.

In 2018 Penn published his first novel, Bob Honey Who Just Do Stuff, a satire about a divorced assassin. A sequel, Bob Honey Sings Jimmy Crack Corn, appeared the following year.