Sean Penn

Did You Know?

• Penn's older brother is musician Michael Penn; his younger brother, actor Chris Penn, died in 2006.
• He began making short films with childhood friends Emilio Estevez and Charlie Sheen.

Career

Penn appeared as an extra in a 1974 episode of Little House on the Prairie, directed by his father Leo. He debuted in the action-drama Taps (1981) as a military cadet and made his Broadway debut that year in Heartland. In 1982 he played surfer-stoner Jeff Spicoli in Fast Times at Ridgemont High, a role that helped popularize the word "dude." The drama Bad Boys (1983) earned him favorable reviews and launched his serious acting career. He returned to Broadway in Slab Boys (1983) with Kevin Bacon and Val Kilmer. In The Falcon and the Snowman (1985) he played Andrew Daulton Lee, a convicted spy; Penn later hired Lee as his personal assistant, believing in rehabilitation. He starred in the critically acclaimed At Close Range (1986). Dissatisfied with the industry, he stopped acting for a few years in the early 1990s to focus on directing.

Personal life

Penn was engaged to Elizabeth McGovern, his co-star in Racing with the Moon, and also dated Demi Moore and Susan Sarandon. He met Madonna on the set of her "Material Girl" music video in January 1985; they married on August 16, 1985, her 27th birthday. They starred in the poorly received Shanghai Surprise (1986), and Madonna dedicated her album True Blue (1986) to him. Their marriage was marked by Penn's violent outbursts against the press.

Madonna filed for divorce in December 1987 but withdrew it; she filed again in January 1989 and reportedly withdrew an assault complaint after an incident at their Malibu home. Madonna denied allegations in the book Madonna Unauthorized that Penn struck her, calling them false. In 1989 Penn began dating Robin Wright; their daughter Dylan Frances was born April 13, 1991, and son Hopper Jack on August 6, 1993. They separated in 1995, during which he developed a relationship with Jewel after seeing her on Late Night with Conan O'Brien.

He reconciled with Wright and married her on April 27, 1996. They filed for divorce in December 2007 but reconciled; Penn filed for legal separation in April 2009 but withdrew it. Wright filed for divorce on August 12, 2009, finalized July 22, 2010. He dated Charlize Theron from December 2013 to June 2015; Theron said they were never engaged.

Political views and activism

Penn visited Iraq from December 13–16, 2002 to protest the Bush administration's plans for a military strike. On June 10, 2005, he visited Iran as a journalist for the San Francisco Chronicle, attending a Friday prayer at Tehran University. After the 2004 film Team America: World Police depicted a puppet of him claiming Baathist Iraq was a utopia, Penn sent an angry letter to creators Trey Parker and Matt Stone, inviting them to tour Iraq and ending with "fuck you."

On January 7, 2006, he joined Norman Solomon and Cindy Sheehan at an "Out of Iraq Forum" in Sacramento. He received the Christopher Reeve First Amendment Award from the Creative Coalition on December 18, 2006. In August 2008 he attended a Ralph Nader super rally protesting third-party exclusion. In October 2008 he visited Cuba and interviewed President Raúl Castro.

In 2021 he denounced cancel culture as "ludicrous." On October 18, 2002, he placed a $56,000 advertisement in The Washington Post as an open letter to President George W. Bush, criticizing the planned attack on Iraq and the "deconstruction of civil liberties." Madonna praised his stance.

Acting credits and accolades

Penn has appeared in over 50 films. He won Academy Awards for Best Actor for Mystic River (2003) and Milk (2008), and Best Supporting Actor for One Battle After Another (2025). He was also nominated for Dead Man Walking (1995), Sweet and Lowdown (1999), and I Am Sam (2001). He received a Directors Guild of America nomination for directing Into the Wild (2007) and the Honorary César in 2015.