Sean Penn – Bio, Net Worth, Relationships, Affairs, Brother, Daughter, Family

Sean Penn is an American-born actor, filmmaker, 2-time Academy-award winner, political activist, and author. Having marked his acting debut as a child actor on the western series Little House on the Prairie, Penn featured in the 1981 film Taps. Afterward, the talented actor received critical acclaim for his roles in films like At Close Range (1986), State of Grace (1990), and Carlito’s Way (1993).

Sean Penn consolidated his status as a Hollywood leading man with his performance in Dead Man Walking (1995), for which he received his first Best Actor Academy Award nomination. Having received 2 more nominations for his roles in Sweet and Lowdown (1999) and I Am Sam (2001), Penn eventually won his first Academy Award for Best Actor for his work in the drama film Mystic River (2003). 5 years later, the talented actor earned his second Academy Award for Best Actor for his performance in the biopic Milk (2008).

Having marked his directorial debut in the 1991 crime drama The Indian Runner, Sean Penn has since recorded additional directing credits including the highly-acclaimed 2007 biopic Into the Wild. In addition to his Hollywood superstar status, Sean Penn is also involved in political and social activism.

Sean Penn’s Bio, Age

Sean Justin Penn was born on August 17, 1960, in Santa Monica, California to Hollywood actress Eileen Ryan (née Annucci) and actor-director Leo Penn. He had his high school education at Santa Monica High School. As a teenager, Sean Penn earned his first acting role as an extra on the western series Little House on the Prairie, on an episode directed by his father. He delved into film several years later with a role in the 1981 action-drama Taps. This was followed by lead roles in Fast Times at Ridgemont High (1982), Bad Boys (1983), The Falcon and the Snowman (1985), At Close Range (1986) among several other films.

Sean Penn received his first 3 Academy award nominations for his performance in the movies Dead Man Walking (1995), Sweet and Lowdown (1999) and I am Sam (2001). He eventually clinched his first Oscar for his role in Clint Eastwood‘s crime drama Mystic River (2003)Over the years, the talented actor has gained a reputation for portraying real-life characters including his Oscar-winning portrayal of real-life gay-rights activist and politician Harvey Milk in the biopic Milk (2008). Sean Penn has also served as director for several films and music videos. The multitalented Hollywood star released his first novel Bob Honey Who Just Do Stuff in March 2018.

Family, Brother

Sean Penn was born into a family of entertainers; actors, filmmakers, and musicians. His mother has Irish and Italian ancestry while his father was of Russian Jewish descent. His late father Leo Penn was an actor and director. His mother Eileen Ryan is a film and television actress.

He was raised alongside 2 brothers. His older brother, Michael Penn is a singer and a songwriter. The youngest of the Penn brothers, Chris is also an actor with several TV and film roles to his credit. However, Chris Penn died of heart disease in 2006 at the age of 40.

Relationships & Affairs

In addition to his accomplishments as a movie star, Sean Penn has also made headlines for a number of high-profile relationships. Throughout his long-running career, the Hollywood hunk has been romantically involved with some of Tinseltown’s favorite leading ladies. Penn’s first major relationship was with fellow Hollywood star, Elizabeth McGovern. The duo got together in 1984 after meeting on the set of the film Racing with the Moon. The couple later announced their engagement, however, they never made it all the way to the altar.

The year after his first engagement, the Hollywood hunk met music royalty, Madonna. Things went pretty fast between these two as they got married on August 16, 1985, a few months after their first meeting. The lovestruck couple also co-starred in the 1986 adventure comedy film Shanghai Surprise. However, Penn’s 4-year marriage to Madonna was marred by several controversies including violent outbursts against the paparazzi as well as allegations of domestic violence.

Madonna first filed for divorce in December 1987 but she later withdrew it. She eventually filed again for divorce in January 1989 and it was finalized on September 14, 1989. 25 years after their not-so-amicable divorce, Madonna confirmed in an interview that all her claims of assault against Sean Penn were false.

Sean Penn’s longest relationship yet is that with Hollywood actress and director Robin Wright, the mother of his children. The couple moved in together after Penn’s first marriage came to an end. Their union produced two children – a daughter, Dylan Frances born in April 1991, and a son named Hopper Jack, born in August 1993.

Sean Penn and Robin Wright got separated in 1995 and during that hiatus, Penn had a brief romance with music artist, Jewel. The following year, Penn and Wright got back together and eventually tied the knot on April 27, 1996. Their marriage lasted for 14 years ending in divorce in July 2010.

Sean Penn apparently took some time off the dating scene after the end of his marriage. In 2013, he got together with Hollywood star Charlize Theron. They got engaged in December 2014, however, the relationship ended 6 months later.

In 2016, Sean Penn was linked with up-and-coming Hollywood actress Leila George D’Onofrio, daughter of Holywood actor-producer Vincent D’Onofrio. With a 31-year age difference between them, Sean Penn and Leila George proved that age is indeed just a number.


Sean Penn’s first daughter Dylan Frances Penn was born on April 13, 1991, during his marriage to fellow actor and director Robin Wright. Having inherited a large pool of genes for showbiz, it comes as no surprise that Dylan Penn has towed the path of her highly talented parents. She currently works as a model and actress.

The young Penn scored her first major modeling gig in 2013 when she appeared in ads for Gap. She has also been featured in GQ, W, Elle, and Treats! magazines. As an actress, her earlier movie features include the horror-comedy Condemned (2015) and the comedy-drama Elvis & Nixon (2016).

Net Worth

Sean Penn’s illustrious Hollywood career currently spans about 4 decades. He has equally remained consistent both as an actor and a director. His career earnings coupled with numerous juicy endorsement deals bring the net worth of the movie star to an estimate of $150 million.

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