Sean Penn

Not content with being one of the finest actors around, Hollywood's bad boy is fast becoming a hot director. From popstar marriages to 'I Am Sam', Penn's presence never fails to impress.


Sean Justin Penn was born to Leo Penn, an actor and director, and Eileen, an actress. Penn's father was the son of Jewish immigrants from Lithuania and Russia. The Penn surname was originally Piñon, but was changed when Penn's grandfather immigrated to the United States.

Penn’s first ten years were spent in different parts of California's San Fernando Valley, before moving to Malibu, where he attended Santa Monica High School. His schoolmates included fellow actors Emilio Estevez, Charlie Sheen and Rob Lowe.

Penn’s interest in film-making began at an early age, most likely due to his parent’s influence (Penn’s father was a major TV director throughout the Sixties to Eighties, helming episodes of 'Star Trek', 'Columbo' and 'Starsky And Hutch' among many more) and he skipped college to spend two years with the Los Angeles Repertory Company where he worked backstage, cleaning, carrying and gradually learning to act. Here Penn directed a one-act play called 'Terrible Jim Fitch' and also studied under the legendary acting coach Peggy Feury.

He made his screen debut in 1974 appearing alongside his mother in 'The Little House Of The Prairie'. By 1979, he made his professional debut in an episode of 'Barnaby Jones' directed by his father. Leo was responsible for Penn’s TV movie debut, 'Hellinger's Law', an unsuccessful pilot starring Telly Savalas.

It was as part of the hyped ‘brat pack’ that Penn truly first made his mark. In 1981, he played the title role in the TV movie 'The Killing Of Randy Webster' which also starred Jennifer Jason Leigh and Anthony Edwards. Next came 'Taps' alongside the then unknown Tom Cruise and soon there was a faint buzz in Hollywood that Penn could soon be the next big star.

After Taps came 'Fast Times At Ridgemont High' (1982) which was Penn’s first prominent role, likewise for writer Cameron Crowe. 'Bad Boys' in 1983 saw him playing a child sent to an offender’s institute for accidentally killing a man. It was this film where Penn’s habit for intense role-research began, when he spent time with the gang-crimes unit of the Chicago police.

Penn preferred to seek out the more unusual roles, shying away from typical Brat Pack comedies and examples of this came with 'Racing With The Moon' (1984) alongside Nicholas Cage and 'The Falcon And The Snowman' (1985).

1985 was a significant point in Penn’s life, not thanks to his acting talents but due to his relationship with Madonna who he’d met on the video shoot of her single Material Girl when invited along by his friend and its director, Mary Lambert.

For the next four years the press was hungry for snaps and gossip on the pair - they were the hottest new couple on the Hollywood and music scene. Penn hated the attention though and regularly took out his frustrations on photographers who happened to get in his way. Despite this he proposed to Madonna and by August 1985, they were married in a ceremony in Nashville where Penn famously was so enraged by the media’s scrum to get their noses in on the action he shot at helicopters circling overhead.


Prior to the release of 'At Close Range' in 1986 (which Penn starred in with his mother and brother Chris), there came the furor as Penn and Madonna were hounded by the press during the filming of 'Shanghai Surprise'. After a photographer from The Sun was knocked over by Penn's car, the tabloids were in uproar and it grew so out of control that producer George Harrison called a press conference to calm things down. The press didn’t forget though and unsurprisingly, the reviews of the film were vicious.

By 1987, Penn and Madonna’s marriage was severely on the rocks - heightened by Penn being jailed for 32 days for assaulting an extra, who was taking photos without permission. In December 1987, Madonna filed for divorce, changed her mind a week later but in January 1989, she filed again and this time moved into a new house. The end of the marriage ironically saw both Madonna and Penn peak in their careers. Madonna released one of her finest and most controversial singles, Like A Prayer, while Penn went on to appear in a number of successful films.

After low-key hits such as Dennis Hopper's 'Colours' and 'Judgment In Berlin' (directed by his father) in 1988, he started to attract greater critical and audience acclaim in 1989 with 'Casualties Of War' and then 'State Of Grace' in 1990 alongside Ed Harris and Gary Oldman.

1990 was a turning point in Penn’s personal and working life when he began a relationship with Robin Wright who he’d met while filming 'State of Grace'. Within six years the couple lived together and went on to have two children - daughter Dylan Frances and son Hopper Jack (named respectively after Dennis Hopper and Jack Nicholson) - before getting married in 1996.

Penn at this time also decided to retire from acting and turned to writing and directing with 'The Indian Runner' but with the acting bug in his genes, he couldn't stay away for long. Thankfully for his fans and critics alike Penn did return to this big screen and this time in a major role in the 1993 blockbuster, 'Carlito's Way'. He finally received the industry recognition he deserved in being nominated for a Golden Globe for Best Performance by an Actor in a Supporting Role.

Yet Tim Robbins' 'Dead Man Walking' (1995) is often seen as Penn’s most pivotal role. Starring as Matthew Poncelet, a prisoner on Death Row who's befriended by nun Helen Prejean played by Susan Sarandon, the film was based on a true story and it earned Sarandon a Best Actress Oscar while Penn was also nominated as Best Actor. 'She's So Lovely' (1997) saw husband and wife reunited on screen and off as Penn played the wayward drunken husband of Robin Wright who eventually marries the ‘good guy’ in the guise of John Travolta.


'She's So Lovely' was followed the same year by two big budget films 'U-Turn' and 'The Game', setting the seal on Penn's future working agenda of being able to switch between large and small projects. 'The Thin Red Line' marked a more ‘Hollywood’ inclined hit for Penn with a successful release in 1998, after which he continued to direct, making 'The Crossing Guard' with Jack Nicholson, Angelica Huston and his wife Robin once again.

As well as Penn’s typical ‘low-key’ ventures ('Before Night Falls' and 'The Weight Of Water' in 2000), he took on two more prime roles which would impress a universal audience. First he starred as a drunk but brilliant jazz guitarist in Woody Allen's 'Sweet And Lowdown' which earned him another Oscar nomination. Then followed, 'I Am Sam', playing a completely opposing character as an adult with a mental age of seven alongside Michelle Pfeiffer, for which Penn was also Oscar nominated.

Penn’s next series of performances would catagorise him as exceptional, even beyond his own hefty expectations as an actor. 2004 brought Clint Eastwood's 'Mystic River' where he, Kevin Bacon and Tim Robbins played three childhood friends scarred by an abduction and molestation. As adults, they are reunited by the murder of shopkeeper Penn's daughter, a crime to be investigated by cop Bacon, with Robbins, who returned to his house covered in blood on the night of the murder, as one of the chief suspects. Penn deservedly won a Golden Globe and an Oscar as Best Actor in a Leading Role Oscar, surprisingly turning up to accept the latter after years of refusing to attend the ceremony.

Further critical acclaim would follow with '21 Grams', with Penn taking the role of a maths professor dying from a heart condition and being pestered by wife Charlotte Gainsbourg into donating sperm so she can have his baby. As the Academy rarely nominated an actor twice, his outstanding performance went un-recognised, yet the British Academy would nominate him for both 'Mystic River' and '21 Grams' in the same year.

In 2004, 'The Assassination Of Richard Nixon' told the true-life tale of Samuel Byck who, in February 1974, failed in an attempt to kill the President and Penn once again gave a star turn, impressing both critics and audiences nationwide alike. Next Penn has starred in two more ‘big-budget’ films, 'The Interpreter' in 2005 and 'All The King’s Men' in 2006, both of which only sought to add to his credentials as one of Hollywood’s most talented actor and directors.

His latest roles include 'Milk' (2008), for which he won an Oscar for Best Actor, Gangster Squad (2013) and 'The Gunman' (2014).

Penn divorced from Robin Wright-Penn in 2010. He is currently dating Charlize Theron.