In 1974, Penn appeared in an episode of the television series ‘Little House on the Prairie’ which had a few episodes directed by his father.
He made his film debut with the movie ‘Taps’ in 1981. The following year, he appeared in the successful comedy film ‘Fast Times at Ridgemont High.’
In 1983, he played the character of a troubled youth in ‘Bad Boys,’ winning appreciation for his acting skills.
In 1985, Penn was seen in ‘The Falcon and the Snowman.’ The next year, he appeared in the drama film ‘At Close Range,’ which featured Madonna’s single, ‘Live to Tell.’
He took a break from his acting career to work as a director during the early-1990s. His first film as a director was ‘The Indian Runner’ which released in 1991.
Coming back from a hiatus, he appeared in films, such as ‘The Last Party’ and ‘Carlito’s Way’ in 1993. Two years later, he was seen in ‘Dead Man Walking.’ The same year, he worked as a director in ‘The Crossing Guard.’
The year 1997 was a productive one for Penn. He was seen in several movies like ‘Loved,’ ‘She’s So Lovely,’ ‘U Turn,’ ‘The Game,’ and ‘Hugo Pool.’
For his portrayal of ‘Emmett Ray’ in Woody Allen’s ‘Sweet and Lowdown’ in 1999, he received an ‘Academy Award’ nomination. He was also seen in a small role in ‘Being John Malkovich.’
His next film ‘I am Sam’ was released in 2001 and his work in the film received immense critical appreciation. His third directorial venture ‘The Pledge’ released the same year.
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In 2003, he appeared in ‘Mystic River’ which was directed by Clint Eastwood. Penn won an ‘Academy Award’ for his work in the film. He was also seen in the movie ‘21 Grams.’
He was seen in ‘The Assassination of Richard Nixon’ in 2004. The same year, he was invited to be a member of the ‘Academy of Motion Picture Arts and Sciences.’
Two years later in 2006, he played ‘Governor Willie Stark’ in the film adaptation of the novel ‘All the King’s Men.’ The film was a commercial failure and received negative reviews from the critics.
In 2007, his directorial movie ‘Into the Wild’ was released. The film received a lot of appreciation from the critics, and the film’s music became popular.
Penn won another ‘Academy Award’ for his impeccable portrayal of gay icon Harvey Milk in the biopic ‘Milk’ (2008). He received praises for his work, and also won several other awards.
In 2010, he worked in ‘Fair Game.’ The following year, he was seen in ‘The Tree of Life’ which won him awards at the ‘Cannes Film Festival.’
In 2013, he worked in movies, such as ‘Gangster Squad’ and ‘The Secret Life of Walter Willy.’
In 2015, he was seen in the action thriller film ‘The Gunman.’ He also voiced a character in the 2016 animated film ‘The Angry Birds Movie.’
‘Atria Books’ published Penn's novel ‘Bob Honey Who Just Do Stuff’ on March 2018. In 2019, he played the role of ‘Dr. William Chester Minor’ in the biographical drama film ‘The Professor and the Madman.’
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After a string of movies, which won him nominations at various award ceremonies, Penn finally won the ‘Academy Award’ for his role in the movie ‘Mystic River.’ The film received great critical appreciation and garnered $156,822,020 at the box office.
‘Milk’ was one of his most significant works and established him as a bankable actor. The movie also won him several awards, including the ‘Academy Award’ for ‘Best Actor.’
Personal Life & Legacy
Penn was engaged to Elizabeth McGovern. However, he went on to marry Madonna in 1985. After being charged for domestic violence, the couple divorced in 1989.
He dated actor Robin Wright—and the couple had two children, a daughter named Dylan Frances and a son named Hopper Jack—before getting married in 1996. The couple divorced in 2010.
Penn began dating actor Charlize Theron on December 2013. The two had announced their engagement on December 2014. However, Theron ended their relationship on June 2015.