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- Shanghai Surprise (1986) In 1986 Sean Penn starred as Glendon Wasey, a fortune-hunter looking for a quick exit out of China, alongside his then-wife, Madonna, playing Gloria Tatlock, a nurse/missionary, in the notoriously terrible, "Shanghai Surprise."
- Crackers (1984) "Crackers" was a 1984 crime-comedy set in San Francisco with a promising cast including Sean Penn, Donald Sutherland, Jack Warden, and Trinidad Silva, but the film just didn't work.
- The Gunman (2015) In "The Gunman" Sean Penn plays Jim Terrier, an ex-special forces soldier and former assassin, who now works drilling wells after an assassination in the Congo forced him into hiding.
- Judgment in Berlin (1988) The 1988 film "Judgment in Berlin" is based on a true story of a group of people living in East Berlin who escaped to the West when two East Berliners hijack a plane in Poland.
- Mystic River. Sean Penn, Tim Robbins, Kevin Bacon. 131 votes. Mystic River showcases Sean Penn's powerful performance in a dramatic exploration of friendship, loss, and redemption.
- Fast Times at Ridgemont High. Sean Penn, Jennifer Jason Leigh, Judge Reinhold. 130 votes. Fast Times at Ridgemont High is a seminal coming-of-age comedy that introduced audiences to Sean Penn's comedic chops through his unforgettable portrayal of stoner Jeff Spicoli.
- Carlito's Way. Al Pacino, Sean Penn, Penelope Ann Miller. 105 votes. Carlito's Way sees Sean Penn step into the world of gritty crime dramas with his riveting portrayal of lawyer David Kleinfeld alongside Al Pacino in Brian De Palma's stylish gangster epic.
- Dead Man Walking. Susan Sarandon, Sean Penn, Robert Prosky. 108 votes. Sean Penn delivers a raw and poignant performance in Dead Man Walking, a gripping drama that explores the moral complexities surrounding capital punishment.
Sean Penn is an American actor known for his versatility and intense roles on film. He made his feature film debut in the crime drama Taps (1981). He earned attention for his role as the stoner teenager Jeff Spicoli in the coming of age comedy film Fast Times at Ridgemont High (1982). [1]
- Mystic River. "Mystic River" is a heartbreaking depiction of a tragedy at the heart of a seemingly normal small town, and one of the greatest American films of the 21st century.
- Dead Man Walking. Penn can't be defined by just one genre or archetype, and has experience playing goofballs, heroes, and villains alike. As a result of his range, he can generate empathy for all types of characters, even if they seem inherently unlikeable.
- 21 Grams. In the same year that he was showered with critical praise for his career-defining role in "Mystic River," Penn delivered another awards-worthy performance in Alejando Gonzales Inarritu's heartbreaking drama "21 Grams."
- Carlito's Way. Although he's one of the most famous leading men of his generation, Penn has no issues slipping into supporting character parts. Al Pacino's work in Brain De Palma's 1993 film "Carlito's Way," in which he plays mob boss Carlito Brigante, is one of his greatest performances.
- Liam Gaughan
- Senior Author
- 'The Professor and the Madman' (2019) The Professor and the Madman may have received overwhelmingly negative reviews upon its initial release, but a majority of its harshest critics seem to have overlooked the fascinating true story that the film was interested in telling.
- 'Gangster Squad' (2013) Sometimes, it’s best to just let Penn have fun and play an extremely exaggerated character. 2013’s Gangster Squad felt like a throwback to classic gangster films with its retro style of storytelling and 1930s setting.
- 'This Must Be the Place' (2011) The Young Pope and The Hand of God filmmaker Pablo Sorrentino has an unparalleled ability to examine the existential search for meaning that haunts those in positions of influence.
- 'Fair Game' (2010) Fair Game is based on a true story that has particular significance to today’s conversations about the nature of whistleblower protections and political accountability.
21 Grams is a 2003 American psychological thriller film directed by Alejandro González Iñárritu and written by Guillermo Arriaga [3] The film stars Sean Penn, Naomi Watts, Charlotte Gainsbourg, Danny Huston and Benicio Del Toro.
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Apr 24, 2022 · Over the years, the two-time Oscar winner has carved out a niche acting in dramas, ranging from biopics to war movies to crime films. Penn's silver screen success began in the early 1980s when he took on the iconic role of surfer burnout Jeff Spicoli in Fast Times at Ridgemont High.
