“I ain’t no punk, man.”
— Bad Boys (1983)
From gritty dramas to heartfelt character studies, Sean Penn’s intense performances have made him one of cinema’s most respected actors. Here’s the full list — which three make your cut?
- 21 Grams (2003) – A gripping tale of loss, fate, and redemption.
- All the King’s Men (2006) – Political drama about power and corruption.
- Asphalt City (2024) – Crime drama set against a gritty urban backdrop.
- At Close Range (1986) – A tense family crime drama with Christopher Walken.
- Bad Boys (1983) – Juvenile detention drama that cemented Penn’s early stardom.
- Before Night Falls (2000) – Biographical drama about Cuban poet Reinaldo Arenas.
- Being John Malkovich (1999) – Surreal comedy about a portal into a celebrity’s mind.
- Carlito’s Way (1993) – Al Pacino crime thriller with Penn as a sleazy lawyer.
- Casualties of War (1989) – Harrowing Vietnam War drama based on true events.
- Colors (1988) – LAPD officers navigate gang conflicts in Los Angeles.
- Crackers (1984) – Comedy about a group of bumbling burglars.
- Daddio (2024) – Two strangers connect during a taxi ride in New York.
- Dead Man Walking (1995) – A powerful death row drama with Susan Sarandon.
- Fair Game (2010) – Political thriller about CIA operative Valerie Plame.
- Fast Times at Ridgemont High (1982) – Iconic teen comedy featuring surfer Spicoli.
- Fast Times at Ridgemont High: A Virtual Table Read (2020) – Reunion charity event revisiting the classic.
- Flag Day (2021) – Family drama directed by Penn himself.
- Gangster Squad (2013) – Stylish crime action set in 1940s Los Angeles.
- Hugo Pool (1997) – Offbeat romantic comedy with a quirky twist.
- Hurlyburly (1998) – Dark Hollywood satire about broken lives.
- I Am Sam (2001) – Heartwarming drama about a father fighting for custody.
- I’m Still Here (2010) – Mockumentary chronicling Joaquin Phoenix’s “retirement.”
- It’s All About Love (2003) – Surreal romance set in a dystopian world.
- Judgment in Berlin (1988) – Courtroom drama set during the Cold War.
- Licorice Pizza (2021) – Paul Thomas Anderson’s nostalgic coming-of-age tale.
- Milk (2008) – Oscar-winning portrayal of activist Harvey Milk.
- Mystic River (2003) – Clint Eastwood’s crime drama that earned Penn an Oscar.
- Racing with the Moon (1984) – Small-town romance set during WWII.
- Risky Business (1983) – Tom Cruise’s breakout hit featuring a Penn cameo.
- She’s So Lovely (1997) – Intense romance with John Travolta and Robin Wright.
- State of Grace (1990) – Undercover cop thriller in New York’s Irish mob.
- Summerspell (1983) – Small-town Texas family drama.
- Sweet and Lowdown (1999) – Woody Allen’s story of a fictional jazz guitarist.
- Taps (1981) – Military academy cadets rebel in this early role for Penn.
- The Angry Birds Movie (2016) – Voice role in the animated hit.
- The Assassination of Richard Nixon (2004) – True story of a man pushed to extremes.
- The Falcon and the Snowman (1985) – Espionage thriller about two unlikely spies.
- The Game (1997) – Psychological thriller starring Michael Douglas.
- The Gunman (2015) – Action-thriller with Penn as a former assassin.
- The Interpreter (2005) – Political thriller set inside the UN.
- The Professor and the Madman (2019) – Story of the creation of the Oxford English Dictionary.
- The Secret Life of Walter Mitty (2013) – Penn plays a mysterious photographer.
- The Thin Red Line (1998) – Terrence Malick’s poetic WWII epic.
- The Tree of Life (2011) – Philosophical drama about memory and existence.
- The Weight of Water (2000) – Mystery spanning two centuries.
- This Must Be the Place (2011) – An aging rock star searches for a Nazi war criminal.
- U Turn (1997) – Oliver Stone’s twisted neo-noir thriller.
- Up at the Villa (2000) – Romantic intrigue set in pre-WWII Italy.
- We’re No Angels (1989) – Two escaped convicts hide out as priests.
- What Just Happened (2008) – Hollywood satire starring Penn as himself.