Sean Penn in Fast Times at Ridgemont High (1982)

Jennifer Jason Leigh, Sean Penn, Brian Backer, Kelli Maroney, and Scott Thomson in Fast Times at Ridgemont High (1982)

Sean Penn and Amanda Wyss in Fast Times at Ridgemont High (1982)

Sean Penn, Eric Stoltz, and Stanley Davis Jr. in Fast Times at Ridgemont High (1982)

Sean Penn and Stanley Davis Jr. in Fast Times at Ridgemont High (1982)

Sean Penn and Ray Walston in Fast Times at Ridgemont High (1982)

Jennifer Jason Leigh, Sean Penn, Taylor Negron, and Amanda Wyss in Fast Times at Ridgemont High (1982)

Sean Penn, Forest Whitaker, and Stanley Davis Jr. in Fast Times at Ridgemont High (1982)

Sean Penn and Alana Haim in Licorice Pizza (2021)

Sean Penn, Volodymyr Zelenskyy, and Andrii Yermak in Superpower (2023)

Julia Roberts and Sean Penn in Gaslit (2022)

Sean Penn and Chris Penn in At Close Range (1986)

Sean Penn and Jennifer Runyon in The Falcon and the Snowman (1985)

Sean Penn in One Battle After Another (2025)

Sean Penn and Teyana Taylor in One Battle After Another (2025)

Anthony Edwards, Sean Penn, Eric Stoltz, and Judge Reinhold in Fast Times at Ridgemont High (1982)

Sean Penn, Martin Sheen, and Sam Wanamaker in Judgment in Berlin (1988)

Nicole Kidman and Sean Penn in The Interpreter (2005)

Tom Cruise, Timothy Hutton, and Sean Penn in Taps (1981)

Sean Penn, Benicio Del Toro, and Naomi Watts in 21 Grams (2003)

Anthony Hopkins, Jude Law, Sean Penn, and Kate Winslet in All the King's Men (2006)

Madonna and Sean Penn in Shanghai Surprise (1986)