Jude Law and Sean Penn at an event for All the King's Men (2006)

Sean Penn and Robin Wright at an event for The Interpreter (2005)

Sean Penn, Robin Wright, and Javier Bardem

Sean Penn and Robin Wright at an event for The Assassination of Richard Nixon (2004)

Sean Penn at an event for The Assassination of Richard Nixon (2004)

Tim Robbins, Billy Crystal, and Sean Penn

Tim Robbins, Charlize Theron, Renée Zellweger, and Sean Penn at an event for The 76th Annual Academy Awards (2004)

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

Sean Penn in Fast Times at Ridgemont High (1982)

Jennifer Jason Leigh, Sean Penn, Brian Backer, 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, 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)