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 Dylan Penn in Sean Penn and Dylan Penn Ask Each Other Anything (2021)

Sean Penn and Vito Schnabel in Before Night Falls (2000)

Sean Penn, Jonathan Gilbert, and Jimmy McNichol in Little House on the Prairie (1974)

Sean Penn and Jimmy McNichol in Little House on the Prairie (1974)

Sean Penn and Jonathan Gilbert in Little House on the Prairie (1974)

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)