At the 2026 Oscars, veteran Hollywood actor Sean Penn was among the big winners of the star-studded awards night. He bagged the Best Supporting Actor award for his impactful performance in One Battle After Another. This was his third acting Oscar win after Mystic River (2003) and Milk (2008). For this write-up, we have collated a list of the top five highest-grossing live-action films starring Sean Penn (in leading and key supporting roles), and where you can currently watch these movies online in the U.S.
1. One Battle After Another (2025)
- Director: Paul Thomas Anderson
- Worldwide Earnings: $210.6 million
- Streaming On: HBO Max
Plot: Inspired by Thomas Pynchon’s 1990 novel Vineland, the action-thriller follows Bob Ferguson (Leonardo DiCaprio), a former member of the revolutionary group French 75. His life is thrown into chaos when his daughter goes missing, and a dangerous enemy from his past resurfaces after sixteen years. The film stars Sean Penn, Benicio del Toro, Regina Hall, Teyana Taylor, and Chase Infiniti in pivotal roles.
2. The Secret Life of Walter Mitty (2013)
- Director: Ben Stiller
- Worldwide Earnings: $188.1 million
- Streaming On: Amazon Prime Video & Apple TV+ (Rent)
Plot: The adventure comedy-drama follows Walter Mitty (Ben Stiller), a shy employee at Life magazine. He escapes his routine life through daydreams. When an important negative goes missing, he steps out of his comfort zone and travels from Greenland to the Himalayas to find the legendary photographer (Sean Penn), but faces real dangers along the way.
3. The Interpreter (2005)
- Director: Sydney Pollack
- Worldwide Earnings: $162.9 million
- Streaming On: Amazon Prime Video & Apple TV+ (Rent)
Plot: The political thriller follows Silvia Broome (Nicole Kidman), a UN interpreter, who overhears a plot to assassinate an African head of state. A Secret Service agent (Sean Penn) begins to investigate the high-profile case and tries to uncover her past, and they both become involved in a political conspiracy.
4. Mystic River (2003)
- Director: Clint Eastwood
- Worldwide Earnings: $156.6 million
- Streaming On: Amazon Prime Video & Apple TV+ (Rent)
Plot: When Jimmy Markum’s (Sean Penn) teenage daughter is found murdered, the case shocks his Boston neighborhood. The police begin investigating the murder, and suspicion turns toward his childhood friend, Dave Boyle (Tim Robbins).
5. The Game (1997)
- Director: David Fincher
- Worldwide Earnings: $109.4 million
- Streaming On: Amazon Prime Video & Apple TV+ (Rent)
Plot: Wealthy investment banker Nicholas Van Orton is gifted a mysterious game by his brother for his 48th birthday. The experience quickly turns into a terrifying nightmare that begins to derail his life in unimaginable ways.
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