Two-time Oscar winner Sean Penn has excelled in a number of fields, including acting, writing and directing. But it’s his career as a performer that has brought him the most acclaim. Let’s take a look back at 15 of his greatest films as an actor, ranked worst to best.
Penn entered the Oscar race for the first time with his performance as a death row inmate in Tim Robbins’s “Dead Man Walking” (1995), for which he competed in Best Actor. Subsequent lead nominations as a jazz guitarist in Woody Allen’s “Sweet and Lowdown” (1999) and a mentally handicapped father in “I Am Sam” (2001) quickly followed.
He hit the Oscar jackpot with Clint Eastwood’s “Mystic River” (2003), which cast him as a criminal grieving the murder of his daughter. Just five years later, he returned to the winner’s circle with his lead role in “Milk” (2008), Gus Van Sant’s biopic about slain LGBTQ civil rights leader and politician Harvey Milk.
Penn has also had a successful directorial career, stepping behind the camera for the first time with “The Indian Runner” (1991) and subsequently helming “The Crossing Guard” (1994), “The Pledge” (2001) and “The Last Face” (2016). He achieved his greatest success with the critically acclaimed adaptation of “Into the Wild” (2007), for which he earned DGA and Critics Choice nominations in Best Director, plus WGA and Critics’ Choice bid for screenwriting.
In addition to his Oscar success, Penn also won a Golden Globe for “Mystic River” and a SAG prize for “Milk.”
Tour our photo gallery of Penn’s greatest films, including some of the titles listed above, as well as “Fast Times at Ridgemont High” (1982), “At Close Range” (1986), “The Thin Red Line” (1998) and more.
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15. I AM SAM (2001)
Image Credit: Lorey Sebastian/New Line/Kobal/Shutterstock Directed by Jessie Nelson. Written by Kristine Johnson and Jessie Nelson. Starring Sean Penn, Michelle Pfeiffer, Dianne Wiest, Dakota Fanning, Richard Schiff, Loretta Devine, Laura Dern.
Saccharine and manipulative in the extreme, “I Am Sam” tries to convince audiences that a grown man with the intelligence of a seven-year-old (Penn) is capable of caring for his young daughter (Dakota Fanning) purely through the power of love. It’s an argument that makes no logical sense, and the so-called “bad guys” — i.e. Child Protective Services — do nothing to dissuade this opinion. Yet the film nevertheless goes full bore, trying its darndest to pull at our heartstrings with every trick in the bag. Penn does manage to rise above the material in a role that brought him an Oscar nomination as Best Actor.
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14. THE GAME (1997)
Image Credit: Polygram/Kobal/Shutterstock Directed by David Fincher. Written by John Brancato and Michael Ferris. Starring Michael Douglas, Sean Penn, James Rebhorn, Deborah Kara Unger, Peter Donat, Carroll Baker, Armin Mueller-Stahl.
Though David Fincher’s psychological thriller belongs to Michael Douglas, Penn nearly steals the show away from him in some choice scenes. “The Game” concerns an extremely wealthy banker (Douglas) whose estranged younger brother (Penn) gives him a very special gift for his birthday: he’s given the opportunity to participate in a mysterious game that turns out to be a physical and mental endurance test that could cost him dearly. Filled with more twists and turns than a pretzel, this is a film noir masterpiece about the thread our lives hang on. Both Douglas and Penn are exceptional as the emotionally distant siblings.
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13. THE ASSASSINATION OF RICHARD NIXON (2004)
Image Credit: Phil Bray/Anhelo Prods/Kobal/Shutterstock Directed by Niels Mueller. Written by Niels Mueller and Kevin Kennedy. Starring Sean Penn, Don Cheadle, Jack Thompson, Naomi Watts, Brad William Henke, Michael Wincott, Mykelti Williamson.
One of the most underrated entries in Penn’s filmography, “The Assassination of Richard Nixon” is a haunting and disturbing portrait of isolation and delusion. Based on a true story, it centers on Sam Byck (renamed “Bicke” here), a woefully inept insurance salesman reeling from the divorce from his wife (Naomi Watts) and his failed business ventures. As his life continues to spiral out of control, he becomes increasingly obsessed with President Richard Nixon, who he views as history’s greatest salesman. His rage turns violent and deadly when he hatches a desperate scheme to get his life back on track.
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12. FAIR GAME (2010)
Image Credit: Moviestore/Shutterstock Directed by Doug Liman. Screenplay by Jez Butterworth and John Butterworth, based on the books ‘Fair Game’ by Valerie Plame and ‘The Politics of Truth’ by Joseph C. Wilson. Starring Naomi Watts, San Penn, Noah Emmerich, Ty Burrell, Sam Shepard, Bruce McGill, Khaled El Nabawy, Liraz Charhi.
Doug Liman’s “Fair Game” tells a true story with all the suspense and drama of a first-rate espionage thriller. Set in 2003, it stars Naomi Watts as Valerie Plame, a CIA operative whose identity was allegedly leaked by the U.S. government in retaliation for an op-ed written by her husband, Joseph Wilson (Penn), criticizing the Bush administration’s march towards war in Iraq. Though it’s far from an historically accurate docudrama, it’s still a powerful condemnation of the way our democracy can treat its most vocal dissenters. It’s a shame the film didn’t do better at the box office, because Penn and Watts are both truly Oscar worthy.
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11. THE TREE OF LIFE (2011)
Image Credit: Cottonwood/Kobal/Shutterstock Written and directed by Terrence Malick. Starring Brad Pitt, Sean Penn, Jessica Chastain, Hunter McCracken.
Terrence Malick’s “The Tree of Life” is feat of filmmaking unlike any other, an encapsulation of worldly existence beginning at the dawn of time and ending in the afterlife. In between is the story of three young boys coming of age in 1950s Texas, with a domineering father (Brad Pitt) and a loving mother (Jessica Chastain) representing the epic struggle between nature and grace. Penn plays the eldest son, Jack, as an adult haunted by the death of his brother, trying to reconnect with his parents after years harboring old wounds. A Palme d’Or-winning masterpiece that’s unlike anything you’ve ever seen before or since.
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10. THE FALCON AND THE SNOWMAN (1985)
Image Credit: Moviestore/Shutterstock Directed by John Schlesigner. Screenplay by Steven Zaillian, based on the book by Robert Lindsey. Starring Timothy Hutton, Sean Penn, Pat Hingle, Joyce Van Patten, Richard Dysart, Priscilla Pointer.
“The Falcon and the Snowman” concerns one of those truth-is-stranger-than-fiction stories that’s almost too bizarre to be believed, grounded in reality by director John Schlesinger and stars Timothy Hutton and Sean Penn. Hutton stars as Christopher Boyce, a young defense contractor whose best friend, Andrew Daulton Lee (Penn), is a cocaine dealer. Almost by accident, the two become involved with the Soviet Union, eventually selling secrets to the enemy at the height of the Cold War. Penn is mesmerizing as Lee, a desperate drifter angered by the direction his life has taken and hoping for a change, which proves his downfall.
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9. CARLITO’S WAY (1993)
Image Credit: Snap/Shutterstock Directed by Brian De Palma. Written by David Koepp, based on the books “Carlito’s Way” and “After Hours” by Edwin Torres. Starring Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo, Luis Guzman, Viggo Mortensen.
A sort of spiritual sequel to “Scarface,” “Carlito’s Way” casts Al Pacino as a Puerto Rican ex-con trying to start life anew on the outside. He pledges to stay out of drugs and crime, even starting a romance with a beautiful ballet dancer (Penelope Anne Miller). But he gets pulled back into the muck thanks to his boneheaded lawyer (Penn). Though lacking the campiness and raw power of Brian De Palma’s previous mob epic, “Carlito’s Way” is still a stylish, entertaining thriller with a killer climax set in NYC’s Penn Station. Penn is particularly good in an unrecognizable role that brought him a Golden Globe bid as Best Supporting Actor.
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8. 21 GRAMS (2003)
Image Credit: Jim Sheldon/Focus Features/Kobal/Shutterstock Directed by Alejandro Gonzalez Inarritu. Screenplay by Guillermo Arriaga, story by Arriaga and Alejandro Gonzalez Inarritu. Starring Sean Penn, Naomi Watts, Benicio del Toro, Charlotte Rampling, Danny Huston, John Rubinstein, Clea Duvall, Eddie Marsan, Melissa Leo.
Penn’s performance in “21 Grams” got largely overlooked when the movie opened in 2003, having the misfortune of coming out the same year as his Oscar-winning turn in “Mystic River” (the BAFTAs gave him Best Actor nominations for both films). It’s a shame, because he’s truly mesmerizing in Alejandro Gonzalez Inarritu’s ensemble drama about the effects of a car crash on a wide variety of people. He plays Paul Rivers, a critically ill mathematics professor in desperate need of a heart transplant. Told in Inarritu’s signature jagged, nonlinear storytelling style, this is a powerful look at the ways our lives intersect, for better or for worse.
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7. THE THIN RED LINE (1998)
Image Credit: 20th Century Fox/Kobal/Shutterstock Written and directed by Terrence Malick, based on the novel by James Jones. Starring Sean Penn, Adrien Brody, Jim Caviezel, Ben Chaplin, George Clooney, John Cusack, Woody Harrelson, Elias Koteas, Nick Nolte, John C. Reilly, John Travolta.
It’s hard to pick a standout actor from Terrence Malick’s World War II epic — the first film the notoriously reclusive director made since 1978’s “Days of Heaven” 20 years prior — considering how dense and rich the ensemble is. But Penn certainly holds his own as 1st Sgt. Welsh, a cynical soldier bucking up against the spiritually optimistic Pvt. Bell (Jim Caviezel). It’s one of many metaphorical battles taking place while the greater conflict ensues. Though it’s filled with stunning battle sequences, this is a more philosophical take on warfare, a contemplation of man’s inclination towards conflict and our place in the universe overall.
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6. AT CLOSE RANGE (1986)
Image Credit: Orion/Kobal/REX/Shutterstock Directed by James Foley. Screenplay by Nicholas Kazan, story by Elliott Lewitt and Kazan. Starring Sean Penn, Christopher Walken, Mary Stuart Masterson, Crispin Glover, Tracey Walter, Chris Penn.
James Foley’s “At Close Range” is a gritty, nasty little thriller that’s also a surprisingly powerful examination of the frayed bond between negligent fathers and needy sons. Based on a true story, it provides Penn with one of his best early roles as Brad Whitewood, Jr., a teenager living in poverty with his mother, grandmother and younger brother (played by Sean’s late sibling Chris Penn). His father, Brad, Sr. (Christopher Walken), is a career criminal leading a life his impressionable kid hopes to one day emulate. Sensing this, the elder Whitewood enlists the boy to help with his misdeeds, which quickly escalate from theft and burglary to murder.
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5. FAST TIMES AT RIDGEMONT HIGH (1982)
Image Credit: Moviestore/Shutterstock Directed by Amy Heckerling. Screenplay by Cameron Crowe, based on his book. Starring Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Phoebe Cates, Brian Backer, Robert Romanus, Ray Walston, Forest Whitaker, Vincent Schiavelli, Eric Stoltz, Nicolas Cage, Anthony Edwards.
Penn shot to stardom with this raunchy high school comedy, which served as a launching pad for several soon-to-be A-listers. He plays Jeff Spicoli, a stoner who spends his days surfing and trying to get laid, leaving no time for studies. “Fast Times at Ridgemont High” got its start as an undercover expose about the lives of Southern California teenagers written by Cameron Crowe, who later turned it into a script. Directed by Amy Heckerling, it features some of the frankest discussions of sex ever heard in a high school comedy, setting it apart from the likes of “Porky’s” and other films from the era that featured lecherous boys giggling over naked girls.
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4. SWEET AND LOWDOWN (1999)
Image Credit: Magnolia/Sweetland/Doumanian Prods/Kobal/REX/Shutterstock Written and directed by Woody Allen. Starring Anthony LaPaglia, Brian Markinson, Gretchen Mol, Samantha Morton, Sean Penn, Uma Thurman, James Urbaniak, John Waters.
Jazz has functioned almost like an off-screen character in Woody Allen’s oeuvre, so it’s not surprising he would eventually make a movie about a musician. Penn plays Emmet Ray, an immensely confident 1930s guitarist who lives forever in the shadows of Django Reinhardt. The heart of the story lies in his romance with a cheerful deaf girl (Samantha Morton), who sticks by his side despite his run-ins with the mob and an affair with a floozy (Uma Thurman). Both Penn — who flawlessly plays the guitar in the film— and Morton were nominated at the Oscars in Best Actor and Best Supporting Actress, respectively.
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3. MYSTIC RIVER (2003)
Image Credit: Warner Bros/Kobal/Shutterstock Directed by Clint Eastwood. Written by Brian Helgeland, based on the novel by Dennis Lehane. Starring Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, Laura Linney.
Penn won his first Oscar as Best Actor for Clint Eastwood’s haunting examination of how childhood wounds give way to adult pain. Based on a novel by Dennis Lehane, the film centers on three friends: Jimmy Marcus (Penn) an ex-con; Dave Boyle (Tim Robbins), a blue collar workerl and Sean Devine (Kevin Bacon), a police detective. As young boys, their innocence was shattered when Dave was abducted by two men posing as police officers. Years later, their bond is further tested when Jimmy’s daughter (Emmy Rossum) is murdered, and Dave is a suspect in the investigation being lead by Sean and his partner (Laurence Fishburne).
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2. DEAD MAN WALKING (1995)
Image Credit: Demmie Todd/Working Title/Havoc/Kobal/REX/Shutterstock Written and directed by Tim Robbins, based on the book by Sister Helen Prejean C.S.J. Starring Susan Sarandon, Sean Penn, Robert Prosky, Raymond J. Barry, R. Lee Ermey, Scott Wilson.
A stunningly powerful work of cinematic activism, Tim Robbins’s “Dead Man Walking” makes as compelling a case against capital punishment as any film ever made. Based on a true story, it features Susan Sarandon as Sister Helen Prejean, a nun who establishes a special bond with death row inmate Matthew Poncelet (Penn), who was locked up for a violent murder that wasn’t as clear cut as it first appeared. Robbins and company never take sides, instead presenting the story fairly and objectively, all the way up to its devastating conclusion. Sarandon won the Oscar as Best Actress, while Penn earned his first nomination as Best Actor.
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1. MILK (2008)
Image Credit: Focus/Kobal/REX/Shutterstock Directed by Gus Van Sant. Written by Dustin Lance Black. Starring Sean Penn, Emile Hirsch, Josh Brolin, Diego Luna, James Franco, Alison Pill, Victor Garber, Denis O’Hare, Joseph Cross.
Penn completely embodies Harvey Milk, which is no small feat considering we have the Oscar-winning documentary “The Times of Harvey Milk” to compare it to. The pioneering LGBTQ rights activist made history as California’s first openly gay elected official before his life was cut tragically short by fellow politician Dan Brown (Josh Brolin). It’s a stunningly empathetic performance that helps make Gus Van Sant’s biographical drama an emotional powerhouse. The film brought Penn his second Oscar in Best Actor, winning an additional prize for Dustin Lance Black’s screenplay and earning six more nominations, including Best Picture.
