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Sean Penn presents the Oscar® for Best Picture during the live ABC Telecast of The 87th Oscars® at the Dolby® Theatre in Hollywood, CA on Sunday, February 22, 2015. Credit/Provider: Michael Yada / ©A.M.P.A.S. Copyright: ©A.M.P.A.S.
Sean Penn is one of the greatest actors of his generation and has now joined the Academy Awards three-timers club!
Beginning his acting career in the early ’80s with groundbreaking films like ‘Taps’, ‘Fast Times at Ridgemont High’, and ‘Casualties of War’, he would continue giving unforgettable performances in the ’90s with films like ‘State of Grace’, ‘Carlito’s Way’, ‘The Game’, and ‘Dead Man Walking’, which earned him his first Oscar nomination for Best Actor.
But it was 2003 before he received his first Best Actor Oscar for his work in director Clint Eastwood’s ‘Mystic River’. Penn would be rewarded with another Best Actor Oscar for his portrayal of Harvey Milk in 2008’s ‘Milk’, directed by Gus Van Sant.
“Some search for battle, others are born into it…”
Release Date: Sep 26, 2025
Run Time: 2 hr 42 min
Budget: $175,000,000
Now, with his recent Best Supporting Actor win at the 98th Academy Awards for his work in Paul Thomas Anderson’s ‘One Battle After Another’, Penn joins the likes of Daniel Day-Lewis, Frances McDormand, Jack Nicholson, Meryl Streep, Ingrid Bergman, Walter Brennan, and Katharine Hepburn, who all have received three or more competitive acting Oscars (Hepburn has four).
In honor of his recent Oscar win, Moviefone is counting down the 20 best films of Sean Penn’s long and impressive career.
Let’s begin!
Related Article: Executive Producer Sean Penn Talks ‘Words of War’ and Freedom of Speech
Sean Penn in ‘The Gunman’. Photo: Open Road Films.
Eight years after fleeing the Congo following his assassination of that country’s minister of mining, former assassin Jim Terrier (Penn) is back, suffering from PTSD and digging wells to atone for his violent past. After an attempt is made on his life, Terrier flies to London to find out who wants him dead — and why. Terrier’s search leads him to a reunion with Annie (Jasmine Trinca), a woman he once loved, who is now married to an oily businessman with dealings in Africa.
Release Date: Mar 20, 2015
Run Time: 1 hr 55 min
Budget: $40,000,000
Paul Rivers (Penn), an ailing mathematician lovelessly married to an English émigré; Christina Peck (Naomi Watts), an upper-middle-class suburban housewife and mother of two girls; and Jack Jordan (Benicio del Toro), a born-again ex-con, are brought together by a terrible accident that changes their lives.
“How much does life weigh?”
Release Date: Jan 16, 2004
Run Time: 2 hr 4 min
Budget: $20,000,000
The story of Gary Valentine (Cooper Hoffman) and Alana Kane (Alana Haim) growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.
“You’ve come a long way, baby.”
Release Date: Dec 25, 2021
Run Time: 2 hr 13 min
Budget: $40,000,000
The true story of a disillusioned military contractor employee (Timothy Hutton) and his drug pusher childhood friend (Penn) who became walk-in spies for the Soviet Union.
“They came from the best of families. And they committed the worst of crimes.”
Release Date: Jan 25, 1985
Run Time: 2 hr 12 min
Budget: $12,000,000
The impressionistic story of a Texas family in the 1950s. The film follows the life journey of the eldest son, Jack (Penn), through the innocence of childhood to his disillusioned adult years as he tries to reconcile a complicated relationship with his father (Brad Pitt). Jack finds himself a lost soul in the modern world, seeking answers to the origins and meaning of life while questioning the existence of faith.
Release Date: May 27, 2011
Run Time: 2 hr 19 min
Budget: $32,000,000
Sean Penn in ‘The Thin Red Line’. Photo: 20th Century Fox.
The story of a group of men, an Army Rifle company called C-for-Charlie, who change, suffer, and ultimately make essential discoveries about themselves during the fierce World War II battle of Guadalcanal. It follows their journey, from the surprise of an unopposed landing, through the bloody and exhausting battles that follow, to the ultimate departure of those who survived.
“Every man fights his own war.”
Release Date: Jan 15, 1999
Run Time: 2 hr 51 min
Budget: $52,000,000
14. ‘Taps’ (1981)
Military cadets take extreme measures to ensure the future of their academy when its existence is threatened by local condo developers.
““This school is our home, we think it’s worth defending.””
Release Date: Dec 20, 1981
Run Time: 2 hr 6 min
Budget: $14,000,000
Brad Whitewood Jr. (Penn) lives in rural Pennsylvania and has few prospects. Against his mother’s wishes, he seeks out his estranged father (Christopher Walken), the head of a gang of thieves in a nearby town. Though his new girlfriend (Mary Stuart Masterson) supports his criminal ambitions, Brad Jr. soon learns that his father is a dangerous man. Inspired by the real events that led to the end of the Johnston Gang, who operated in the northeastern United States in the 1970s.
“Like father. Like son. Like hell.”
Release Date: Apr 18, 1986
Run Time: 1 hr 51 min
Budget: $6,500,000
During the Vietnam War, a soldier (Michael J. Fox) finds himself the outsider of his own squad when they unnecessarily kidnap a female villager.
“Even in war… murder is murder.”
Release Date: Aug 18, 1989
Run Time: 1 hr 53 min
Budget: $22,500,000
In honor of his birthday, San Francisco banker Nicholas Van Orton (Michael Douglas), a financial genius and a cold-hearted loner, receives an unusual present from his younger brother, Conrad (Penn): a gift certificate to play a unique kind of game. In nary a nanosecond, Nicholas finds himself consumed by a dangerous set of ever-changing rules, unable to distinguish where the charade ends and reality begins.
“What do you get for the man who has everything…?”
Release Date: Sep 12, 1997
Run Time: 2 hr 9 min
Budget: $50,000,000
(L to R) Ben Stiller and Sean Penn in ‘The Secret Life of Walter Mitty’. Photo: 20th Century Fox.
A timid magazine photo manager (Ben Stiller), who lives life vicariously through daydreams embarks on a true-life adventure when a negative goes missing.
“Stop dreaming. Start living.”
Release Date: Dec 25, 2013
Run Time: 1 hr 54 min
Budget: $90,000,000
A death row inmate (Penn) turns for spiritual guidance to a local nun (Susan Sarandon) in the days leading up to his scheduled execution for the murders of a young couple.
Release Date: Jan 2, 1996
Run Time: 2 hr 2 min
Budget: $11,000,000
The lives of three men (Penn, Tim Robbins and Kevin Bacon) who were childhood friends are shattered when one of them suffers a family tragedy.
“We bury our sins, we wash them clean.”
Release Date: Oct 15, 2003
Run Time: 2 hr 18 min
Budget: $25,000,000
In the 1930s, jazz guitarist Emmet Ray (Penn) idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman (Samantha Morton).
Release Date: Dec 3, 1999
Run Time: 1 hr 35 min
Budget: $29,750,000
A confident young cop (Penn) is shown the ropes by a veteran partner (Robert Duvall) in the dangerous gang-controlled barrios of Los Angeles, where the gang culture is enforced by the colors the members wear.
“70,000 gang members. One million guns. Two cops.”
Release Date: Apr 29, 1988
Run Time: 2 hr
Budget: $6,000,000
Sean Penn in ‘Carlito’s Way’. Photo: Universal Pictures.
Free after years in prison, Carlito Brigante (Al Pacino) intends to give up his criminal ways, but it’s not long before the ex-con is sucked back into the New York City underworld.
“He’s got a good future if he can live past next week.”
Release Date: Nov 10, 1993
Run Time: 2 hr 24 min
Budget: $30,000,000
4. ‘Milk’ (2009)
The true story of Harvey Milk (Penn), the first openly gay man ever elected to public office. In San Francisco in the late 1970s, Harvey Milk becomes an activist for gay rights and inspires others to join him in his fight for equal rights that should be available to all Americans.
Release Date: Jan 30, 2009
Run Time: 2 hr 8 min
Budget: $20,000,000
The movie follows a group of high school students growing up in Southern California. Stacy Hamilton (Jennifer Jason Leigh) and Mark Ratner (Brian Backer) are looking for love, and are helped along by their older classmates, Linda Barrett (Phoebe Cates) and Mike Damone (Robert Romanus). Jeff Spicoli (Penn), a perpetually stoned surfer faces-off with the resolute teacher, Mr. Hand (Ray Walston). Hilarity and heartbreak ensue.
“At Ridgemont High, only the rules get busted!”
Release Date: Aug 13, 1982
Run Time: 1 hr 30 min
Budget: $4,500,000
Hell’s Kitchen, New York. Terry Noonan (Penn) returns home after a ten-year absence. He soon reconnects with Jackie (Gary Oldman), a childhood friend and member of the Irish mob, and rekindles his love affair with Jackie’s sister Kathleen (Robin Wright).
“… where crime is a family affair.”
Release Date: Sep 14, 1990
Run Time: 2 hr 15 min
Budget: $7,000,000
Sean Penn as Col. Steven J. Lockjaw in ‘One Battle After Another.’ A Warner Bros. Pictures Release. Photo Credit: Photo Courtesy Warner Bros. Pictures
Washed-up revolutionary Bob (Leonardo DiCaprio) exists in a state of stoned paranoia, surviving off-grid with his spirited, self-reliant daughter, Willa (Chase Infiniti). When his evil nemesis (Penn) resurfaces after 16 years and she goes missing, the former radical scrambles to find her, father and daughter both battling the consequences of his past.
“Some search for battle, others are born into it…”
Release Date: Sep 26, 2025
Run Time: 2 hr 42 min
Budget: $175,000,000
