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Sean Penn Is a Hollywood Heavyweight: Your Guide to the Films That Made Him a Star

Take a look back at the actor's best films!

Gifted actor, writer and director, Sean Penn has taken home two Academy Awards among other accolades for the best Sean Penn movies. But the 64-year-old multi-talent has also become one of today’s leading political and social activists, having recently made a documentary, Superpower, which chronicles his seven trips to Ukraine before and after Russian forces invaded.

Born Sean Justin Penn in Santa Monica, California on August 17, 1960, Sean had Hollywood blood in his DNA from the get-go. Dad was actor and director Leo Penn and his mother was actress Eileen Ryan. Penn was raised in a well-to-do environment, living in Malibu, attending Malibu Park Junior High and Santa Monica High School alongside fellow childhood pals Emilio Estevez and Charlie Sheen.

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sean penn holding award
Sean Penn (2004)Michael Caulfield Archive / Contributor / Getty

His dad directed many Little House on the Prairie episodes, and cast his son as an extra in 1974, launching Penn’s career. Penn explained in an interview with Esquire, “In my teens, I fell in love with the movies…” From the prairie, the powerhouse performer was on his way to feature films, showcasing his intensely moving work while drawing media attention for his stormy private life and political viewpoints. In his first few films, Penn was a strong-headed, unruly youth, but as his career progressed, he was noticed by critics as a mature, versatile and talented actor with many dynamic performances.

Here is a look at the best Sean Penn movies.

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Taps (1981): Sean Penn movies

Penn made his film debut in this action drama where he played Alex Dwyer, a military high school cadet. The cadets (among them Tom Cruise) seize the campus and refuse entry of the construction crew wanting to demolish their school to put up condos. 

Fast Times at Ridgemont High (1982)

Switching gears, Penn played the role of surfer-stoner Jeff Spicoli who popularized the word “dude,” which has become part of the English lexicon. His performance as Spicoli is ranked #9 on Premiere Magazine’s 100 Greatest Movie Character of all time. 

Bad Boys (1983): Sean Penn movies

As Mick O’Brien, a troubled youth in this drama, the role earned Penn favorable reviews and put him into serious actor category. A Chicago crime kid, O’Brien is sent to reform school after accidentally killing a rival’s kid brother. To add authenticity to the thug, Penn wanted to have his perfect teeth filed down and add a few cracked ones to boot. But Penn’s mom, a dentist’s daughter, intervened and said her son was going too far and Penn’s perfect teeth remained. 

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The Falcon and the Snowman (1985)

Penn played Andrew Daulton Lee in the film which closely followed an actual criminal case. Lee was a former drug dealer, convicted of spying for the Soviet Union and originally sentenced to life in prison, but paroled in 1988. Being a firm believer in rehabilitation, Penn hired Lee to be his personal assistant. 

At Close Range (1986): Sean Penn movies

Penn starred in this crime drama and received high critical praise for his role of Brad Jr. to Christopher Walken’s Brad, Sr., a notorious professional criminal. At his sons’ urging, Senior agrees to plan petty theft heists, but his true evil nature is revealed when he sacrifices his sons for his own life.

Shanghai Surprise (1986)

It was no surprise that this film flopped at the box office. First conceived as star billing of husband and wife, Madonna and Penn, the adventure and romance did not capture audiences.

Colors (1988): Sean Penn movies

Penn bounced back from his Shanghai Surprise debacle with his role as a hot-headed young cop who is shown the ropes by a veteran partner (Robert Duvall) in the dangerous gang-controlled neighborhoods of Los Angeles. A look at the real gang culture, enforced by the colors members wear, gave authenticity to the violence that exploded

Causalities of War (1989)

Good soldier, bad soldier…. Michael J. Fox is the former while Penn plays one of the soliders who rapes and kills a young Vietnamese girl during the Vietnam War. The depiction of this crime serves as a microcosm of the realities of war.

We’re No Angels (1989): Sean Penn movies

Robert DeNiro and Penn are escaped convicts who find refuge with the Church when they are mistaken for two priests. The pair is keen to flee into Canada, but are unable to do so without the help of Molly (Demi Moore). Penn has credited working with Robert DeNiro as the catalyst for him becoming a serious actor. 

State of Grace (1990)

Penn plays Terry Noonan, who returns home to Hell’s Kitchen after being gone for a decade. He soon hooks up with childhood pals involved in the Irish mob while also rekindling things with Kathleen, an old flame played by Penn’s future wife, Robin Wright. Several incidents in the film are based on actual testimony given by various New York mobsters. 

Carlito’s Way (1993): Sean Penn movies

If you were wondering where Penn was in this film, he was almost unrecognizable with frizzy hair and thin rimmed glasses as corrupt lawyer David Kleinfeld in this gangster movie. Critics said his performance was brilliant.

Dead Man Walking (1995)

Penn received an Oscar nomination for his role playing a racist murderer on death row who pleaded with a caring nun (Susan Sarandon) to save his life. 

The Game (1997): Sean Penn movies

He plays the brother of wealthy Nicki Van Orton (Michael Douglas), who involves him in a mind snapping scheme. 

The Thin Red Line (1998)

Penn landed the lead role of Sgt. Eddie Walsh in this anti-war film based on James Jones’ autobiographic novel that focuses on the conflict at Guadalcanal during WW II. In a very minor role, you can spy George Clooney

Sweet and Lowdown (1999): Sean Penn movies

In this Woody Allen comedy biopic, Penn scored another Oscar nomination as egotistical jazz guitarist Emmett Ray, an arrogant, obnoxious, irresponsible man who was also one of the best guitarists in the world. Penn was touted for his comedic timing in this role. 

I Am Sam (2001)

His third Oscar nomination came after portraying Sam Dawson, a mentally handicapped father fighting for custody of his seven-year-old daughter after the homeless mother abandons them both. His daughter is taken away from him, so he finds a lawyer who handles pro bono cases. Is it true that all you need is love? 

Mystic River (2003): Sean Penn movies

This Boston crime drama set in 1975 brought Penn his first Academy Award win and deservedly so. He plays an anguished father seeking revenge for his daughter’s murder in this gut-wrenching movie directed by Clint Eastwood. Authenticity in the Boston environs, dialect and anguish.

21 Grams (2003)

Penn plays Paul Rivers, a mortally ill mathematician college professor who endures a loveless marriage.  A terrible accident brings together his wife, Rivers and an ex-convict who has found Jesus.

The Assassination OF Richard Nixon (2004): Sean Penn movies

This time out, Penn is Samuel Bicke, a character based on the real Samuel Byck, who attempts and fails to assassinate President Richard Nixon in 1974. “It was the hardest thing I’ve ever done,” Penn shared with Oprah Winfrey. “I think I did this one well. [But] I’d go back and fix some things in everything I’ve done.”

All the King’s Men (2006)

While you might think that all of Penn’s films were critical hit, this movie, where he portrays governor Willie Stark, a character based on Huey Long, was a critical and commercial flop. In fact, Forbes said it was the biggest flop of the last five years preceding it.

Milk (2008): Sean Penn movies

Undeterred, Penn earned positive reviews for his portrayal of real-life politician and gay rights icon Harvey Milk in this biopic. For his strong performance, Penn received his second Oscar for Best Actor.

Fair Game (2010)

Penn stars as real life Joseph C. Wilson, whose wife, Valerie Plame, was outed as a CIA agent by Bush adviser Scooter Libby. This was done in retaliation for an article Wilson wrote exposing the claim that Iraq was building a nuclear bomb as a rationale for invading the country. The film was based upon Plame’s memoir, Fair Game.

The Tree of Life (2011): Sean Penn movies

Focusing on a Texas family in the 1950s, the film follows the life journey of Jack, from his innocent childhood to his adult years. Penn plays the adult Jack, a lost soul in the modern world. Brad Pitt plays a young Jack’s dad. 

The Gunman (2015)

In this French American action thriller based on the novel The Prone Gunman, Penn plays Jim Terrier, a sniper on a mercenary assassination team who kills the minister of mines of the Congo

Licorice Pizza (2021): Sean Penn movies

In this comedy/drama, Penn portrays Jack Holden, as actor based on the real-life Hollywood icon William Holden. It was a brief appearance.

Fast Facts:

  • Penn served 32 days in jail in 1987 for hitting an extra.
  • He quit smoking for a while on his 40th birthday for health reasons. Before that, he was known as one of Hollywood’s heaviest smokers, smoking at least four packs of cigarettes a day. 
  • Flew to Haiti in January 2010 to help the relief effort after the earthquake.
  • His father Leo Penn had been blacklisted in the 1950s for his political beliefs
  • Penn’s At Close Range director, James Foley, served as best man at Penn and Madonna’s 1985 wedding. 
  • He made his feature film directorial debut with The Indian Runner in 1991. The film is based on Bruce Springsteen’s song “Highway Patrolman.”
  • Penn directed several music videos, including Shania Twain’s “Dance With the One That Brought You” and Lyle Lovett’s “North Dakota.”

Penn has shared that he carries around in his wallet a long quote by writer William Saroyan that he says serves as a guide for living his best life.

“Be the inferior of no man, or of any men be superior. Remember that every man is a variation of yourself. In the time of your life, live — so that in that wondrous time you shall not add to the misery and sorrow of the world, but shall smile to the infinite delight and mystery of it.” 

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