Sean Penn: His 15 Best Films

In almost 35 years on screen, Sean Penn has acted in more than 50 films and counting, and directed a further four, with another on the way. What follows is Esquire’s entirely subjective selection of 15 worth watching again, in release order

1 | Fast Times At Ridgemont High (Amy Heckerling, 1982)

At least in America, where thanks to Penn (and Phoebe Cates’ breasts) this high-school movie remains a cherished cult, his breakthrough stands as arguably his most iconic performance.

He plays Jeff Spicoli, the California stoner-surfer dude with the heart of gold, the bagel tucked into his pants and the admirable philosophy: “All I need are some tasty waves, cool buzz and I’m fine.” For a clever man, Penn does a very convincing stupid. It made him a star at 21.

2 | The Falcon and the Snowman (John Schlesinger, 1985)

Again employing the shot-away quality familiar from Fast Times…, as if a firework just exploded in his face, Penn plays an in-over-his-head, rich kid drug dealer in this Seventies-set spy drama, from the director of Midnight Cowboy and Marathon Man – with whom Penn predictably fell out. With his oversized aviators and flared suit, initially he’s twitchy, nervy and funny. Later, as his character succumbs to addiction, he’s almost painfully intense. Debut appearance for the pencil moustache.

Blond and bulked up, Penn is the archetypal all-American bad boy in this grimy rural crime drama. His scenes with Christopher Walken as his sociopath father achieve a combustible mixture of savagery and sensitivity. It was at this point that, for all the attention swirling around his marriage to Madonna, his reputation as the most gifted actor of his generation of US film actors began to be taken as read. While Tom Cruise dominated the box office with Top Gun, Penn was the critics’ choice.

Penn is the cocksure junior partner to Robert Duvall’s hard-arse veteran cop in Hopper’s tough portrait of the South Central and East LA gang wars. Penn’s character seems an arrogant prick at first, more concerned with his hair than fighting crime, but he slowly emerges as brave and even endearing. Penn is plausibly tough in the action sequences (he has the pumped-up body of an Eighties action star) but he does wounded masculinity as delicately as any Seventies method man. Plus, none of them had Ice-T rapping on the soundtrack. “What up, homes?” etc.

Nobody hoping for a career as a popular box office star would have taken Penn’s part in the inconsistent De Palma’s grim Vietnam parable. So while his contemporaries were eyeing action franchises, Penn was starring opposite straight-arrow Michael J. Fox as Sergeant Meserve, a soldier brutalised by combat into a hateful, vicious rapist and killer, a bully whose face contorts with fear and hate – and to accommodate the tobacco he chews throughout.

Penn struggled with the psychological impact of walking in his slimeball character’s slip-ons, but from the audience’s point of view, this is one of his most enjoyable performances, a scene-stealing supporting turn as Kleinfeld, the paranoiac, bubble-permed, cigarillo-smoking, coke-snorting criminal lawyer to Al Pacino’s Puerto Rican drug dealer in De Palma’s disco-era mob romp.

With his lazy Louisiana drawl, his well kempt bouffant, his wispy moustache and his folky chin beard, plus his ability to smoke cigarettes with cruel intent even while cuffed at the waist, Penn’s Matthew Poncelet, the murderer at the centre of Robbins’ impassioned death row melodrama, is one of his most memorable performances, a study in rage, fear, defiance, resignation, guilt and sadness, as tight and controlled – no histrionics here – as the restraints that tie him to the gurney. The New Yorker’s John Lahr described Poncelet’s final breakdown as “among the high water marks of contemporary acting”. Penn received his first Best Actor Oscar nomination.

Years later, on the release of the weird and wonderful Tree of Life (2011), star and director would fail to see eye to eye but this was a happier collaboration, with Penn one of the few of the A-list actors assembled for Malick’s WWII epic to enjoy more than a small fraction of screen time. (George Clooney, John Travolta, John Cusack, Woody Harrelson and others were not quite so lucky.) Still, the play’s the thing, as Penn often says, and this sublime, metaphysical war movie is one of the best films he has been associated with.

Forget Shanghai Surprise (1986): Penn can do comedy. A lovely performance as the dapper, degenerate guitar prodigy, Emmett Ray – a Django Reinhardt manqué – in Allen’s stylish jazz age tribute. Despite his character being ignorant, obnoxious, solipsistic, drunk, dishonest, unfeeling, profligate, and ultimately, tragic, Penn – who learned to play guitar for the role – makes Ray funny and even sympathetic, and received another Best Actor Oscar nomination for his efforts.

Penn’s third film as director – following The Indian Runner (1991) and The Crossing Guard (1995) – with Jack Nicholson quietly magnificent as a retired cop destroyed by his search for a child-killer. Worth seeing for one scene alone: when Nicholson’s character breaks the news of the girl’s murder to her parents. “There are such devils,” he says, giving name to the horror that lurks in the shadows of Penn’s doleful early films as a director.

The New York Times critic AO Scott called Penn’s performance in this film “one of the definitive pieces of screen acting in the last half century, the culmination of a realist tradition that began in the old Actors Studio and begat Brando, Dean, Pacino and De Niro…” Which would make it close to the greatest piece of screen acting ever. Eastwood’s chilling Boston crime drama, based on a Dennis Lehane novel, is about the explosive effects on a tight-knit Irish-Catholic community of the killing of a 19-year-old girl, as well as the awful secrets buried in the pasts of its middle-aged protagonists. Penn plays the dead girl’s father, Jimmy, the snarling, tough guy owner of the local corner store. He projects immense power and danger, plus animalistic rage. It’s said it took eight men to restrain him during the scene where he learns of his daughter’s death, and he had to be fed oxygen between takes. The Best Actor Oscar duly followed.

Based on John Krakauer’s book about Chris McCandless, who turned his back on conventional society and reinvented himself, in the tradition of Emerson and Thoreau, as Alexander Supertramp before, ultimately, dying in an abandoned bus in Alaska. A sad story, then, but Penn’s film is more epic romance than nihilistic wallow. A tribute to the big skies of the American West and the free spirit of the counterculture, it’s gorgeous to look at and moving in its belief that human relationships are what matters: we are our family, our friends, our lovers.

Another gigantic performance – warm, witty and wise – and another Oscar for Best Actor for this turn as the real-life, rabble-rousing activist and politician Harvey Milk in Gus Van Sant’s highly affecting film about the gay rights movement in Seventies San Francisco. Penn’s Milk is vulnerable, funny, seductive, charismatic, boyish, a loveable square with a big, wide, open smile that creases up his face. The physical transformation is subtle in its specifics – Penn flattens his hair, adjusts his posture, flutters his hands – but phenomenal in its effect, as if Penn really is possessed by the spirit of Harvey. His Oscar acceptance speech was warm but pointed: “Thank you, you commie, homo-loving sons of guns.” Liberal Hollywood at its best.

14 | This Must Be The Place (Paolo Sorrentino, 2011)

A strange and remarkable road movie from the Italian maestro, in which a zonked-out former pop star traces the Nazi who brutalised his estranged Holocaust-survivor father. Penn’s Cheyenne looks as sad as The Cure’s Robert Smith, seems as frail as Ozzy Osbourne, lives in the kind of Dublin mansion you can imagine Bono inhabiting and seems to have borrowed his spectacles from Woman’s Hour’s Jenni Murray. He talks in a soft, Emo Philips voice and walks like a sultry teenager. Weirder still, Penn fully inhabits the role and, in the process, somehow carries this most implausible of films. Impossible to imagine any of his A-list peers taking this role. Even harder to imagine any of them pulling it off…

Not Penn’s most cerebral film, but a superior thriller. He plays a US marine-turned-mercenary-assassin-turned-aid-worker who must battle not only his conscience but also “post-concussion syndrome” and a classy cast of rogues led by Mark Rylance and Javier Bardem. Ray Winstone is his grizzled sidekick; Idris Elba a sharp-suited smoothie. The action pinballs from war-torn Kinshasa to the City of London, to rural Spain. There’s a terrific punch-up in a London boozer, and a gory showdown in a bullring. Fans of Morel’s Taken (2008) will be impressed.

*** MORE COVER STARS:Sean Penn Is Esquire’s March Cover StarRobert Downey Jr: To The Edge And BackGeorge Clooney: The Full Interview***


Through flashbacks, this biographical film records the career of Harvey Milk who became America’s first openly gay person to be elected to public office on the San Francisco Board of Supervisors following a successful campaign led by his young partner and campaign manager Scott Smith. A year later, he is assassinated by his former conservative colleague Dan White.



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Second Oscar for ‚Milk‘

Stepping back in front of the cameras, Penn won his second Academy Award for best actor for his portrayal of the first openly gay politician, Harvey Milk, in the film Milk (2008). The film, directed by Gus Van Sant, received more than 40 award nominations and performed well at the box office. Penn later had a supporting role in the Malick film Tree of Life (2011). That same year, he starred in the independent drama This Must Be the Place, in which Penn played a former rock star who searched for a Nazi war criminal to avenge his father.

Penn tackled an infamous role in Gangster Squad (2013), a movie about the clash between law enforcement and organized crime in Los Angeles in the 1940s and 1950s. He portrayed the notorious crime boss Ryan Gosling played a member of the police force who opposes him. The project had been scheduled for a fall 2012 release but was delayed because of the film’s shootout scene in a movie theater, which evoked memories of the July 2012 shootings inside a Colorado movie theater. Warner Brothers, the studio behind Squad, subsequently made edits to the film.

Penn had a small supporting role in 2014’s The Secret Life of Walter Mitty, starring Ben Stiller, and is featured in the 2015 action drama The Gunman. He also made headlines after the February 2015 Academy Awards telecast: Penn uttered an off-color joke about friend Alejandro Gonzales Iñárritu while announcing the director’s Birdman win for best picture.

Second Oscar for 'Milk'

Personal Life

Seven years after his divorce from Madonna, Penn and House of Cards star Robin Wright wed in 1996. The couple has two children. The couple divorced in 2010 in a non-amicable split. In early 2014, reports surfaced that Penn was dating a fellow Oscar winner, actress Charlize Theron. They quietly got engaged that December, but by the following June, it was revealed that the couple had ended their relationship.

In August 2020, Penn tied the knot with Leila George, his girlfriend of four years.

Personal Life

21. (I) (2008)

The story of Harvey Milk and his struggles as an American gay activist who fought for gay rights and became California’s first openly gay elected official.

Director:Gus Van Sant | Stars:Sean Penn, Josh Brolin, Emile Hirsch, Diego Luna