Every Sean Penn Movie Ranked Worst To Best

In 1986 Sean Penn starred as Glendon Wasey, a fortune-hunter looking for a quick exit out of China, alongside his then-wife, Madonna, playing Gloria Tatlock, a nurse/missionary, in the notoriously terrible, "Shanghai Surprise." This film goes in the category of real-life lovers playing lovers so terribly on film, it makes everyone wonder how long the relationship will last. Think of it as a "Gilli" of the '80s. The story is a predictable rom-com about two Americans living in China in the late '30s. They are brought together while searching for a large quantity of opium that has vanished. Gloria needs the opium as pain medication for her patients, and Glendon thinks it could be his ticket out of China.

The AV Club said the film was "Limply, tardily trying to cash in on the success of the Indiana Jones movies." And Empire said the film was "Really, really bad. Production company-destroyingly bad," explaining that "Shanghai Surprise" was the "beginning of the end" for the production company backing this film. Of course, there were those who simply watched the film because they were Madonna fans, and they probably liked it better than the rest of us, accounting for the slightly higher ratings with audiences than critics on Rotten Tomatoes.

In "The Gunman" Sean Penn plays Jim Terrier, an ex-special forces soldier and former assassin, who now works drilling wells after an assassination in the Congo forced him into hiding. When someone makes an attempt on his life, Terrier must venture back into the world of mercenaries, despotic warlords, and corporate greed in Africa if he wants to discover who wants him dead. Co-starring Javier Bardem and Idris Elba, one might expect this film to be excellent, but it doesn't play out that way. We have to agree with Richard Roeper of the Chicago Sun Times, when he said "Rarely, though, have two Academy Award-winning actors been so stunningly off the mark in the same movie." Considering the director of the film was none other than Pierre Morel, the man behind "Taken" and "District B13" the film seemed to have so much promise — but it undoubtedly fell short. We aren't the only ones who think this film is a pass, with a 16% critic rating and 31% with audiences on Rotten Tomatoes.

"The Weight of Water" is about a photojournalist, Jean Janes, traveling in a yacht off the coast of New England with her husband Thomas (Sean Penn), his brother Rich (Josh Lucas), and Rich's beautiful girlfriend Adaline (Elizabeth Hurley). The goal is to photograph the site of an axe murder from 1873, that Jean is investigating. The story is told through two timelines, one in the present featuring Jean's growing jealousy and suspicion of her husband and his brother's girlfriend, and another during the murder of two Norwegian immigrants, and the woman who survived the brutal murder in the 1800s. 

The film met mixed reviews from critics. Some, like Jeffrey M. Anderson, thought the film was director Kathryn Bigelow's "most emotionally and artistically ambitious" (per Combustible Celluloid). While others, like Roger Ebert, thought the duel timeline destroyed the film, saying, "While either one of the stories could make a plausible thriller, the movie's structure undercuts them both." It seems audiences felt just about the same as critics, giving it a respective 35% and 38% ratings on Rotten Tomatoes.

In "Up at the Villa" an English widow, Mary Panton (Kristin Scott Thomas) is staying with friends in a Villa outside Florence, Italy, in the last days before WWII. Her husband's death has left her penniless, but the experience of being married to an abusive alcoholic makes her reluctant to remarry. Despite a proposal from a wealthy man she knew before her marriage, Mary finds herself drawn to Rowley Flint (Sean Penn), an American with a bad reputation. The film has plenty of intrigue, ominous fascist overtones, and gorgeous Tuscan scenery, but the movie is average. "Up at the Villa was met mixed reviews, some praising it, like Derek Elley, with Variety, who said Penn, "is confident without appearing cocky, acting much older than he looks, and with impressive restraint." While TV Guide criticized the film calling it a "Bloodless and disconcertingly cool adaptation of W. Somerset Maugham's high-class soap opera about the tangled affairs of English expatriates in pre-WWII Italy." Audiences agreed, only giving it a 36% on Rotten Tomatoes.

In 2021 Sean Penn co-starred with his daughter Dylan Penn in "Flag Day," a film he also directed, based on the true story of a prodigious counterfeiter named John Vogel (Sean) and his daughter Jennifer (Dylan). The film is about a young woman trying to reconcile her memories of how magnetic and exciting her father seemed when she was a child, with the reality of who he really is. Although some of the films Sean Penn has directed are very good, he has an erratic reputation as a director, with "Flag Day" getting mixed reviews. 

Audiences liked it more than critics, getting a 53% audience rating on Rotten Tomatoes. Some critics, like Richard Roeper from the Chicago Sun Times praised the film saying, "Sean Penn directs himself for the first time and has cast Dylan Penn, his daughter with Robin Wright, as the lead — and the two are absolutely mesmerizing together." While others thought Penn's first crack at directing himself was melodramatic.

"The Professor and the Madman" tells the story of Professor James Murray (Mel Gibson), who compiled the first edition of the Oxford English Dictionary, and a schizophrenic patient, Dr. William Chester Minor (Sean Penn), who provided over 10,000 entries. The film is based on a novel, and many critics think it should have stayed on the page, rather than disgracing the screen. Unless you studied literature or linguistics in college, you probably haven't even heard of the OED. Elizabeth Kerr of The Hollywood Reporter said, "Ironically, for a movie about words, the dialogue sparks to life only on rare occasions." 

Most critics thought the film messy, and lacking cohesion, giving it a score of 41% on Rotten Tomatoes, while audiences gave the film a mind boggling 80%. We're not exactly sure where this chasm between critics and audiences comes from. Variety said, "Gibson is fine; it's everything else that doesn't work," and "Penn's over-acting was to be expected in the role of a schizophrenic ..." We're inclined to agree with the critics on this one, but you can stream it on Netflix if you want to form your own opinion.

In "Racing with the Moon" Sean Penn plays Henry "Hopper" Nash with his co-star Nicolas Cage playing Nicky, two teenage best friends waiting to ship out with the Marines, headed for WWII. The movie is about a small town in California, Muir Point, after the U.S. has finally joined the war, with young men like Hopper and Nicky volunteering in droves after turning 18. When Hopper meets Caddie (Elizabeth McGovern), the new girl in town, at the movie theater where she works as a ticket girl, he tries to win her heart before shipping out. 

The film is a nostalgic and sweet look back at first love, and the complexities of lifelong friendships. Both Cage and Penn are excellent in their roles, with Roger Ebert giving the film 3.5 stars saying Penn, "plays the kind of kid who uses a rough exterior — smoking and shooting pool — as a kind of cover-up for the intelligence and sensitivity underneath." This film was met with mixed to favorable reviews with critics and audiences on Rotten Tomatoes.

Here we have "She's So Lovely" — when Eddie Quinn (Sean Penn) is released from a psychiatric institution after 10 years, he tries to reunite with his ex-wife Maureen (Robin Wright) who is now remarried to Joey (John Travolta) and raising three children. "She's So Lovely" explores the lives of people who struggle with substance abuse, and mental health, but as Mick LaSalle, the movie critic for the San Francisco Chronicle said, "And it features desperate, emotional characters who are presented not only without judgment, which would be miracle enough, but also with love."

This isn't a story about perfect people and perfect love, or deplorable people filled with hate, but a story about wounded hearts and broken minds, directed by Nick Cassavetes, with a screenplay by his deceased father, John Cassavetes. Others gave the film mixed reviews, like Emanuel Levy from Variety, who said, "It's hard to blame the enormously gifted Penn for his inconsistent portrayal, for the fault in his role resides in the writing." The scores on Rotten Tomatoes are consistent with a favorable, but occasionally mixed reception, with critics giving it 66%.

"Hurlyburly" is adapted from David Rabe's award-winning play about a group of Hollywood types, Eddie (Sean Penn) and Mickey (Kevin Spacey) who live together. The housemates get together with a couple friends, Phil (Chazz Palminteri) and Artie (Garry Shandling) to complain about their lives, revealing the inherent misogyny of Hollywood culture. Jonathan Lethem praised both Spacey and Penn's performances on Salon, saying, "The role of Eddie demands his deepest plunge yet into tongue-tied anguish, with triumphant results. Similarly, Spacey is invited to plumb the meaning of his remote, manipulative charm." 

The women in the film: Robin Wright, Anna Paquin, and Meg Ryan, despite being excellent actors, come across as superficial fantasies rather than real people. This may be an intentional choice of the director, Anthony Drazan, further highlighting the men's sexism. The film left some critics, like Jonathan Lethem wondering, "How many blistering insights into the precise texture of misogyny do we really need?" Maybe our criticism is colored by watching the film in a post #MeToo time-frame, rather than when it was first released in 1998. Judging by the Rotten Tomatoes scores, both critics and audiences share our mixed feelings, with audiences giving the film a 65% rating.

Although Sean Penn's role as Alex Dwyer in the 1981 film "Taps" was a supporting role in this ensemble cast, the film has been credited with launching the film careers of both Penn and Tom Cruise. Both were unknown actors when they landed their roles in this film about a group of military school cadets who carry out an armed occupation of their academy, hoping to save the site from real estate developers. The plot is far-fetched, but it is an interesting exploration of adolescence, extreme thinking, and impulse control. Roger Ebert, who gave the film three stars, compared the film to "Lord of the Flies" — we think this is an astute observation. He also said the film "works as an uncommonly engrossing story, primarily because the performances are so well done." 

The film received mostly mixed reviews from audiences and critics alike, as we see from the Rotten Tomatoes scores of 68% with critics and 67% audience ratings.

"The Assassination of Richard Nixon" is a fictionalized account of the man who plotted to kill Nixon by running a plane into the White House in 1974, but never achieved his goal to kill the president. Much like he never achieved any of his other goals in his life. Samuel J. Bicke (Sean Penn) is down on his luck. His wife Marie (Naomi Watts) has left him, and he can't hold on to a job because he is both a terrible salesman, and a self-righteous man who alienates those around him with his moralistic judgments. This is a film about a hopeless man descending into madness and finding an improbable target for his frustrations with life. 

Roger Ebert said the film, "soars on another riveting performance by Penn," giving the film 3.5 stars. The film was met with largely positive reviews, but accompanied by some mixed, with scores in the upper 60s on Rotten Tomatoes.

In 1988 Sean Penn starred as Danny McGavin, a rookie with an explosive temper partnered with Bob Hodges (Robert Duvall), a veteran, level-headed police officer, working the streets of Los Angeles on a gang task force, as tensions rise between the Crips and Bloods, and various Latino street gangs. Dennis Hopper directs Penn and Duvall in "Colors," a film about the rise of gang violence in L.A., and the tension between residents, gangs and those who police their neighborhoods. Danny must confront his own racism while falling for Louisa Gomez (Maria Conchita Alonso), a Latina woman who can't separate him from how police treat people who look like her.

The dynamic between experience and youthful exuberance in the form of two cops isn't new, but as Roger Ebert said, "Duvall and Penn are two of the best actors in America, bringing a flavor and authority to their roles that make them specific." Many have praised the non-judgmental portrayal of gang members, highlighting how the gang was the first place many of these young men found belonging and a sense of community. The New York Times said, "What 'Colors' does best is to create a sense of place and a climate of fear." Although there were some mixed reviews, "Colors" was overwhelmingly received favorably, with a 78% from critics on Rotten Tomatoes.

"Fast Times at Ridgemont High" is one of the great teen movies from the 1980s, and Sean Penn as Jeff Spicoli is one of the classic '80s characters we all associate with the genre. Although his part in the film isn't central to the main story about Stacy Hamilton (Jennifer Jason Leigh) who is in over her head in a love triangle with cool guy Mike Damone (Robert Romanus) and nice guy Mark Ratner (Brian Backer). Spicoli's epic battle of wills with Mr. Hand (Ray Walston), is hilarious and completely relatable to anyone who had a rebel streak as a teenager. As ReelViews said, "The movie's standout character is Jeff Spicoli (Penn), who has become one of those oft-imitated movie personalities."

Co-starring Phoebe Cates as Linda Barrett, and Judge Reinhold as Stacy's older brother Brad Hamilton, this is a film everyone sees at least once. "Fast Times At Ridgemont High" was a snapshot of southern California teen life in the '80s that feels authentic and has taken on a cult status among multiple generations of teenagers. Seeing the film is almost a rite of passage; an introduction to teen angst and the tendency for teens to rush toward the complications and frustrations of adulthood, rather than slowing down to enjoy those last years of freedom and innocence.

The film wasn't universally liked by critics when it came out in the '80s, but it spoke to teens, and we think that was the director Amy Heckerling, and screenwriter Cameron Crowe's intention (per IMDb). ReelViews said the film, "will always be remembered for one thing: showing respect for and insight into the members of its core audience, something that was as rare in the 1980s as it is today." We couldn't agree more. The film isn't perfect, but it resonated with its intended audience, making it successful commercially. "Fast Times" has a 78% score on Rotten Tomatoes, making it "certified fresh" and worth seeing.

In 1999, Sean Penn secured his second Oscar nomination playing Emmet Ray in Woody Allen's film "Sweet and Lowdown" about a temperamental, unreliable, but unequivocally talented jazz guitarist. Penn's co-star Samantha Morton was also nominated for an Oscar for her role in the film. The film is a mockumentary, with interviews scattered throughout the film where critics talk about Emmet Ray, with Roger Ebert saying in his review, "Emmet Ray is a fictional character, but so convincing in Woody Allen's 'Sweet and Lowdown' that he seems like a real chapter of jazz history we somehow overlooked." 

Of course there is the question of Woody Allen, the writer and director himself, who seems to inspire either adoration or annoyance. Some of us love Allen's films, while others simply do not. But "Sweet and Lowdown" might be the film audiences who generally find Allen neurotic and irritating are won over by. Entertainment Weekly said, "Allen draws a snappy, loose-limbed performance from Penn." Critics certified the film as "fresh" on Rotten Tomatoes with a 77%, and audiences liked it even more.

In 1989, Michael J. Fox and Sean Penn co-starred in director Brian De Palma's film "Casualties of War," as two soldiers during the Vietnam War. The film is a fictionalized version of real-life events Daniel Lang wrote about in The New Yorker, known as the Incident on Hill 192. In De Palma's film, like the articles and book that preceded it, the names have been changed, but the core of the story is intact. While Private Eriksson (Fox) is under the command of Sergent Meserve (Penn), he finds himself at odds with the other soldiers when he refuses to participate after they kidnap, rape and murder a Vietnamese woman (Thuy Thu Le).

This is a heavy and visceral film, Rolling Stone called, "a portrait of hell so harrowing it's impossible to shake." This film isn't for the faint of heart, but it is, unfortunately, a fair representation of the types of abuses that happen at the hands of soldiers to women in occupied territories during war. Roger Ebert gave the film three stars, saying Meserve, "is played by Penn with such raw, focused power that it is easy to see how a weak person would be intimidated by him." Other critics agreed, giving the film 83% on Rotten Tomatoes. "Casualties of War" is a powerful film, but painful to watch.

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"I Am Sam" is one of those polarizing movies critics hated and audiences loved. Sean Penn's performance as Sam Dawson, a mentally challenged man with a low IQ, who lost custody of his 7-year-old daughter, won Penn his third Oscar nomination. Obviously somebody in the Academy enjoyed the film and Penn's performance as much as the audiences who gave it an 86% rating on Rotten Tomatoes. Dakota Fanning is terrific as Lucy Dawson, Sam's sweet and bright daughter, and Michelle Pfeiffer's transformation from an ice queen to an empathetic friend — playing Sam's lawyer Rita — was touching.

Many found the premise of the film problematic, and took offense to Penn playing a man with a challenged mental capacity. Some found the film ablest, and others thought it an unrealistic story with a bad script. But many found "I Am Sam" touching and heartfelt. While some of the criticisms are fair, Sam's friend group felt a little too-cutesy and contrived. The emotional core of the film was what resonated with audiences. It is, after all, a critics' job to think critically about a film, while audiences are freed to take an emotional ride with the characters.

In the 1998 war film "The Thin Red Line" Sean Penn plays 1st Sergeant Welsh, a soldier in the Battle of Guadalcanal. This film has an all-star cast including: Adrien Brody, George Clooney, John Cusack, Woody Harrelson, Nick Nolte, John C. Reilly and John Travolta. Although this is a war movie, it is more about the inner mental and emotional experience of the soldiers during the battle, more than war itself. Written and directed by Terrence Malick, the film has the look of an art-house movie, with gorgeous cinematography. Rob Humanick, with Slant Magazine, said, "in terms of pure artistry, 'The Thin Red Line' continues to dwarf all but a handful of other war films." 

The beautiful lush island juxtaposed with the ugly violence of battle is powerful and jarring. This isn't your average war movie. Gavin Smith of Film Comment called it "a kind of lyric epic poem," and that is the perfect description of "The Thin Red Line." Critics and audiences agree, giving it high ratings of 81% and 80% on Rotten Tomatoes.

Paul Thomas Anderson's "Licorice Pizza" is a coming-of-age story set in the San Fernando Valley in the '70s, about Gary (Cooper Hoffman), a 15-year-old aspiring actor, and Alana (Alana Haim) a 25-year-old woman who he meets at his school's picture day while she is working as the photographer's assistant. Sean Penn joined the ensemble cast in the part of Jack Holden, an actor Alana meets while auditioning for a movie role. This slice of surreal nostalgia was a hit with critics securing a 91% on Rotten Tomatoes and a must-see score of 90 on Metacritic.

The audiences haven't given the film as much esteem as critics (at the time this article was published), but we have a feeling the audience scores will rise as more people see this charming and funny film. Richard Roeper of the Chicago Sun Times said, "'Licorice Pizza' is a visual feast brimming with razor-sharp dialogue, hilarious comedic vignettes, brilliant performances from Cooper Hoffman and Alana Haim as well as the veteran, star-studded supporting cast." We have a feeling "Licorice Pizza" will gain a cult status once it is streaming. This might be one of Paul Thomas Anderson's best films, with Empire calling it, "a thrilling culmination of his talents."

In 2007 Sean Penn wrote and directed "Into the Wild," his most commercially and critically successful foray behind the camera. The film is an adaptation of Jon Krakauer's nonfiction book by the same name. Both tell the story of a young man, Chris McCandless (Emile Hirsch), who, after graduating from college with honors, cut ties with his parents, Walt McCandless (William Hurt), and Billie McCandless (Marcia Gay Harden). Disenchanted with modern life, he gives away his possessions, donating his life savings, before embarking on a cross-country trip that ends tragically in the Alaskan wilderness where he dies.

The Sydney Morning Herald said, "Penn's directing career has been moving towards a major statement and I think this is it," adding, "'Into The Wild' is one of the best films of the year." Others seem to agree, giving the film an 83% score with critics, and 89% with audiences on Rotten Tomatoes. As reported by USA Today, seven years after the film was released, Christopher's sister Carine, who was played by Jena Malone in the film, released a memoir, "The Wild Truth" detailing the abuse Christopher and Jena experienced at their father's hands. Finally revealing what the young man was running from and perhaps why he was so troubled.

In 1995, Tim Robbins wrote and directed Sean Penn and Susan Sarandon in "Dead Man Walking," a film loosely adapted from the memoir of the same name by Helen Prejean. In the film, Sister Helen Prejean (Susan Sarandon), attempts to help death row inmate, Matthew Poncelet (Sean Penn), in a last ditch effort at an appeal, but her role shifts to spiritual advisor when it becomes clear Poncelet will face execution for the crime he claims to have not committed. Penn was nominated for the first time for an Oscar for his performance, and Sarandon won an Oscar (per IMDb). The film was critically acclaimed and commercially successful at the box-office.

Newsweek said, "It's a strong film, made stronger by two terrific performances. Penn's acting has ruthless honesty." Anyone who questioned Penn's talent before this film no longer did after they saw his raw performance. Director Robbins doesn't make Poncelet into a likable martyr, nor does he condemn him. Robbins performs a balancing act, asking the audience to question capital punishment on its own grounds, not on the assumption of innocence. Roger Ebert gave the film a rare four stars, saying "Penn proves again that he is the most powerful actor of his generation," calling the film, "absorbing, surprising, technically superb and worth talking about for a long time afterward." With a 95% critic rating on Rotten Tomatoes, clearly many others thought the film worth talking about too.

In 2008, Sean Penn starred as Harvey Milk, the first openly gay man to hold a public office in the U.S., in director Gus Van Sant's biopic "Milk." The film follows Harvey and his new lover Scott Smith (James Franco) from New York City, where Harvey has lived as a closeted insurance executive, to San Francisco where he opens a camera shop in the Castro. And while in the Castro, Harvey plays a prominent role in making the neighborhood a mecca for gay men and lesbian women in the '70s, ultimately becoming involved in the gay rights movement and politics, finally winning a seat in 1977 on The Board of Supervisors after multiple failed attempts at public office.

Roger Ebert gave the film a rare four-star review, simply saying, "Sean Penn amazes me." The movie is a beautiful tribute to Harvey Milk's legacy and the gay rights movement, and a retelling of Harvey Milk's and Mayor Moscone's (Victor Garber) tragic murders at the hands of Dan White (Josh Brolin). The supporting cast includes Emile Hirsch, Diego Luna and Alison Pill, who are also excellent. But it was Penn's performance that astounded critics and viewers alike, gaining him his second Oscar.

Penn is known for his method-acting, but in this film he completely embodies Harvey Milk. USA Today said the film, "has one of the finest ensemble casts this year and a magnificent, career-topping performance by Sean Penn, who disappears into the title role." Many have called "Milk" Van Sant's best film, and it is certainly Penn's best performance. If you haven't seen it yet, Rotten Tomatoes gave the film a 93% score with critics and an 89% with audiences, suggesting you should watch it soon.