Sean Penn's 15 Best Film Roles Ranked

Penn gave one of his earliest comedic performances in the bank robbery adventure "Crackers," which follows an unlikely alliance between a group of established thieves and dim-witted retail workers. Weslake (Donald Sutherland) is more or less the mastermind behind the planned heist of a pawn shop, and realizes that his existing crew could use some hired help who knows the location. He recruits Penn's character, the electrician Dillard, who dreams of being a musician.

Dillard's inexperience sticks out like a sore thumb, and Penn is willing to be the butt of many jokes. His failed attempts to install a fake security system only derail the team's plans, and Weslake grows irritated by Dillard's limited attention span. Not all of the jokes in "Crackers" land, but Penn's amusing comic oaf makes it worth watching. It is fascinating to compare the juvenile tone of "Crackers" with Penn's more serious work.

"I Am Sam" is a flawed film. The depiction of a disabled character is earnest, but the film frequently descends into melodramatic territory, and can be manipulative with its heartwarming message. The film itself was divisive among critics, audiences, and disability activist groups, but Penn's performance was acclaimed. Despite the controversy, Penn was still nominated for an Academy Award for best actor.

Sam Dawson (Penn) has the mental capacity of a child, and raises his daughter Lucy (Dakota Fanning) on his own. Sam's ability to care for a girl whose intelligence will soon surpass his own is called into question, and he's threatened with losing custody. The cynical lawyer Rita Harrison Williams (Michelle Pfeiffer) only takes his case to improve her public reputation, but gradually grows charmed by Sam's earnest love of his daughter. Penn is very respectful with his performance; he gives Sam a personality without stigmatizing his childlike behavior.

Films that tackle the Iraq War and conspiracies inside the Bush administration can be very powerful, but often they're unable to capture the scope of the conflict without simplifying the details. 2010's "Fair Game" is one of the better examples, as its premise is unique and its characters face realistic consequences after being labeled public enemies by the media. CIA agent Valerie Plame (Naomi Watts) learns about a US investigation into yellowcake uranium in Niger that conflicts with official reports. Unable to stay silent, her husband Joseph Wilson (Penn) leaks the information to the press.

What's brilliant about "Fair Game" is that it examines the political issues through how they impact an individual marriage. Plame and Wilson see their entire life uprooted; they're hounded by interviewers, scolded by their friends, and don't feel safe in their own home. Valerie is furious at her husband for leaking the report without her permission, which strains their relationship, and Penn and Watts take great pains to make their conflict feel realistic.

Penn first collaborated with Terrence Malick as just one of the many great actors in the stacked ensemble cast of "The Thin Red Line." The grand World War II epic details the combat in the Pacific Theater during the final Guadalcanal Campaign, and Malick explores the various individual stories of heroism in the American companies. The storyline featuring Penn's character, First Sergeant Welsh, opens the film amid preparations to reinforce a critical canal.

Welsh's men intercept the deserter Private Robert E. Lee Witt (Jim Cavaziel), who has abandoned his post to live with Malaysian natives on the shoreline. Welsh plays down his authority, but lets Witt know that he's the only friend he has. He commands Witt to carry a stretcher for the rest of the war. It's a perfectly grim exchange that sets the right tone for the rest of the film.

Penn's pursuit of challenging dramatic roles would become one of the hallmarks of his career, so in retrospect it's surprising that his star-making turn came in the 1981 high school sex comedy "Fast Times at Ridgemont High." An adaptation of a series of high school stories by Cameron Crowe, Amy Heckerling's directorial debut is an insightful and hilarious look at the primal desires of California adolescents. Penn generally seems intelligent during his performances, but his intellectual qualities are completely absent from the dim-witted stoner Jeff Spicoli.

Spicoli's passions are as simple as surfing and partying, and he's easily the scene-stealer in a film that features many future stars. Spicoli essentially interrupts the main storyline with his goofy antics, but is forced to reckon with his own obliviousness when the art teacher Mr. Hand (Ray Alston) makes it his goal to get Spicoli expelled. Their heart-to-heart at the film's conclusion is surprisingly respectful, and the only serious moment featuring Spicoli. Compared to other high school comedies, "Fast Times At Ridgemont High" has aged very well, and it's a performance Penn is still proud of — he recently appeared in a live reading of the original script for charity.

Penn's dedication to authenticity made him a perfect choice to play a key historical figure whose impact is still felt today. Gus Van Sant's 2008 biopic "Milk" tells the groundbreaking story of Harvey Milk, the LGBTQ rights advocate who became the first openly gay individual elected to office in California. Milk faced discrimination throughout his entire life, particularly during his tenure in San Francisco. Penn earned a second Academy Award for best actor for his sensitive, thoughtful performance.

The film frames its account around a record Milk makes only a week prior to his assassination at the hands of the homophobic city supervisor Dan White (Josh Brolin). Milk recalls his early days as an activist in the San Francisco community, and his passionate romance with Scot Smith (James Franco). The leadership he shows early on foreshadows his later achievements, but Penn doesn't treat Milk as a superhero. He shows that Milk is still a fallible human, one who makes both enemies and friends through gradual political gains. By treating Milk as a three-dimensional character and not a figurehead, Penn allows the viewer to appreciate his actual purpose, making him more than a list of historical notes. As a result, his tragic end is even more heartbreaking.

In the same year that he was showered with critical praise for his career-defining role in "Mystic River," Penn delivered another awards-worthy performance in Alejando Gonzales Inarritu's heartbreaking drama "21 Grams." Inarritu is rarely interested in pleasing his audience with a satisfying ending or characters with clearly defined morals, and his outlook on humanity is often bleak. "21 Grams" confronts challenging themes about recovering from loss and accepting death, and is told via a nonlinear structure that may initially seem confusing. However, it's consistently gripping thanks to the phenomenal ensemble, and in it Penn delivers one of his most honest performances.

Paul Rivers (Penn) is a brilliant mathematician, but he's hamstrung by a debilitating illness that slowly depletes his cognition. He's eager to return to a semblance of normality, but is caught in a longstanding argument with his wife Cristina (Naomi Watts), who wants to have children through artificial insemination. Cristina is also obsessed with finding the ex-con Jack Jordan (Benicio del Toro), who spent years in prison for a hit-and-run accident that killed her ex-husband and their children.

As Cristina pushes him to help her get revenge, Paul is forced to question what the best course of action is. He's struggling through his own illness, but he also knows that the initial tragedy is what introduced him to Cristina. Inarritu asks fascinating questions about whether vengeance is ever truly satisfying; Penn generates sympathy as he's roped into the uncomfortable scenario.

"Mystic River" is a heartbreaking depiction of a tragedy at the heart of a seemingly normal small town, and one of the greatest American films of the 21st century. Clint Eastwood's slow, methodical direction has produced mixed results throughout his long career, but with "Mystic River," Eastwood's deliberate pacing escalates the latent tensions within a Boston community haunted by generational family conflicts. 

Jimmy Markum (Penn), Dave Boyle (Tim Robbins), and Sean Devine (Kevin Bacon) were childhood best friends, but a shocking tragedy in which Dave endured unthinkable abuse has haunted them well into adulthood. Dave is now a likeable, quiet family man who attempts to raise his son in a nonviolent environment, and Devine is a police detective who rarely contacts his former friends. However, Jimmy has earned a fearsome reputation, and rumors persist about the crimes he may have been involved with.

The shocking death of Jimmy's teenage daughter Katie (Emmy Rossum) brings the trio together again. Jimmy is beyond heartbroken, but his mourning is quickly followed by a need for vengeance. He questions Sean about the details of the case, and becomes obsessed with Dave upon learning that he's a suspect. Jimmy becomes convinced of Dave's guilt, and is willing to go to extreme circumstances to achieve justice.