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Not every A-list actor has a filmography that lives up to their status. Brad Pitt is an exception, having starred in some of the best films of the past 30 years through his work with auteur directors like David Fincher, Quentin Tarantino, and the Coen brothers. He’s also been an awards magnet: Between producing and acting, he’s earned seven Oscar nominations, winning Best Picture as a producer on 12 Years a Slave (2013) and Best Supporting Actor for his performance in Once Upon a Time in Hollywood (2019).
Having appeared in more than 60 feature films — and with his newest movie, F1, now in theaters — Pitt’s career isn’t the easiest to catch up on if you’re a completist. Thus, we’ve narrowed down the list to 14 of our favorites, the films that best represent Pitt’s indelible screen presence as a movie star.
12 Monkeys (1995)
Phillip Caruso
Pitt won his first Golden Globe and earned his first Oscar nomination for his supporting role in Terry Gilliam’s science-fiction time-travel thriller. He plays Jeffrey Goines, an unpredictable, ranting psychiatric patient in a dystopian facility who happens to be the son of the world’s premier virologist–turned–aggressive social activist. The throughline of the film involves prisoner James Cole (Bruce Willis) traversing time to gather more information about the onset of a viral outbreak that killed billions.
A young Pitt delivers a performance with varying degrees of composure and erratic behavior, exposing his bare bottom and tearing pillows as he remains unfazed by disturbing actions, such as Willis’ character swallowing a spider alive. More details about Jeffrey’s motivations are revealed while James jumps between timelines. As Pitt’s character evolves, so does his mission, and it isn’t until the final act that the audience understands Jeffrey’s scope of involvement in the catastrophic outbreak. —Derek Scancarelli
Ad Astra (2019)
Francois Duhamel/Fox
This thoughtfully crafted sci-fi drama may be about an astronaut traveling through the vastness of outer space, but its themes are much more intimate. Set in the 22nd century, Pitt stars as Roy McBride, a man tasked with finding his long-lost father, who had previously traversed space in search of alien life, which now threatens Earth’s survival. Naturally, the trip to the outer reaches of the galaxy is a perilous one, made even more complicated by Roy’s conflicted feelings over his father abandoning him all those years ago.
Ad Astra was released the same year as Once Upon a Time in Hollywood, and where his Oscar-winning role shows his undeniable movie star charisma, the former suggests the thoughtfulness and subtlety of a journeyman actor. Through his haunted expressions and plaintive voice-over, Pitt paints a compelling picture of a man still grappling with his past and confronting an unpredictable future. —Kevin Jacobsen
The Assassination of Jesse James by the Coward Robert Ford (2007)
Warner Bros.
Pitt is exceedingly well cast as the infamous outlaw Jesse James in this revisionist Western masterpiece. As the film title suggests, this is less about what happened that fateful night in 1882 so much as how it happened, tracking the psychological unraveling of James and his increasingly fraught relationship with his fellow gang member, Robert Ford (Casey Affleck).
Affleck got most of the critics’ attention — including an Oscar nomination — for his nuanced performance of a complicated man, but Pitt is just as excellent as he nails James’ growing insecurities bubbling underneath the surface of the magnetic gang leader. However, Pitt didn’t go entirely unrecognized for his layered turn, winning the Volpi Cup for Best Actor at the 2007 Venice Film Festival. —K.J.
Burn After Reading (2008)
Macall Polay/Focus Features
No stranger to outrageous ensemble casts, Pitt’s performance in this Coen brothers dark comedy thriller stands out even while he’s among a bevy of fellow Hollywood heavyweights, including George Clooney and Frances McDormand. Pitt plays Chad Feldheimer, a gum-chewing, frosted-tipped personal trainer who navigates the world with a sense of childlike wonder that exists in complete dichotomy with the plot of the film. After discovering a compact disc with allegedly leaked CIA documents, Pitt and McDormand’s characters thrust themselves into a world of love affairs, murder, and utter confusion.
Despite the high stakes and casual violence of the film, Pitt’s character remains giddy as he frolics, dances, and snaps. He fist bumps on the treadmill and drinks orange juice while extorting a federal agent by phone. Burn After Reading delivers Pitt in rare form: a bumbling blockhead who loves berry blast smoothies and sports an iPod strapped to his arm. —D.S.
The Curious Case of Benjamin Button (2008)
Merrick Morton/Paramount
Perhaps the most peculiar character in Pitt’s filmography is his title role in The Curious Case of Benjamin Button, his third project with David Fincher. Loosely based on a short story by F. Scott Fitzgerald, the film tells the tale of Benjamin Button, who is born with the appearance and strength of an elderly man and ultimately ages backward into infancy. Benjamin’s journey begins in 1918; over the years, he navigates his condition, historical milestones, and romance with his childhood friend and lifelong partner, Daisy (Cate Blanchett).
Pitt’s performance in the movie, coupled with CGI and makeup, makes for a role with a variety of sub-characters built in. Not only did he perform as the same person at different ages, but, at each of those ages, he was inversely represented physically. The precision and focus to pull off such a premise cannot be overstated. —D.S.
Fight Club (1999)
Everett Collection
Based on Chuck Palahniuk’s 1996 novel of the same name, David Fincher’s Fight Club is arguably Pitt’s most iconic and recognizable work, as the character of Tyler Durden has transcended film into the general cultural consciousness as a symbol of anti-capitalist-establishment enlightened masculinity. Celebrated by some as gospel and criticized by others as pseudo-intellectual, the split-personality meanderings of Pitt and his counterpart — played by the incredible Edward Norton — have endured the test of time.
As Tyler Durden, Pitt struts with a cigarette in his mouth, rocking his sunglasses and trademark jackets. The hyper-macho, wildly sexual bare-knuckle brawler perfectly juxtaposes Norton’s buttoned-up, worker-bee mentality. As the two explore the curious nature of their relationship and the violent underground fighting ring that brought them together, Pitt delivers one unforgettable scene after the next, cementing that Tyler Durden may long be held as the actor’s most beloved role. —D.S.
Inglourious Basterds (2009)
Francois Duhamel/The Weinstein Company
In Quentin Tarantino’s sprawling World War II-era fantasy, Pitt leads an elite crew of Jewish American soldiers through German-occupied France with one clear mission: to kill Nazis. Playing Lt. Aldo Raine, an ex-moonshiner from Maynardville, Tenn., the no-nonsense leader tells his squad that they should each deliver him 100 Nazi scalps or die trying. Raine, a man of the Great Smoky Mountains, goes by the nickname of “Aldo the Apache.”
Pitt’s character doesn’t mince words. He has a clear distaste for the Third Reich, often smack-talking their troopers’ affinity for sauerkraut and schnitzel before carving a Swastika into their foreheads. Perhaps the most entertaining image of Lieutenant Raine is in the film’s final chapter when the all-American boy cleans up in a white tuxedo and fails miserably at presenting himself as stuntman Enzo Gorlomi — brashly tossing out Italian fragments in his Tennessee drawl. —D.S.
Interview With the Vampire (1994)
Francois Duhamel
Any film that includes Pitt slicing flying, flaming vampires with a massive scythe is worth a watch. Complete with a ponytail, fancy suit, and pale face, Pitt’s character, Louis de Pointe du Lac, details his life as a man — and vampire — to a journalist (Christian Slater) in this gothic horror classic. Based on Anne Rice’s novel, the film was arguably what helped propel Pitt into superstardom.
Told through flashbacks from the current day to the 1700s, the film details Louis’ story as a man who lost his infant and wife during childbirth. Wallowing in his depression, Louis is attacked by Tom Cruise’s Lestat de Lioncourt, a Parisian vampire transplant. Louis later submits to Lestat’s offer to live “free from sickness and death” as a vampire by drinking the latter’s blood. Ultimately, Louis is portrayed as a broken man whose regret is the only semblance of humanity he retains. —D.S.
Meet Joe Black (1998)
Phillip V. Caruso
Pitt stars as…Death. Operating under the pseudonym of “Joe Black,” the character is quickly revealed as, indeed, the human embodiment of death, temporarily perusing Earth as he prepares to take media mogul William Parrish (Anthony Hopkins) to the other side. A devilishly handsome grim reaper, Pitt first appears as a different identity: a quick-witted hunk who enchants the mogul’s daughter in a diner before they bid farewell. It’s not long before a tragic accident replaces the young man’s soul with the spirit of Death.
Pitt’s performance is dramatic but is complemented by a disarming levity. New to the human form, Death becomes obsessed with peanut butter. He marvels at the wheels on an office chair and speaks with no filter. It has some unexpectedly hilarious moments, but, in short, Meet Joe Black is a compelling film because it’s about mortality, posing some of life’s great existential questions. —D.S.
Moneyball (2011)
Melinda Sue Gordon/Columbia/Sony
Based on Michael Lewis’ best-selling book that provides an account of the Oakland Athletics’ 2002 season, this stirring sports drama details the strategy implored by the team’s general manager Billy Beane (Pitt) and assistant GM Peter Brand (Jonah Hill) to redevelop the way a Major League Baseball team is constructed both financially and philosophically.
In Pitt’s performance, his calm in the face of enormous risk speaks louder than a ferocious loudmouth ever could. Billy and Peter systematically built a game-winning team off of statistics and budget, rather than investing the entire franchise’s finances into players who were flashy, self-centered, or individually successful. As Billy explains to his team, the two acted as card counters who were ready to get back at the casino — or teams with astronomical budgets and star power. And perhaps the funniest quirk of Pitt’s character, he didn’t ever watch the games. —D.S.
Once Upon a Time in Hollywood (2019)
Andrew Cooper/Columbia
Tarantino’s ninth film transports audiences back to late-’60s Los Angeles, where fading Western star Rick Dalton (Leonardo DiCaprio) is struggling to find his way forward in an ever-changing landscape. His stunt double, Cliff Booth (Pitt), meanwhile, is the calm, collected, classic car-driving Everyman who has no issue climbing up on the roof to get his hands dirty. And his performance was much appreciated, as Pitt took home an Oscar for Best Supporting Actor.
When Pitt first meets Al Pacino’s character in the famous Musso & Frank Grill on Hollywood Boulevard, he’s sitting at the bar in a denim jacket, crunching on a stalk of celery and twirling it through his Bloody Mary, smiling and cool as a cucumber. That’s a pretty good metaphor for Cliff Booth, who is equal parts suave and badass. Of course, the flick also includes a good old-fashioned brawl and beatdown delivered by Pitt himself. —D.S.
A River Runs Through It (1992)
Everett Collection
In this novella-inspired, Montana-set film, Pitt plays Paul Maclean, the son of a reverend and younger brother of academic Norman (Craig Sheffer). The movie — directed by Robert Redford — is a beautiful slice-of-life vignette, complete with a story of family, companionship, love, and loss. Paul, a young journalist and beloved son, has an alcohol addiction that bleeds into his everyday life, which leaves his brother helpless as he observes the dangerous scenarios his little brother habitually thrusts himself into. Pitt’s character is successful, but is all too familiar with fist-fights and jail cells.
But there is one place Paul finds his inner peace: fly fishing on Missoula waters. Indulging in their family pastime, the Macleans find reprieve from their troubles and tragedies while knee-deep in the Blackfoot River. A River Runs Through It showcases Pitt’s early acting chops — no chic mystique or explosions necessary. —D.S.
Se7en (1995)
Everett Collection
Like Fight Club and The Curious Case of Benjamin Button, Se7en is also directed by David Fincher and is widely regarded as the source of one of the most intense roles of Pitt’s career. As the story goes, a week outside of retirement, Detective Somerset (Morgan Freeman) is ready to step away from police work. As he’s showing young Detective Mills (Pitt) the ropes, he’s given a unique case as a parting gift: a serial murderer is utilizing the seven deadly sins as a theme in his killings.
The slayings are particularly grisly and not for the faint of heart. Take, for example, the first victim portrays gluttony: a man with obesity is force-fed literally to death via hemorrhage. It’s a twisted film, and Pitt’s performance is powerful, notably crescendoing in the final act, when the killer leads the detectives into the desert. They locate a cardboard box with nefarious content, resulting in Pitt’s famed scream, “What’s in the box!?!?” —D.S.
Snatch (2000)
Everett Collection
Taking place in the rough-and-tumble world of British organized crime, gambling, and underground boxing, this Guy Ritchie crime comedy follows a grifter named Mickey O’Neil (Pitt) who finds himself at the center of the blowback from an 84-karat diamond heist, a series of failed fight setups, and murder by arson. A cheeky troublemaker with the gift of gab, Mickeyl’s tattooed torso and penchant for gold jewelry perfectly complement his physique: that of a bare-knuckle boxing champion. Mickey demonstrates quickly that he’s more than just aesthetic, as he tosses a man through a wooden gate in an exhibition of raw power.
Complete with a leather fedora, mustache, and cigarette hanging from his mouth, Mickey is ready to swindle you for whatever you’re worth. A brutish warrior who loves his mother dearly, Pitt’s character is focused on providing for his family and seeking vengeance when harm is done in his own backyard. —D.S.
