Counting down Brad Pitt's 20 best performances

By the late 1980s, Pitt was racking up numerous, if undistinguished, acting credits on shows like the daytime soap Another World and the nighttime soap Dallas. Then came Ridley Scott’s 1991’s feminist road movie, Thelma And Louise. The part of bank robbing drifter J.D. wasn’t big, but it was a crucial and potentially star-making role. Thank goodness the part went to … Billy Baldwin. And when Baldwin dropped out upon booking Ron Howard’s Backdraft, thank goodness the part went to … Grant Show. When Show couldn’t get out of his TV deal, Scott and the producers settled on Pitt, launching his movie career. With his laid-back sexuality, thick and charming Southern accent, and 0% body fat, Pitt was the perfect choice for a character whose primary job is to help Thelma (Geena Davis) reclaim her sexuality after years in a bad marriage. Anyone with a pulse will always remember the scene where a shirtless, ab-tastic Pitt holds Thelma’s hairdryer like a gun and says, “If nobody loses their head, then nobody loses their head.” Oh, but America absolutely lost its collective head, making Thelma And Louise the last time anyone in Hollywood would settle for Brad Pitt. [Mark Keizer]

How cool is Pitt? So cool that in he plays an astronaut whose heartbeat never goes above 80 BPM, no matter how stressful the situation he’s in. Even when he goes on a space expedition to find his long missing father (Tommy Lee Jones), or when he faces death and world extinction. However, this is no disaster movie, more of a character study about a man dealing with daddy issues—in outer space. Pitt gives a quietly stunning performance as a man who doesn’t show much emotion; the actor finds a way to make reticence look highly emotional on screen. For most of the running time we see only his face, and on that face we are able to read all that the character is going through. The performance is so immense, in fact, that director James Gray (or the studio) should’ve trusted their star to convey the sparse script without voiceover narration deployed. This is Pitt at his most weathered, carrying the weight of the world on his shoulders, yet remaining immensely alluring. [Murtada Elfadl]

The beginning of a hideously beautiful partnership with David Fincher, owes the preservation of its severe downer ending to Pitt, who refused to do the film otherwise. Many blockbusters have ripped off the film’s second act turn, with a villain who turns himself in as part of a larger plan. Few—save the Saw sequels, which owe much of their existence to an audience primed by Fincher—have the guts to go through with the final execution, in which Pitt’s naive hero David Mills is unalterably corrupted and destroyed as a human being.Pitt and then-girlfriend Gwyneth Paltrow play an idealistic young couple on the verge of becoming jaded; Fincher tosses them into hell as Mills investigates a series of gruesome murders based on the seven deadly sins. Morgan Freeman’s Somerset serves almost as the Batman of this gothic city, with the right amount of cynicism to survive and the determination to keep trying to do good anyway. Idealism is the ultimate pitfall, pun intended: it drives killer John Doe (Kevin Spacey) deep into evil, and renders Mills a dupe of the master plan. The real-life Pitt doesn’t look like anybody’s loser, which heightens the impact of this gory tale. If he can fall for it, what hope do you have? Or anyone else? [Luke Y. Thompson]

For years, Quentin Tarantino had discussed making a World War II movie, sometimes hypothetically starring Adam Sandler or Sylvester Stallone. When he finally cast Pitt, and named the film after Enzo G. Castellari’s Italian Dirty Dozen rip-off, some viewers may have assumed would be an action movie. Instead, it’s a massive redirect. After Pitt’s Aldo Raine gives his crew an inspirational speech about collecting “Gnat-see” scalps, the movie settles into a story of interrogations and tense conversations, mostly involving theater owner Shosanna (Melanie Laurent) and dogged Nazi Hans Landa (Christoph Waltz).While much of the film revolves around scenes of clever characters feeling each other out, Pitt’s Raine remains a blunt instrument, so unsubtle as to not even fake an undercover accent. It’s a meta joke on the idea of classic movie stars not being chameleons; it’s also, at every stage, a subversion of expectations regarding what a war movie hero is supposed to be. In the end, he must save the villainous Landa rather than slay him, but not before leaving a nasty souvenir. On the one hand, it’s yet another Pitt role that subverts his natural movie star looks and charisma. But it’s also Pitt having fun pretending to be in the kind of John Wayne-like cowboy hero role he’s too smart to ever take fully seriously. [Luke Y. Thompson]

As much as Pitt is lauded for his acting, he’s also an Oscar-winning producer. He launched his production company, Plan B Entertainment, in 2001 with Brad Grey and Pitt’s then-wife, Jennifer Aniston, before assuming sole ownership in 2005. Two years later, Pitt received both starring and producing credits on . The film, directed by Andrew Dominik (of the upcoming Marilyn Monroe biopic, Blonde), is a moody and languorous 160-minute essay on the perils of hero worship that Pitt, as good producers will do, had to protect from a studio that thought they were getting a standard shoot-’em-up Western.Pitt plays the famous outlaw at the end of his bank robbing career. “All America thinks highly of me,” Jesse says with the hard-earned wisdom of someone who’s come to terms with a betrayal that he’s too weary to try and stop. Whether Pitt saw a little of himself in James, a man who carries the burden of being a living legend and doesn’t much like it, we can’t say. We do know that Assassination is the first film Pitt would both appear in and be given an onscreen credit as producer, a feat he’s repeated numerous times, including in two Best Picture Oscar nominees, Moneyball and The Big Short, and one Best Picture Oscar winner, 12 Years a Slave. So not only can Brad Pitt act, he can also pick great material to produce. [Mark Keizer]

A lavish, disarmingly sincere throwback, was unfairly maligned at the time of its release, but is now widely admired. Perhaps viewers just needed time to recognize and embrace its anachronistic virtues. Director Martin Brest’s film is driven by sophisticated wit, opulent fashions, powerfully emotional melodrama, and, of course, a megawatt movie star turn. When we first see Pitt, he’s at his most impossibly charismatic, flirting with an immediately smitten doctor, Susan (Claire Forlani), at a coffee shop. But Death quickly takes control of this café denizen’s body and asks Susan’s media mogul father (Anthony Hopkins) to show him what life’s all about. Playing this specter in a human’s body, Pitt’s dazzling blue eyes lock into a fixed, rarely blinking gaze while his vocal delivery coldly stiffens. Gradually, his robotic demeanor loosens up as “Joe Black” (his alias) is overtaken by life’s pleasures, evincing a hilariously childlike love for peanut butter and a deep romantic affection for Susan that make his eyes fill with tears. When it comes time for Joe to leave Susan, Pitt’s vulnerability proves that heartbreak lies at the core of being human. The viewer’s eyes might fill with ample tears as well. [Brett Buckalew]

Despite receiving an Oscar nomination for best actor—one of 13 for —this performance is seldom regarded amongst Pitt’s best, perhaps because of the heavy old age makeup and CGI required to tell this story of a man aging backwards. The visual transformation might eclipse the performance, but look deeper and you’ll see the grounded humanity Pitt brings to the role. He’s somehow utterly believable playing someone born old with an innate and wise understanding of life. And when the film shifts to showing him in his natural visage as Button de-ages, he hits a different gear. Both the film and performance slow down to show us the romance with his true love Daisy, played by Cate Blanchett. They are “,” two people who have known each other all their lives, finally allowing themselves to acknowledge their love, knowing time is slipping away. Their chemistry is off the charts, and they show us why we love to look at movie stars. This David Fincher-directed story might be one of grandeur, but Pitt’s performance wrings genuine emotions in the midst of all the hoopla. [Murtada Elfadl]

At the risk of breaking the first rule: when somebody says is their favorite movie, there are two options. One is that they have a dark sense of humor, appropriately cynical worldview, and a music collection that includes the Pixies and Nine Inch Nails. The other is that they are one of the worst people in the world. As the extremely handsome, fit, intelligent, dangerous (and, crucially, non-existent) cult leader Tyler Durden, Pitt delivers a performance that appeals to both. The proto-MAGA types long to follow someone like him, an ostensible bomb thrower who’s really just another cult leader, just like a former president we all know. Those with a nose for irony see the double standard, and take to heart the reality that he’s actually the projection of an antisocial, mentally ill loner (Edward Norton) so numbed by consumerism that he needs a good punch in the face. He’s also potentially messing with the movie we’re actually watching, splicing in porn frames and subliminal pictures of himself. At the time an A-lister who seemed to have it all, Pitt perfectly portrayed both that image of what every man wanted to be, and the flipside—that such people either don’t exist, or have far more of a dark side than you know. Now if only we could persuade the real-life analogs of Project Mayhem that that’s the case. [Luke Y. Thompson]

For a while, Pitt was considered a shoo-in for the Best Supporting Actor Oscar thanks to his work in . Though he eventually lost to his future Se7en costar Kevin Spacey, he won the Golden Globe and turned many heads as Jeffrey Goines, a mental patient turned eco-terrorist. Cast against type and director Terry Gilliam’s initial wishes (he had apparently wanted Jeff Bridges), Pitt wore brown contacts to make his naturally blue eyes look unusual, checked into a psychiatric hospital for a day, and stopped smoking in order to convey the right level of hyperactive energy. His role is ultimately a misdirection—time traveler Bruce Willis believes he’s the guy who will unleash a deadly virus that will send future humans underground. But in a Gilliam movie, audiences should know better—the crazy ones are usually right, and the seemingly benevolent authority figures are generally evil under the surface. It’s also the craziest characters that people remember in a Gilliam film. With Willis playing the painfully earnest martyr figure, Pitt—who’d become a major star between being cast and the film actually coming out—steals the show by contrast. Not just to his costar, but to everything he’d ever done up to that point. [Luke Y. Thompson]

Over the course of his celebrated career, Pitt has embodied many “golden god”-type roles—even Achilles. So casting him as an ambivalent underdog seems on a certain level perverse. But stands as one of the actor’s most indelible performances. Pitt stars as Billy Beane, whose unfulfilled promise as a baseball player informs his perspective and values as general manager of the Oakland Athletics. Masterfully adapted by Steven Zaillian and Aaron Sorkin from Michael Lewis’ nonfiction book, director Bennett Miller’s film chronicles Beane’s attempt, coming off a crushing loss the season before, to pivot and trim costs while still fielding a competitive team for 2002. Pitt’s performance is shot through with an affecting melancholy—the mien of a man burdened by the impact of unpopular decisions he nonetheless believes to be right. He balances, often within the same scene, intense self-questioning with a doggedness of spirit. This tack is ever-present, but most entertainingly manifested in Beane’s first meeting with old-guard scouts, where he attempts to explain to them the then-unconventional use of advanced analytic principles, as well as a series of increasingly contentious power struggles with manager Art Howe (Philip Seymour Hoffman). Most notably, though, Moneyball makes masterful use of Pitt’s special gift with silences and nonverbal reactions, beautifully showcased in sequences where Beane listens to his daughter (Kerris Dorsey) play guitar, or celebrates his team’s 20-game win streak in private. Beane wants deeply to win in small-market Oakland so his break from the status quo will mean something. And Pitt’s quietly towering portrayal helps take “just” a sports tale and make it something epic—an engrossing rumination on American capitalism, as well as modern masculinity. [Brent Simon]