Counting down Brad Pitt's 20 best performances

In a movie dominated by outstanding and unforgettable supporting roles (almost cameos, really) few have endured like Brad Pitt’s Floyd, the slacker stoner roommate to Michael Rapaport’s Dick Ritchie, . The role in and of itself is hilarious: Floyd is the type of guy everyone knows, and not in a good way. But there’s a lovability that comes with the know-it-all grungy stoner who does nothing but wander about and lay in a haze of weed smoke, and Pitt turns this role into a special one. When the film premiered in 1993, Pitt was dipping his toes into odder roles to prove he was more than just a sex symbol (after Johnny Suede and Kalifornia and before Seven and 12 Monkeys). While the decidedly dressed-down role allowed Pitt some forever quotable lines and props, the killer line delivery comes when Floyd, tiring of a smug gangster’s (James Gandolfini) line of questioning, sneaks in the line, “condescend me, man, I’ll fucking kill ya.” It’s just a great, teeny role from one of the best character actors ever. [Don Lewis]

Every once in a while, the world needs a good, sweeping Western, and that’s exactly what the world got in 1994 with this big, emotional, lusciously shot production. Director Edward Zwick locked in a top-notch cast for that includes Pitt, Anthony Hopkins, Julia Ormond, Aidan Quinn, Henry Thomas, Karina Lombard, and Gordon Tootoosis. Pitt is the de facto star, playing Tristan Ludlow, the son of family patriarch Col. William Ludlow (Hopkins) and brother to Alfred (Quinn) and Samuel (Thomas). The Ludlows’ saga encompasses the horrors of World War I, the mistreatment of Native Americans in Montana, the complicated affections of various women, and a couple of memorable encounters with bears. Here, just a couple of years after his breakout in A River Runs Through It, Pitt is in full movie-star mode. The camera loves him—Zwick misses no opportunity to capture Pitt at his sweatiest, long-haired, sun-kissed best. But what makes this a notable entry for our list is that Zwick elicits a powerful, heartfelt performance to match. Tristan experiences love and loss and resignation, and Pitt makes you feel every joy and heartbreak even as you watch and can’t decide what’s prettier, Pitt or the Montana landscape (actually Canada, but, hey, it’s the movies!). [Ian Spelling]

There’s a difference between confident and cocky, and Pitt is someone who can make the distinction effortlessly. Look no further than Robert “Rusty” Ryan in , , and . It’s one of the actor’s most iconic roles thanks to a seamless collaboration with director Steven Soderbergh and, of course, costar George Clooney. A heist expert who’s always low-key having a blast, in part because he’s several steps ahead of everyone around him, Rusty is a character who could skew cartoonishly huge or skeezy.Instead, Pitt turns him into an essential part of a cast worthy of two sequels, cranking his charisma levels to their highest setting and downplaying everything. (In one of the funniest exchanges in Ocean’s Eleven, .) The Ocean’s franchise also provides the prime example of Pitt’s go-to acting trick, a choice that eagle-eyed film buffs may have noticed throughout his decades-long career: stuffing his face with food. Once you see how often Pitt eats in character, you can’t unsee it; with roles like Rusty, you even get the sense he may have constructed the guy around the precise way he chomps down on a steak sandwich. [Jack Smart]

Although Pitt had previously acted with ex-wife Angelina Jolie in the playfully spry action comedy Mr. & Mrs. Smith, it’s his focused work in her third directorial feature that shows audiences new shades from the actor in a performance that’s raw, resonant, and devastating. This ennui-coated, personalized rumination on marital strife set in a French seaside hamlet tells of a husband and wife working through their intense issues: he’s a booze-addled writer attempting to channel his distraught feelings into prose on a page, and she’s a former dancer coping with trauma and grief in destructive ways. Through tidy, astute nuances, Pitt gives us a clear window into his character’s psyche, nimbly vacillating between tough and tender. His debonair, handsomely dressed exterior shows a well-put-together swagger, but it’s the internal portrait he paints that’s truly masterful. Pitt inhabits this role of a broken, lovelorn man frustrated by his wife’s sorrow, physical rejection, and undermining actions with a compelling sense of vulnerability, pulling from a deep well of empathy and grace. His aching desperation and unwieldy angst materializes in the undercurrents of Roland’s actions, sweeping us away in his undertow. [Courtney Howard]

Pitt reunited with Andrew Dominik, the director of The Assassination Of Jesse James By The Coward Robert Ford, for , an atmospheric, moody near-miss. After a poker game involving a bunch of mobsters (led by ) is robbed by a couple of amateurs (Scoot McNairy and Ben Mendelsohn), professional hitman Jackie Cogan (Pitt) is brought in to sort through the events, determine who’s at fault, and mete out something resembling justice, or, more accurately, punishment. Dominik surrounds the actor with several familiar, talented character actors, including James Gandolfini, Vincent Curatola, and Richard Jenkins, and lets Pitt do his thing. And that thing here is, effectively, to underplay Jackie. Reserved, detached, contemplative, smart, and always thinking ahead, Jackie knows when to delegate dirty deeds and when to carry them out himself. That all registers on Pitt’s face and in his eyes, especially when he’s pulling the trigger. And though one can debate whether or not the use of the 2008 presidential election to bookend the film works, Pitt convincingly delivers a pissed-off Jackie’s powerful final words as Obama delivers his victory speech. Hope? Nope. [Ian Spelling]

Pitt had been compared nonstop to Robert Redford for several years already when Redford, in his capacity as director, tapped Pitt for a supporting role in his lush, touching adaptation of Norman Maclean’s novella . The film is early Pitt—he wasn’t 30 yet—so he was neither a superstar nor as confident an actor as he is today. (To put it in perspective, Craig Sheffer was billed above him.) Yet there’s some nice subtlety to his performance here as the hard-drinking, poker-playing, story-breaking journalist and avid fly fisherman whose troubled life is at odds with the film’s gorgeous, bucolic Montana setting. And he’s particularly impressive when sharing scenes with Sheffer, who plays his brother, and Tom Skerritt, who plays their minister father. Redford, wisely, also puts Pitt’s good looks to use. How can a character so angelic in appearance, who literally glistens, be such a mess? [Ian Spelling]

Joel and Ethan Coen’s is a low-stakes spy satire in which a bunch of unintelligent, lovelorn and/or myopic characters cycle through many ill-advised decisions. It’s also the movie that, with his portrayal of gum-snapping fitness instructor Chad Feldheimer, best exemplifies Pitt’s deft touch with “himbo” comedy—and the sheer gleefulness and total dedication with which he tackles dim bulb characters, rivaled among his contemporaries only by costar George Clooney. With his streaked hair, puppy dog energy, and low-information grasp of detail (“Numbers and dates!” Chad exclaims repeatedly, when examining a CD of what he believes to be classified material found on a locker room floor), Pitt breathes full, affectionate life into Chad, who teams up with coworker Linda Litzke (Frances McDormand) to try and extort Osborne Cox (John Malkovich). The role affords Pitt some meme-worthy moments of loose-limbed physical comedy, it’s true. But when Chad finally meets up with Osborne in person, he adopts a whispery spy voice and slips into the dial-up modem equivalent of a secret agent persona. This detail is pure Coen brothers, of course, yet Pitt lets you see the full effort of Chad’s very heavily practiced “character,” and share its utter joy. [Brent Simon]

Among his earliest film roles, Pitt was second-billed to Tom Cruise in the 1994 gothic drama , but only because Cruise’s career at that time had been further solidified than the still burgeoning Pitt. The film’s story is Louis de Pointe du Lac’s to tell, as played by Pitt, recalling his life to a journalist played by Christian Slater. Cruise plays seasoned vampire Lestat de Lioncourt, who dooms Louis to the life of the immortal. While Lestat demands death and sacrifice in order to survive, the morally conflicted Louis can’t bring himself to abide, which causes tension between the two. Pitt is relatively stoic as our narrator, allowing Cruise and a young Kirsten Dunst (the actress was only 11 years old) to chew the scenery around him. When the film ultimately shifts to a two-hander, Pitt’s tender moments opposite Dunst shine. It may not be his most memorable performance, perhaps not even the most memorable performance in the movie (that honor goes to the teeth-gnashing Dunst), but Louis remains significant in the trajectory of Pitt’s career. Audiences then and now can see him hold his own with an at-the-time bona fide star in Cruise. [Brandon Kirby]

At the center of director Terrence Malick’s impressionistic, cosmos-spanning epic lies an authentic portrait of a young boy, Jack (Hunter McCracken), coming of age in 1950s-era Texas. As Jack’s father, Pitt is the very model of mid-century masculinity, with his military-style buzz cut, crisply ironed dress shirts, and high-waisted slacks. And on an interior level, the actor bends his whole being into a stoic rigidity, reflecting a macho adherence to repressing messy emotions. While Pitt’s Mr. O’Brien isn’t stingy with showing affection to his wife (Jessica Chastain) and three sons, he is, like many fathers during this post-war period, a fearsome, sometimes abusive disciplinarian. The hard-edged stripe of manhood that Pitt presents is also connected to eternal human instincts. Within Malick’s profound vision of existence, there are two ways of going through life—the way of nature, and the way of grace. The character’s forceful dominance makes him a representation of the former, but Pitt’s complex performance reveals stray traces of the latter, whether it’s in how blissfully transported Mr. O’Brien is while playing the piano, or in his awestruck face as he studies his newborn son’s tiny feet. It’s a characterization that movingly reminds us that we’re all capable of following the way of grace. [Brett Buckalew]

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]