Best Brad Pitt Movies Ranked

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Best Brad Pitt Movies Ranked

Between Once Upon a Time in Hollywood and Ad Astra, Brad Pitt is having a hell of a 2019. You could call it a Bradissance or you could just call it Brad Pitt being Brad Pitt. Looking back at the last three decades of movies, even Pitt’s misses are still watchable just because you’re seeing this extremely charming and attractive man on screen. But, given that he’s cutting back on acting, we’re entering a terrifying new era with a lot less Pitt in the movies. That just means to get our full fill of this beautiful guy, we’re going to have to go back and re-watch his best roles. And, to be honest, who doesn’t want to do that?

20) Troy (2004)

The real star of Troy is Brad Pitt’s naked ass, but that’s another article for another day. As a film, Troy is hot garbage, a bloated swords and sandals epic that sucks everything glorious out of The Iliad. What saves it is Pitt, whose Achilles is pouty, churlish, and improbably draped in puka shell necklaces. Pitt has never looked better than he does in Troy, all tousled blonde hair and washboard abs slathered in an oil slick’s worth of body oil. Chief among Troy’s countless egregious revisions of classical mythology is the choice to nix the pivotal scene where Achilles is discovered living as a woman in order to avoid going to war, depriving us of Pitt in ancient drag. Failures of imagination aside, only Pitt could inhabit the legend of Greece’s golden demi-god, bringing virility, tenderness, and movie star grandeur to a part that would overwhelm a lesser performer. —Adrienne Westenfeld

19) Thelma and Louise (1991)

Albeit brief, Brad Pitt’s performance in Ridley Scott’s Thelma and Louise was an early turning point in his career. When you look at the leading cast members, Pitt’s name doesn’t even make the movie poster. Only in the film for about seven minutes, Pitt plays a sexy grifter named J.D. who happens to charm Geena Davis and steal her life savings after a night of sweet loving making. Classic Brad. The short stint cemented Pitt as a Hollywood sex symbol and helped to launch him into bigger films in the years to come. While films like Interview with a Vampire and A River Runs Through It may seem like the moment that Pitt’s rocket took off, make no mistake—it was Thelma and Louise that acted as the spark. — Justin Kirkland

18) The Big Short (2015)

Brad Pitt also produced this Adam McKay Vox-explainer of the housing bubble implosion in the late 2000s. In the Oscar-winning The Big Short, Pitt has a supporting role as Ben Rickert, a retired Wall Street trader who predicts the coming financial collapse. As McKay has said, Pitt turned up to set 20 pounds heavier with a “Ken Burns hairstyle,” and even left the tag on his tie to make it look like he’d bought it at the airport. —Matt Miller

17) Snatch (2000)

This was an era where Brad Pitt took off his shirt and either got his ass kicked or kicked someone else’s ass. Between Snatch and Fight Club, the turn of the century was a gritty time for Pitt. And Snatch remains one of Pitt’s most beloved roles as a bare-knuckle boxer in Guy Ritchie’s stylish and frenetic heist film. You’ll need subtitles to really understand what the hell he’s saying with what’s either his best or worst accent in a movie. Either way, it’s pretty unforgettable. —Matt Miller

16) Interview with the Vampire (1994)

Interview with the Vampire isn’t even remotely close to Brad Pitt’s best movie—really, his newly-bitten vampire Louis de Pointe du Lac looks somewhere between confused and constipated in every scene—but it’s on this list for one gothic castle-sized reason. Pitt somehow, barely managed to hold his own against Tom Cruise—who I’m pretty sure actually thought he was the rabid vampire Lestat de Lioncourt during filming, hammered off the blood of swamp creatures and zipping around Spanish Louisiana like a raccoon with superspeed. I mean… how the hell do you keep a straight face when Tom freaking Cruise is, with both hands, squeezing a rat’s guts into a wine chalice? —Brady Langmann

15) True Romance (1993)

Brad Pitt’s total screen time in True Romance amounts to only a few minutes (you can watch most of it here), and yet his turn as über-stoner Floyd remains one of his most memorable—and beloved movie moments. Pitt reportedly sought out his small part in Tony Scott’s film (penned by Quentin Tarantino, and released a year after Reservoir Dogs), apparently feeling a strong connection to the role of a twenty-something who cares only about sitting on the couch and watching TV, drinking beer, and taking enormous hits from his honey bear bong. Pitt’s goofy, blissed-out spaciness is wholly authentic (his lines are largely improvised), and elicits considerable laughs during his final encounter with a gang of gunmen to whom Floyd, like any decent host, offers a hit. Best of all, though, is his conversation with James Gandolfini’s smiling gangster, which concludes with the good-natured smoker—blunted beyond belief, but sharper than he appears—muttering angrily to himself, “Don’t condensend me, man. I’ll fucking kill ya, man.” — Nick Schager

14) Killing Them Softly (2012)

Re-teaming with his Jesse James director Andrew Dominik for another evocative tale of American criminal enterprise, Pitt once again strives for the mythic in Killing Them Softly, albeit here in a modern guise. Rarely has the actor benefited from an entrance as stylish as the one bestowed upon his hitman, Jackie Coogan, who drives into town for his next job set to the sound of Johnny Cash’s “The Man Comes Around.” While Coogan may not decide, per his theme song, who to free and who to blame, he nonetheless comes across as a biblical force, tasked with balancing the underworld’s illicit scales by offing two low-rent thugs stupid enough to hold up a mob card game. With slicked back hair and a neatly trimmed goatee, Pitt is remarkably restrained, allowing subtle gestures and changes of expression to reveal the burdens he’s shouldered, the regrets he still carries, and the mileage on his odometer. — Nick Schager

13) Ad Astra (2019)

It’s difficult to say goodbye for Pitt’s astronaut Roy McBride, who’s charged with traveling to space to send a message to his long-lost explorer father (Tommy Lee Jones) in James Gray’s Ad Astra. Narrating his character’s troubled inner thoughts as he embarks on this perilous mission, Pitt is a subdued marvel, stripping away his on-screen crutches—including his lively smile and playful sense of humor—to locate the fear, heartache, and confusion driving McBride’s journey to the stars. Renowned for his calm disposition even in the face of great peril, Pitt’s hero is often spied in empathetic close-ups, the better to allow the actor to convey the weight of the crises he’s been asked to remedy—ones that, in his mournful eyes and stout but heavy body language, take on personal, national, and spiritual dimensions. Far removed from so much of his prior output, it may be among his best work yet. — Nick Schager

12) The Curious Case of Benjamin Button (2008)

Few heartthrobs would agree to be digitally aged into shriveled old men, but Brad Pitt isn’t your average heartthrob. The premise of The Curious Case of Benjamin Button, cribbed from an F. Scott Fitzgerald short story, is simple: Benjamin Button ages in reverse, meaning that he is born old, and he dies young. Benjamin Button is a slow, leisurely film, a deeply human yet unsentimental story of the tortured relationship between love and time. As the title character, Pitt never gets lost in prosthetics or special effects—instead, he’s gentle and earnest, optimistic and romantic. The weight of the movie rests on Pitt’s digitally stooped shoulders. He knows it, and he never stumbles. —Adrienne Westenfeld

11) Tree of Life (2011)

Terrence Malick’s Tree of Life is a problematic fave, but one of my all-time faves nonetheless. In this too often-maligned movie, Malick’s subject is nothing less than cosmic time itself, seen through the microcosm of a suburban Texas family circa the 1950s. Pitt stars as Mr. O’Brien, a strict disciplinarian with impossible expectations who teaches his three sons to conflate love with fear. With his precise crew cut, pleated trousers, and mannered sternness, Pitt thoroughly exemplifies a particular mid-century ideal of paternal, all-American masculinity. Tree of Life is a masterpiece from a singular director, a sensual film with an assured, ambitious vision. Pitt is electrifying at the heart of it, embodying a towering, tormenting, demanding kind of love that believably organizes the internal weather of his three boys for decades to come. —Adrienne Westenfeld

10) Once Upon a Time in Hollywood (2019)

Pitt’s Cliff Booth is the down-on-his-luck stunt double for Leonardo DiCaprio’s struggling actor Rick Dalton in Quentin Tarantino’s ode to a radically shifting 1969 movie (and pop-culture) landscape. A dutiful right-hand man who’s both loyal and shrewd, Booth is a laid-back hunk who may or may not have also killed his wife. But, Pitt turns up the charm to almost absurdly captivating levels. Sunshiny gorgeous on the outside and yet possessed with a violent streak, he’s like the radiant Los Angeles he inhabits. From feeding his dog and fixing a rooftop antenna with his shirt off, to handling the Manson clan while zonked on hallucinogens, he delivers the finest performance in a film full of them, all understated cocksure swagger and easygoing wit.—Nick Schager

9) Fight Club (1999)

At risk of violating its first rule, Fight Club is the pinnacle of Pitt’s first leading-man decade, affording the star a heady, whiplash-inducing vehicle for his mixture of erudite wiseassery, male-model style and hypersexuality, and rugged masculine physicality (i.e. no one’s forgotten his twelve-pack). His Tyler Durden is the impossibly cool, good-looking id to Edward Norton’s wimpy ego, and their odyssey is fueled by Pit’s mega-watt charisma, which helps sell Durden’s non-conformist–and then outright anarchist–ethos. The film’s surprise twist may cause one to view Durden in a different light, but it does little to undercut Pitt’s force-of-personality portrait of unbridled macho rebelliousness. Whether duking it out with Norton in a parking lot, demonstrating the scarring power of lye, or assuming command of an army of disaffected white guys, he’s the irresistible black heart of a satire—about the fine lines between liberation and anarchy, freedom and fascism—whose timeliness hasn’t waned.—Nick Schager

8) Burn After Reading (2008)

Nothing could be further from Pitt’s Jesse James performance than his work in Joel and Ethan Coen’s Burn After Reading, a rollicking spy comedy laced with existential dread. With frosted tips and a perpetual dim-bulb grin on his face, Pitt is hilarious as Chad, a personal trainer who, along with coworker Linda (Frances McDormand), comes into possession of a top-secret CD coveted by various forces. His celebratory dance over their good fortune—while decked out in a tight-fitting, upturned-collar exercise shirt, lifting gloves, and headphones—remains a brief but unforgettable career highlight. And it’s emblematic of his entire turn, in which Chad’s adrenalized jock idiocy is amplified by his belief that he’s more than just a knucklehead. That’s never funnier than when he attempts to affect adult seriousness during a car rendezvous with John Malkovich’s government op, squinting heavily and speaking in a measured tone that can’t mask his juvenile cluelessness.—Nick Schager

7) Seven (1995)

Interview with a Vampire and Legends of the Fall cemented Pitt’s dreamboat credentials, but it wasn’t until 1995’s Seven that he truly connected with both male and female viewers. In the first of his three feature collaborations with director David Fincher, Pitt is a hotheaded detective paired with Morgan Freeman’s on-the-cusp-of-retirement vet, navigating a rainy city that’s as hellish as the Seven Deadly Sins-obsessed serial killer they’re hunting. With a buzzcut and matching goatee, Pitt’s Mills is a cocky man with a good heart and a lack of self-control, and that eventually makes him tailor-made to star in the film’s climactic tragedy. His desert-set freakout of horror, sorrow, and rage is some of the finest acting of his young career, and its resonance comes from his preceding work humanizing Mills in scenes opposite both Freeman and then-flame Gwyneth Paltrow as the cop’s wife. It’s a sterling performance of youthful intensity, sensitivity, and recklessness.—Nick Schager

6) Ocean’s Eleven (2001)

Ocean’s Eleven was one of the biggest box office hits off 2001, and it’s easy to see why: the endlessly re-watchable heist caper featured four of the era’s biggest movie stars, George Clooney, Matt Damon, Julia Roberts, and Brad Pitt. With Clooney in the role of the slick, seasoned con, and Damon as the new kid working his first major job, Pitt’s sidekick character Rusty Ryan can feel a little less defined. Still, Pitt imbues Rusty with some of the enticing menace he’d later bring to his role in Once Upon a Time in Hollywood. Like more than one Brad Pitt performance, he leans heavily here on his ability to be charming and handsome at the exact same time, but hey, if everyone could do it, he’d still be that guy from the Pringles commercial. —Gabrielle Bruney

5) A River Runs Through It (1992)

The two hours of this Depression-era period drama probably contain more fly fishing scenes than have been committed to celluloid in every other film in history. So no, the Robert Redford-directed movie is not the most action-packed project of Pitt’s career. Still, it’s one of the most moving, and in watching it now, it’s easy to see why Pitt remains one of Hollywood’s biggest names more than 25 years after its release. Based on the memoir of the same name by author Norman Maclean, the film documents the Montana coming-age-of the writer (Craig Sheffer) and his brother Paul, who’s played by Pitt. Sons of a reverend, Norman is the straight-laced, studious eldest while Pitt’s Paul is charming and tragic, a hard-gambling, hard-drinking rogue. They’re bonded by their love of fishing and the still-uncorrupted beauty of the American West. If you can get onboard with a movie that includes the capture of a large trout among its most pivotal scenes, the ending is sure to leave you blubbering. —Gabrielle Bruney

4) The Assassination of Jesse James by the Coward Robert Ford (2007)

There may be no 21st-century film more beautiful than Andrew Dominik’s The Assassination of Jesse James by the Coward Robert Ford (courtesy of Roger Deakins’ peerless cinematography), and no drama that more evocatively exploits Pitt’s marquee magnetism. Idolized by Casey Affleck’s obsessed acolyte Ford, Pitt’s James is something like a specter, materializing and vanishing without warning. Be it robbing a train or staring plaintively at the expansive plains, he’s the mythic celebrity at the heart of the American West, and Pitt embodies him as both a fanciful gunslinger fit for bedtime stories, and a volatile human being prone to vacillate between cheeriness and ruthlessness at a moment’s notice. On the one hand, he’s the prism through which the film investigates outlaw legends and, given the media’s fascination with James, our complicated relationship with icons. At the same time, though, Pitt—dreamy and intimidating in equal measure – shows us the less glamorous and easy-to-classify truth behind the tall tale. —Nick Schager

3) Inglourious Basterds (2009)

Though historical revisionism is sometimes questionable, it’s nice to imagine in an alternate universe in which Tennessee’s own Lieutenant Aldo Raine really did spend his time during WWII violently dispatching Nazis. Playing the pissed off, foul-mouthed lieutenant in Inglourious Basterds, Pitt’s Aldo Raine is one of Tarantino’s best characters. Then again, that makes sense considering that the director had Pitt in mind before he’d even finished writing the screenplay. The film was a massive success, both critically and commercially, landing a total of eight Academy Award nominations. Pitt was criminally left out of the conversation, but the legacy of his Southern accented, swastika-branding badass transcends award season. As such, Aldo might remain Pitt’s most famous performance of all time. —Justin Kirkland

2) 12 Monkeys (1995)

Pitt received his first Oscar nomination for Terry Gilliam’s 12 Monkeys, and it’s easy to see why—his Jeffrey Goines is a showboating role if there ever was one, all mannered ticks and flamboyant excessiveness. Inspired by Chris Marker’s seminal 1962 experimental short La Jetée, Gilliam’s haunting saga sends Bruce Willis’ time-traveler from a virus-decimated 2035 to 1996 to find the cause of Earth’s apocalyptic calamity, which he soon believes is related to Pitt’s wacko, whom he meets in a psychiatric hospital. With wildly darting eyes and arms and hands that can’t stop launching themselves in spastic directions, Pitt is like a cartoon character come to gonzo life. It’s an over-the-top tour-de-force, and though it sometimes feels a tad two-dimensional (thanks to the script’s need to mask Goines’ true nature), it makes up for its lack of depth with sheer, unbridled energy, which is wholly in tune with the film’s carnivalesque spirit. — Nick Schager

1) Moneyball (2011)

A movie about a bunch of old white dudes sitting around in conference rooms discussing baseball statistics doesn’t necessarily sound like a good time. It certainly doesn’t sound like the place for career high, Oscar caliber performances. Yet, thanks to a lighting fast screenplay from Aaron Sorkin and a truly emotive performance from Brad Pitt, Moneyball has a lasting legacy as much more than a great sports movie. Moneyball follows the true story of Billy Beane, the GM of the Oakland As, who used sabermetrics to build an astounding 2002 season team. It brought Pitt his third, and latest, Oscar nomination, and re-watching that final heartbreaking scene of Billy in tears, listening to his daughter’s song is enough evidence for why Pitt should have won the Oscar over Jean Dujardin in The Artist. Often times, Brad Pitt feels like he’s playing Brad Pitt, yet, in Moneyball, he truly disappears into the role of a father trying to figure his shit out. For all his iconic performances—the crazy ones, the sexy ones, the funny ones, the action-focused ones, it’s kind of nice to remember Pitt best as a dad trying to connect with his daughter. —Matt Miller

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