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Every Brad Pitt Movie Ranked Worst To Best

During a career that has now entered its fourth decade in film, Brad Pitt has proven time and again that he is more than just a pretty face. The 2020 Academy awards saw the prolific actor finally garner a win in the Best Actor category for Quentin Tarantino's "Once Upon A Time... In Hollywood." But the road to the industry's highest accolade has been paved with many obstacles, as he has had to overcome the beefcake image that made him a household name via shirtless scenes in "Thelma & Louise." Sure, having to overcome beauty is a challenge we'd all love to face — but over the years, Pitt's increased power led to grittier, more challenging roles, then finally Oscar glory. 

Pitt has been perfectly willing to mute his god-given physical attributes when the role calls for it: scruffy demeanor, lazy eyes, cockneyed accents and other tools have been employed in service of showing his range as a character actor. But undeniably, the man is a superstar of the highest caliber — perhaps one of the last true movie stars — and he has certainly amassed an incredible resume. 

Pitt has been featured in over 84 movies and TV shows (including a tongue-in-cheek blink-and-you'll-miss-it role in 2018's "Deadpool 2"). No Hollywood icon with such a long career can escape the occasional misfire, of course, but his successes certainly outweigh the failures — and even when he has failed, at least he has failed in interesting projects. So, which of Brad Pitt's films is your favorite? Here's a listing of his prominent roles, ranked from worst to best.

41. Cool World (1992)

The posters` for this Ralph Bakshi live-action/animation hybrid read "Holli Would if She Could" ... but audiences didn't. 

It's difficult even for an actor with as much natural talent as Brad Pitt to shine in such a muddled mess. "Cool World" creators tried to capitalize on the success of the live action/animation featured in "Who Framed Roger Rabbit?," but they don't seem to have learned any of the technical elements required to execute. 

As a result, "Cool World" is difficult to watch, and was such a notorious dud that it nearly killed Brad Pitt's career before it had begun. But hey, at least it resulted in one of the best soundtracks of the '90s.

40. Cutting Class (1989)

We're certain every actor has performances they would prefer be lost in time. Brad Pitt's role in "Cutting Class" is a rare moment of cringe from the otherwise magnificent thespian. His die hard fans would likely disagree — which is valid when you consider that even bad Brad Pitt is better than most. This late 80's high school flick tries to combine the slasher drama with a heaping scoop of comedy, but fails on both accounts. It is one of Pitt's lowest-rated films ever, and viewing it is an endurance test you should not take sober.

39. The Favor (1994)

Many have thought back on their high school days and pondered an alternate reality. "The Favor" tries to expand on those thoughts but fails to realize that infidelity is difficult to laugh at. Plugging Brad Pitt into a crowded cast still can't rescue poor scriptwriting. There isn't nearly enough of our boy Brad in "The Favor" anyways. Its mostly negative reviews and poor box office performance caused it to skate by most audiences unnoticed. An abysmal 27% critic's score on RottenTomatoes, and even lower audiences rating, tells the story: If you sit down to watch "The Favor," you're not doing yourself any.

38. By The Sea (2015)

Every now and then, one of these films come along that combine huge actors ... and somehow, little else. See "The Tourist," "Gangster Squad," "Showtime" ... better yet, don't.

Another head-scratching example — and the bottom of the Pitt film barrel — is this dreadful dud from 2015. "By The Sea” had him starring alongside then-wife Angelina Jolie in a drama set in 1960's France. The two play an American couple staying at a coastal hotel, as Pitt's character attempts to write a book and Jolie mopes about. Their marriage woes are meant to serve as the film's primary plot device, but somehow the film takes two of the most interesting people in the world and makes them extremely boring. This movie's only heartbreak is watching two superstars fail to sizzle.

37. Johnny Suede (1991)

Brad waded through mediocre territory before he truly blossomed into stardom; not necessarily by any fault of his own. Primo scripts tend to be reserved for the megastars, and in 1991 Pitt hadn't yet ascended to Hollywood glory. 

Tom DiCillo's "Johnny Suede" features Pitt as the titular character, sporting the most exaggerated pompadour you have ever laid eyes. Johnny has aspirations of being a rock 'n' roll icon and believes it achievable when a pair of suede shoes descend from the heavens. This indie film was constructed on a $500k budget and didn't even manage to cross the $100k mark on its release. A few years later, DiCillo would break through with "Living in Oblivion," a comedy about indie filmmaking and an egotistical star, who some believe was based on the director's experiences on this film with Pitt.

36. The Counselor (2013)

On paper, "The Counselor" has all the makings of a fantastic crime drama. Behind the camera is legendary director Ridley Scott; in front is a loaded cast that includes Michael Fassbender, Penelope Cruz, Cameron Diaz, Javier Bardem, and Brad Pitt. Despite all the elements of success, "The Counselor" winds up being a snooze fest. All the characters' ramblings will likely cause you to zone out while staring at the television. 

This does, however, create room for Pitt's character and one of the more memorable on-screen deaths of the last few years. Pitt's demise via bolito might possibly scar you for life, but the expertly-orchestrated scene is well worth watching.

35. Kalifornia (1993)

"Kalifornia" is perhaps best remembered as a snapshot of a young Brad Pitt finding his way in the acting world. 

Once again starring opposite a real-life paramour (he was dating Juliette Lewis at the time), the film tells the story of a journalist (David Duchovny) and his girlfriend (Michelle Forbes) as they clash with a deranged killer (Pitt) and his girlfriend (Lewis). The deranged flick has its moments, Roger Ebert was a big fan of the performances by Pitt and Lewis, and it established rookie director Dominic Sena ("Gone in Sixty Seconds") as a talent to watch. But if your morbid curiosity has you planning to make "Kalifornia" part of your evening viewing, keep in mind there are more than two dozen better Brad Pitt movies listed below. 

34. War Machine (2017)

This is the first "scenery-chewing Pitt" performance on the list, as he was cast against type — and is clearly relishing it. 

In this high-budget Netflix film, Pitt is boisterous four-star general Glenn McMahon, who inherits control of the troops in Afghanistan — and a meandering plot that has no idea where it wants to go. Pitt's portrayal of the general often feels like the only thing in the film that is trying hard, and its aimlessness is fascinating because it's based on a true story, yet "War Machine" can't seem to remember why it wants to tell this particular story so bad. If you're looking for Brad Pitt's best attempt at a "Dr. Strangelove"-type film, it's worth a curiosity viewing. But war is hell — and so is watching "War Machine."

33. The Mexican (2001)

Speaking of films that promised big stars but ultimately left fans disappointed, this breezy Gore Verbinski action comedy paired Pitt and Julia Roberts — possibly the two biggest movie stars in the world at the time — but left them wanting more.

Like "Kalifornia," this film is remembered as lesser Pitt but has plenty of good things going for it. The two leads are clearly enjoying each other, a pre-"Sopranos" James Gandolfini shines as a gay hitman, and there are solid supporting turns from JK Simmons, Bob Balaban ... all punctuated by a Harry Lime-like cameo from the immortal Gene Hackman.

All of the above are jockeying for position ins search of a near-mythical antique pistol, with Pitt playing a goofy errand runner for the mob. This is the list's first sighting of "quirky Pitt," as his character takes delight in El Caminos, stumbles around Mexico and nearly gets himself killed a half dozen times; his character feels like a distant cousin to the Pitt in "Burn Before Reading." But ultimately, although "The Mexican" tries its darnedest to be quirky good, it too often winds up quirky boring.

32. The Devil's Own (1997)

Brad Pitt and Harrison Ford! What could go wrong? Try ... everything.

"The Devil's Own" is remembered today (if at all) as a mediocre crime drama from 90's. Its primary redeeming quality is undoubtedly the star power of its lead actors, but the simplistic plot concerning an officer (Ford) and his sketchy house tenant (Pitt), barely gets this film out of the gate.

We all know the "Devil" is in the details, and in this case the revelation that Pitt's character is an IRA member on a stateside trip to procure illegal guns for the cause feels more contrived than convincing. A rare misfire from Alan J. Pakula (in what would be his final film), "The Devil's Own" attempts to tell a story of moral conflict, but succeeds only in showing us that Brad Pitt sure sounds swell with an Irish accent.

31. Killing Them Softly (2012)

In retrospect, "Killing Them Softly" might be one of the most fascinating films Brad Pitt has ever been a part of. Made, advertised and sold as a badass Brad Pitt action film, when audiences saw it on opening weekend, they were expecting precisely that. What they got instead was a dark mediation on the shortcomings of capitalism and American decline, delivered in a wannabe Coen Bros/Tarantino style that came up short. It received a rare "F" from audiences on CinemaScore who had seen the film — as of 2021, only one of 22 movies to ever rank so low — and clearly they weren't happy about being sold a false bill of goods by the Weinstein Company. 

Nonetheless, any Brad Pitt movie possesses an inherent enjoyability merely because Brad Pitt is in it. This time around, he plays a hitman brought in by mafiosos to take care of two junkies who ripped off a local poker game. "Killing Them Softly" promised a lot of things (including a fun time) but just didn't deliver. 

30. Ocean's Twelve (2004)

Typically, sequels aren't known for achieving the grandeur of their predecessor. "Ocean's Twelve" further bolsters that theory. The cast of the original is largely intact, but a lackluster story plot never fully delivers. That being said, it is still entertaining to watch the chemistry between all these Hollywood A-listers. Brad Pitt returns as Rusty Ryan and is dapper as always — and continues to munch on any snacks he can get his hands on. You'll have fun watching Pitt hang out with everybody, but the finale results in a disappointing "twist".

29. Ad Astra (2019)

Released in 2019, "Ad Astra" was barely able to recoup its massive $90 million budget (having to resort to worldwide numbers to achieve profit). The presentation proved much too slow for the general public. 

In the film, Pitt stars as astronaut Roy McBride, sent on a mission to reconvene with a ship marooned near Neptune. The craft possibly contains his father, who went radio silent 16 years earlier. The film goes to great lengths to depict how much difficulty McBride goes through, how many times he risks his life, to find his father — then become inadvertently hilarious in its last reel as he finally reaches the outermost of outer space to discover the old man (played by Tommy Lee Jones) seems interested in little more than berating his son and making him miserable. 

28. The Tree of Life (2011)

This philosophical, life-spanning journey from Terrence Malick dared to explore the big questions. In some ways, it proved too cerebral for mass appeal — even if it is cited by some as one of the great filmic achievements of the last several decades; in other ways, it's a Terrence Malick movie, so it wasn't designed to inspire a ride at Universal Hollywood.

The movie's gorgeous visuals and daring narrative (Malick hallmarks) carry the film, along with stellar performances from Sean Penn, Jessica Chastain, and Pitt. "Tree of Life" is a dive into the mystery of existence, centered around a family living in Waco, Texas in the '60s. Pitt's role is a rare instance in which he isn't meant to be likable. His character eventually seeks redemption, but achieving it is a slow crawl not intended for the faint of heart.

27. Seven Years In Tibet (1997)

This epic was a major turning point in Pitt's career, as he was beginning to take movies that meant something to him rather than mere paychecks; whether the film works, however, is still up for debate. 

Some posit a misplacement of the character narrative, stating that its supplemental stars (BD Wong & Mako) had more intriguing stories to tell. Brad Pitt aficionados would claim the narrative is placed exactly where it should be. 

"Seven Years in Tibet" is a personal journey you need to take in order to decide for yourself. It centers on the story of an Austrian mountaineer, Heinrich Harrer (Pitt), who is trapped in the foreign land of Tibet during the tumultuous developments of World War II. The resulting friendship with the Dalai Lama and his own spiritual enlightenment are sourced from Harrer's 1952 memoir. Pitt can appear out of place amongst the film's backdrop at times, but at other times he looks perfect.

26. Mr. & Mrs. Smith (2005)

Somehow, this film — best remembered as the set where Brangelina was born — became a huge blockbuster success. But at the time, it was notorious for its  perceived troubles, and despite the best intentions of talented director Doug Liman, if you revisit the final result today you'll discover something of a mess. 

The action riddled rom-com has one thing going for it: the on-screen chemistry of two superstars whose flirtations brought much life to a dim-witted script. There are some fun action sequences, fueled by witty banter between the titular assassin couple, assigned by their adversarial agencies to eradicate each other. Brad and Angelina are able to reignite a spark in their waning relationship when their respective secrets are unveiled — and the result was nearly $500 million at the worldwide box office, even if the film barely sits at 60% on RottenTomatoes.

25. Ocean's Thirteen (2007)

Despite the mediocre reviews for "Ocean's Twelve," it still performed exceptionally well at the box office (it raked in a cool $362 million worldwide). Its success allowed for a third addition to the Ocean's catalogue in "Ocean's Thirteen." 

Most of the original cast reconvened, along with director Steven Soderbergh, who added Al Pacino to the ensemble. Writers appeared to have learned from their mistakes on "Twelve," creating an elaborate heist involving Pitt and Clooney dismantling an entire casino kingpin's (Pacino) legacy. It's unlikely we will again see an ensemble of this magnitude, which makes all the "Ocean's" films worth having in your media library. With this final installment, this collaboration went out in style.

24. Allied (2016)

Director Robert Zemeckis has spent over three decades as a Hollywood golden child, delivering hits like "Back To The Future", "Forrest Gump", and "Cast Away." Imagine the excitement when he got behind the camera for a World War II epic, aiming it directly at Marion Cotillard and Brad Pitt. 

The resulting film is "Allied," and it is a historical romance thriller that wound up being carried by the acting duo. The movie's era feels less like a page from history and more like a fairy tale with lots of pretty, soft lights. It's a rare miss for Zemeckis, but Pitt and Cotillard make it worth the watch. Audiences and critics agreed on being largely unable to define their feelings about "Allied." We'll be bold and claim ... it's fine.

23. Spy Game (2001)

Slapping together two generations of blonde-haired sex appeal is a recipe for success, one that director Tony Scott capitalized on with "Spy Game". Simply put, it is good, old-fashioned Hollywood cinema entertainment. It doesn't try to be anything grandiose, but still captures an intriguing story of multinational government espionage. 

Brad Pitt plays CIA operative Tom Bishop, who is captured in China amidst crucial trade talks with the United States. His actions are unsanctioned by the government and jeopardize the unity of these two superpowers. Bishop's mentor, Nathan Muir (Robert Redford), is brought in to help with handling the situation. The ensuing "Spy Game" is a diplomatic nightmare. One that is told with flashbacks to Muir and Bishop's days training together. "Spy Game" was barely able to recover its massive budget, but time has treated it well.

22. Troy (2004)

The epic tale of Homer was brought to the screen in 2004 in this Wolfgang Petersen swords-and-sandals epic, with Pitt cast as the legendary Achilles. The actor acknowledges it was a misfire — but a crucial one that taught him some essential truths about how to guide his career.

"It was really a turn on 'Troy.' I was disappointed in it. When you're trying to figure things out in your career, you get a lot of advice. People are telling you that you should be doing this, and other people are saying you should be doing that," he told the New York Times Magazine in 2019. "[The failure of 'Troy'] really made me think, I'm following my gut from here on out. I had to do Troy because — I guess I can say all this now — I pulled out of another movie and then had to do something for the studio. So I was put in 'Troy.' It wasn't painful, but I realized that the way that movie was being told was not how I wanted it to be. I made my own mistakes in it ... somewhere in it, 'Troy' became a commercial kind of thing. Every shot was like, Here's the hero! There was no mystery. So about that time I made a decision that I was only going to invest in quality stories, for lack of a better term. It was a distinct shift that led to the next decade of films."

What remains is Pitt playing the mythic hero in a somewhat-grounded representation of who the warrior may have been in real life. The flick promises a grandiose depiction but doesn't quite level up to its grandiose intentions. Regardless, it's still worth a viewing, if only to see Pitt shine as a fighter with nigh unstoppable agility. Were it not for Achilles' incredible physique and intoxicating arrogance, it's unlikely "Troy" would have achieved even its modest box office pull.

21. World War Z (2013)

Pitt hopped on the zombie bandwagon with this Marc Forster flick, another one that was known for production difficulties before its release, but turned out to be far better — and more profitable — than some expected. 

In the tradition of "28 Days Later," "World War Z" subscribed to the running zombies school of depiction, becoming a cornerstone of post-Romero living dead films. These speedy carnivores possess the ability to move in terrifying waves, sweeping across obstacles, climbing any defensive barricades and even forming rudimentary ladders atop each other

Pitt plays Gerry Lane, a former UN field agent who returns to active duty in order to discover the source behind a global zombie pandemic. Lane is forced to leave his family aboard a Navy vessel to fly into enemy territory to find the virus' source in order for a vaccine to be created. Nearly a decade later, this is perhaps the one Pitt film most frequently rumored to have a sequel in some stage of development ... but as much as it felt like a tale at the end with more to come, at the moment the franchise seems unlikely to rise again.

20. Meet Joe Black (1998)

In the midst of his late 90's mega-stardom, Brad Pitt nearly killed his entire career.

Stepping into the role of Death in "Meet Joe Black," Pitt and Anthony Hopkins teamed up for a film by "Midnight Run" mastermind Martin Brest that — coupled with Brest's infamous Ben Affleck bomb "Gigli" — drove the filmmaker out of Hollywood.

While the title of the role suggests thriller, this is a romantic tale that is a test of endurance. The film's three-hour runtime makes a bottle of wine a requirement for viewing it in its entirety. We'd say it's worth the journey, even if the film's box-office would disagree. 

Pitt's turn as Joe Black is one of his more reserved roles, but it fits with the story being told. Editors could have chopped off about an hour of staring and smoldering, but otherwise "Meet Joe Black" is mandatory viewing for any Brad Pitt viewing marathon.

19. Burn After Reading (2008)

Perhaps the flat-out goofiest Pitt has ever been on-screen, he is clearly having a lot of fun in this underrated Coen Brothers classic — and we all have the .gifs to prove it.

Cast as a dim-witted personal trainer who works at a gym alongside Frances McDormand, the film takes off when the unlikely duo discover a CD (compact disc, for any of you kiddos scratching your heads) in the locker room that they believe to contain sensitive government files. Naturally, they attempt to blackmail its owner to raise money for cosmetic surgery, and all hell breaks loose. Various plots intertwine to create some zany outcomes, orchestrated marvelously with Coen deftness. "Burn Before Reading" brought audiences a very fun version of Brad Pitt, one we still don't get to see nearly enough.

18. A River Runs Through It (1992)

This Robert Redford directed tale was Brad Pitt's first taste of genuine critical appeal. "A River Runs Through It" was nominated for three Academy Awards and took home a win for Best Cinematography. 

Pitt plays Paul Maclean, one of two brothers who bond over fishing excursions at a river in Montana. The movie was a modest box office success, but is known more for the directing prestige it bestowed on Redford and the stepping stone it offered for Brad Pitt's career. You wouldn't expect a movie about the bond of fly-fishing to be particularly captivating, but the combined might of Hollywood legends made "A River Runs Through It" a crucial moment in Brad Pitt's career. Not to mention, Tom Skerritt's representation of the brothers' father (Reverend Maclean) is near perfection.

17. Babel (2006)

Helmed by Alejandro Iñarritu ("The Revenant"), "Babel" has an epic plot that spans four continents and features numerous characters in their own individual storylines. The result was a now-classic drama that earned seven Oscar nominations.

Pitt shines as Richard Jones, who alongside his wife Susan (Cate Blanchett) is on vacation in Morocco when she is randomly shot on a tour bus by some young goat herders recklessly toying with a rifle. The two Western tourists are abandoned by their group as they wait for help, leaving an anguished Pitt to helplessly wait in the heat for an ambulance that never arrives.

While the scattered plot of "Babel" can make for a difficult watch, it is well worth the effort for both the beautiful cinematography and skillful acting of stars like Pitt, Blanchett, Adriana Baraza and Rinko Kikuchi.

16. Legends of The Fall (1994)

This is a strange entry in the filmography of Pitt, because on the one hand the movie was seen by most as underwhelming (it currently sits at 58% on Rotten Tomatoes), but on the other, it was one of the first films where Pitt was marketed as a true star — and all those ads featuring his rugged, blonde beauty at its best made arguably a bigger impression than the film itself.

Pitt was at risk of being typecast purely as a pretty boy in this "Legends of The Fall" period, but nonetheless, his portrayal of a young man dripping with melancholic, sensual energy helped carry the film to a solid box office. Set in the early 20th century, "Legends" is directed by Edward Zwick and put Pitt alongside Anthony Hopkins, Aidan Quinn and Julia Ormond, telling the tale of siblings who suffer the loss of their youngest brother (Henry Thomas) while fighting against the Germans. The subsequent fallout amongst the family is both tumultuous and heartbreaking. 

These days, critics may disagree — but anybody who was around in the '90s will cite "Legends" as essential Brad Pitt cinema viewing.

15. Sleepers (1996)

A powerful, star-studded, well-intentioned film that just can't seem to get out of its own way, "Sleepers" may rank among the most intense crime dramas of its period.

Pitt plays a New York attorney alongside Robert De Niro, Dustin Hoffman, Billy Crudup, Jason Patric, Minnie Driver, Brad Renfro and Kevin Bacon (an essential film for anyone who ever hopes to excel at the "Six Degrees" game), spanning 13 years and telling the heartbreaking tale of four childhood friends' physical and sexual abuse at the hands of sadistic guards at Wilkinson Home for Boys in Upstate New York. 

Directed by Barry Levinson and based on a true story, "Sleepers" follows the friends as they reconvene years later after two of the boys spot the head guard responsible for their abuse at a pub and murder him.

14. The Assassination of Jesse James by The Coward Robert Ford (2007)

Aka the longest-titled film of the last twenty years, this 2007 Western centers on the fascinating life of outlaw Jesse James (Brad Pitt) — and the man who would bring him down.

Robert "Bob" Ford (Casey Affleck) has an initial desire to join Jesse James' gang, alongside his brother Charley (Sam Rockwell). As he gets closer, however, his idolization of James turns into a toxic resentment. The title can likely give you major hints as to the titular character's inevitable demise, but the intricate plot details that lead to its fulfillment are worth the journey. Written and directed by Andrew Dominik, the end result earned Affleck an Oscar nomination, and remains a fascinating American tale about the pursuit of glory and its unfortunate side-effects.

13. Interview with the Vampire (1994)

An absolute sensation in the build-up to its release, this big screen adaptation of Anne Rice lives on in cinematic history as an incredibly difficult shoot turned into a flick every bit as haunting and memorable.

It also likely gave birth to the modern-day vampire angst of everything from "Vampire Diaries" to the "Twilight" films, thanks in large part to Pitt's performance as Louis de Pointe du Lac alongside Tom Cruise's immortal Lestat de Lioncourt. "Interview" is told in modern times by Pitt's character to a reporter in San Francisco (played by Christian Slater, who took over at the 11th hour when originally-cast River Phoenix died). 

The woes of Pitt's character begin in 1791, when he first meets Lestat and is infected with the curse of vampirism. Along their journey, the duo turn a young girl (played by Kirsten Dunst) into their kind, and she comes to resent them for rendering her unable to ever physically mature as a woman. In service to this centuries-spanning tale, Pitt showed a new side of himself while furthering an ascension to superstardom.

12. Fury (2014)

In David Ayers' brutal "Fury," Pitt shines as Sergeant Don "Wardaddy" Collier. Coupled with "Inglorious Basterds" (which would make a heckuva double feature), the military men might just represent two of his greatest performances.

The film takes place in 1945, during the Western Allied invasion of Germany. Fueled by a hearty helping of wartime angst, the film vividly captures the day-to-day of Collier's platoon, which sports a Sherman tank armed with a high-velocity 76mm gun (nicknamed Fury). The group of soldiers (among them, standout performances from Jon Bernthal and Shia LaBeouf) are burdened with the inexperience of a private named Norman Ellison (Logan Lerman) whose only experience prior to this assignment involved paperwork. When the troop's tank is immobilized by a landmine, they are forced to make one final stand against an overwhelming number of German soldiers.

11. 12 Years A Slave (2013)

Although Pitt's on-camera role is fairly minor in this vital, Oscar-winning film, his behind-the-scenes work was essential in getting it made.

The film, which tells the horrific story of Solomon Northup (Chiwetel Ejiofor) and is based on the real-life 1853-published memoir by the enslaved man, is as intense a viewing experience as they come. Northup, a New York musician hired to travel to Washington D.C. for paid work, ends up being drugged and sold into slavery — leading to a lengthy, torturous journey on the road to once again become a free man. 

While Pitt's work is a side character in "Slave" (he's a Canadian worker on one of the plantations who delivers a letter home for Northup), the film's pedigree (9 Oscar nominations and 3 wins, including Best Picture) warrants inclusion on any list. Essential viewing for cinephiles and Brad Pitt fans alike, the film secondarily went a long way towards reminding Hollywood that Pitt was not only an in-demand actor, but also a powerful producer with both good intentions and excellent instincts.

10. The Curious Case of Benjamin Button (2008)

In one of his most ethereal roles, Pitt teamed up for a third time with Fincher for the timeless tale of a man born with an unexplainable condition that causes him to age in reverse. The movie showcased state-of-the-art CGI work that left audiences in awe, wiping away tears, and ultimately watching the film pick up 3 Oscars at that year's Academy Awards. 

Benjamin emerges from the womb as an elderly infant, suffering a childhood wrought with afflictions typically reserved for those with an AARP card. His journey takes him around the world, where he meets a variety of colorful characters all on their own tormented life journeys. The miracles of CGI bless the epic film with a unique range of Brad Pitts, spanning from wrinkled child to smooth-skinned teenager, and as you can imagine, it gives an actor a diverse palette which Pitt put to good use.

9. The Big Short (2015)

The 2007-2008 US housing crisis was a devastating ordeal for countless Americans, made worse by the government's insistence that the "Too Big to Fail" financial institutions that drove the disaster deserved a do-over. Many were left asking: what the hell happened? 

The first of several star-studded "serious" films from "Talladega Nights" director Adam McKay (his latest being "Don't Look Up"), this flick brought together Christian Bale, Steve Carell, Ryan Gosling, Pitt and Margot Robie (in a bubble bath) to explain the madness. 

Pitt plays retired securities trader Ben Rickert, a mentor, of sorts, who catches wind of the inevitable burst of the housing bubble. Rickert, along with all the other players portrayed, try their best to alert the powers-that-be to the incoming crisis but their warnings fall on deaf ears. Rather than standing on the sidelines to watch the country crash and burn, they place massive stakes on shorting the housing market.

8. Moneyball (2011)

Whether your knowledge of baseball is limited or expansive, Bennett Miller's Oscar-winning "Moneyball" deftly navigated the game in telling a tale that explored the glories of thinking outside-the-box, utilizing data and an open mind to turn the tables on any powerful adversary.

Pitt tells the real life story of Oakland Athletics' general manager Billy Beane, who alongside Peter Brand (Jonah Hill), found themselves tasked with constructing a winning Major League Baseball team despite having a payroll that was a fraction of what big market teams could pay. Recruiting never-was players and other diamonds in the rough, they utilized cutting-edge stats to uncover value where others saw one, constructing an A's roster that consistently made it to the postseason.

Sure, the movie has its issues (in real life, the 2002 A's were anchored by superstars Barry Zito, Mark Mulder, Tim Hudson and MVP Miguel Tejada, who are barely mentioned if at all), but Pitt's performance goes a long way towards making an otherwise mundane subject matter captivating.

7. Ocean's Eleven (2001)

Combining the cumulative star power of a Hollywood era is a feat few directors have been blessed with. But director Steven Soderbergh was in the right place at the right time (with the right friends) when it came time to remake the Rat Pack classic "Ocean's Eleven." 

Perhaps the definitive heist film of its generation, Soderbergh's "Eleven" placed Pitt among a star-packed ensemble, yet he shined as brightly as anyone. Pitt's Rusty Ryan, a professional thief working alongside George Clooney's mastermind Danny Ocean, possesses a calm demeanor that helps the feisty thieves come together to pull off a casino heist for the ages. Pitt's input into the character also resulted in a running joke, as he wanted to be eating or drinking something in every scene. From nachos to shrimp, in more ways than one it was a delicious performance.

6. 12 Monkeys (1995)

This Terry Gilliam-directed mind-bender was one of the first films to show Pitt's ability to truly lose himself in a character, sacrificing his good looks for a good performance. Starring Bruce Willis as a time traveler sent back to gather information about a viral outbreak that decimates the human population, "Monkeys" details the dangers of time travel by putting his character in a mental institution where he meets Pitt, playing the son of a virologist who is adamantly anti-corporation and pro-environment. Make no mistake: Pitt never would have landed "Fight Club" if he hadn't first shown what he could do in "12 Monkeys." Even if, in his mind, the performance was something of a failure.

"I nailed the first half of '12 Monkeys; I got the second half all wrong," he told the New York Times Magazine in 2019. "That performance bothered me because there was a trap in the writing. It's not the writing's fault, but it was something that I couldn't figure out. I knew in the second half of the film I was playing the gimmick of what was real in the first half — until the last scene — and it bugged the [expletive] out of me."

The wacky, cock-eyed Goines is a vibrant jester amongst the film's bleak landscape. Gilliam was nervous about Pitt's ability to pull off the manic, rapid-fire speech patterns required to properly represent Goines, so he wound up depriving the actor of his cigarettes. Despite Pitt's bittersweet remembrances, his scene-stealing portrayal of a zany activist dead set on unleashing mayhem on the corporate landscape was a crucial role in his development as an actor.

5. Snatch (2000)

Brad Pitt has the capability to entrance an audience, even when they can hardly understand a word he is saying. 

In Guy Ritchie's 2000 cult classic "Snatch," Pitt plays a member of a roaming band of gypsies named Mickey O'Neil, who also happens to be a bare-knuckle boxing champion. His cockneyed accent is so amusing, it hardly matters that you have to press "subtitles on" to make sure you don't miss any key plot points. 

O'Neil's nomadic, thievish nature seems like he may have embraced such unintelligibility to help confuse those around him — whatever the motivation, it sure is fun to listen to. Pitt receives less screen time than his co-stars in "Snatch," yet still steals the show, as the most memorable aspects of the film are his off-the-wall dialogue and scrappy demeanor.

4. Inglourious Basterds (2009)

As if setting a theater filled with Nazis ablaze isn't enough, Quentin Tarantino's "Inglourious Basterds" also gave the national treasure known as Brad Pitt one of his greatest roles. 

Cast as Lieutenant Aldo Raine, a United States commander during World War II, Pitt's character vows to fight fire with fire by recruiting a team of unrelenting, scalp-collecting soldiers. If the Nazis they face are determined to inflict cruelty upon the Jewish population, Raine sees fit to match it with his own brand of justice, invoking fear in those feared by millions.

Pitt's charming southern accent and period-appropriate mustache bury him deep in character, to a point audiences rarely see from the star. It all helps bring a smile as he marches his troops into enemy territory, retaliating against Germany with war crimes of their own.

3. Se7en (1995)

David Fincher's darker-than-dark crime classic not only made "What's in the box?!" a classic movie quote, but captured the Pitt/Fincher grit that fueled several of his best mid-'90s/mid-'00s efforts. 

With Morgan Freeman by his side, Pitt perfectly embodied the idealistic younger cop blind-sided by the sadistic schemes of serial killer John Doe (Kevin Spacey, in a role that was largely kept secretive from the public to hide his identity). Hollywood has a proclivity for happy endings, Fincher has a famous hatred of them, and the final act of "Se7en" will have you regretting any assumptions. 

Pitt's portrayal of Detective Mills is among his finest, the finale is absolutely heartbreaking — and he sells it perfectly. "Se7en" leaves you questioning your virtues and fearing the wrath buried deep inside even the purest of souls — and marveling at the brilliance of its design.

2. Once Upon A Time... In Hollywood (2019)

Pitt's second collaboration with Quentin Tarantino (third if you count "True Romance," which Tarantino wrote and Pitt shines in a handful of brief scenes) proves once again that the blonde-haired leading man operates at his best when directors dial back on his suave beauty and allow him to get his hands dirty. 

Cliff Booth serves as a hallmark of later-career Pitt. Sporting the swagger of a man who has evaded the sands of time, the story of a stunt man playing second fiddle to a superstar in the '60s simply wouldn't swing if not for Pitt — even if, as Bruce Lee says "You're kinda pretty for a stuntman." His actions dance the line of rational and homicidal — after all, how many films can you think of where a beloved character may have murdered his spouse in cold blood, but we still love him? — filling the viewer with so much joy that you can't help but cheer at the cathartic bloodshed.

1. Fight Club (1999)

Behold the glory of The Alpha Brad! While it may seem foolhardy to claim a peak in Pitt's career, his turn as Tyler Durden in "Fight Club" is the pinnacle of acting stardom, and an iconic film of the highest order. In fact, we're hesitant to talk about "Fight Club" because ... well, you know. And the fact that you get that joke shows just how iconic the film still is after all these years.

Sporting a physique that deserves enshrinement among the pantheon of marble statues glorifying the human form, he embodied the psychosis of a man grappling with the mundanity of societal expectations. Tyler's smirky cynicism is so contagious, you will find yourself wishing Norton's narrator would fall prey to the whims of his sociopathic alter ego. Tyler's long-winded diatribes are spellbinding, and his frustrations with the world are set behind a roguish charm that helps you laugh at the many punches life throws at you. 

This, the definitive Pitt role, is a career-defining punch to the ear in an already remarkable career.