Immortality: Brad Pitt's 25 best performances

For Pitt, who made his bones as an onscreen sex symbol, diving into Steven Soderbergh's remake of “Ocean’s Eleven” was a prime opportunity to allow him to loosen up and play a role with practically no pretense, as here he is not the center of attention but part of a larger fabric that puts him in a comfortable space with the audience. Soderbergh allows Pitt the scenes to feed off his inherent coolness as opposed to making his coolness the point, and that reflected well in the final product, and his two follow-up films in the "Oceans" series.

After his debut in 1991's "Thelma & Louise," Pitt swings for the fences as an outlaw of a much darker stripe in Dominic Sena's low-budget thriller "Kalifornia." Pitt is both sinister an electric as Early Grayce, an ex-con travelling with his yokel girlfriend (Juliette Lewis) after figuring that it was easier just to kill those who got in his way as opposed to actually following the rules of his parole. Pitt dives deeply and successfully into the role of bad guy, something we wouldn't see from him again until the No. 1 film on our list.

As Maj. Roy McBride in James Gray’s space saga “Ad Astra,” Pitt stretches himself further than normal, imbuing his character with a sense of duty that masks his massive daddy issues. While this might sound overly melodramatic, Pitt delivers with the right amount of gravitas and grace that allows viewers to truly enjoy a story that feels like a mix between "Interstellar" and "Apocalypse Now."

A deep contrast from his previous WWII turn in Quentin Tarantino's "Inglourious Basterds," Pitt steps into the role of battle-hardened Army sergeant Don "Wardaddy" Collier, bearing scars both on the inside and out as he leads his five-man Sherman tank crew in the waning days of the war. Pitt straddles the line between noble and brutal, dispensing bullets and wisdom with an equal aplomb as the odds stack up against the small crew, with survival growing bleaker by the moment.

Even in a middling sword and sandals epic, Pitt stands above the rest of his cast as the legendary warrior Achilles. "Troy" chooses to eschew the mythology and focus more on a grounded story of Trojan War. As Achilles, Pitt balances earned arrogance with a sense of tragic perception as his reluctance to go to war with Troy is beset by his thirst for battle.

A few comparisons are made between this film and the later "Legends of the Fall," particularly when it comes to Pitt, but director Robert Redford leans into Pitt's roguish charm, helping him create a cocky, dashing and tragic character in Paul Maclean, a fun-loving and wild child who still cherishes his time fishing with his brother (Craig Sheffer) and father (Tom Skerritt).

As hitman Jackie Cogan, Pitt brings a stoic cynicism to this neo-noir tale featuring a smattering of guns, gangsters and junkies, where he's tasked with cleaning up all the necessary and unnecessary messes of those who thought they were smarter than the games they were playing in the streets. As philosophical as it is cynical, Pitt wades through the film with every bit of his magnetic charm. While the film itself may not be the greatest, his performance floats the film more than enough to earn a view.

Starring alongside Cate Blanchett for the first time after (the second being "The Curious Case of Benjamin Button"), Pitt plays the role of a grief-stricken father and husband on vacation, who finds himself struggling to find peace after a terrible tragedy. Pitt is at his near-best as his character grapples with the pain of current and past problems threatening to swallow him whole as he reaches a breaking point.

While so much of director Marc Forester's adaptation of Max Brooks' acclaimed novel was as much a disaster behind the scenes as the disaster depicted on screen, the sole bright spot was Pitt's leading performance as former United Nations employee Gerry Lane, tasked with finding out how a zombie outbreak happened and what could possibly stop it. Pitt takes his role ultra seriously while never being ponderous, delivering a turn that manages to keep the film grounded even as all hell is breaking loose around him.

As supporting roles go, Pitt found himself a gem in Adam McKay’s eclectic and humorously accessible depiction of the 2007 housing market collapse. Alongside stellar performances from leads Christian Bale and Steve Carell, Pitt manages to steal the show in his scenes as adviser Ben Rickert, a conscience of sorts to the other characters, giving him the chance to melt into a role that allows him to place another unlikely feather in his character actor cap.

In 2011, Pitt got his chance to work alongside enigmatic director Terrence Malick in his haunting meditation on family, memory and the origin of life. As O'Brien, Pitt is working overtime delivering some of the better, if not most subtle, work of his career as a typical family man in midcentury Texas. Pitt balances both an aggressive and tender side as he dotes over and also faces off against his children, and it's this sort of ambiguous approach that at times makes his performance uncomfortable but ultimately satisfying. 

As vampire Louis de Pointe du Lac, Pitt brings a world-weariness that pits him well alongside the surprisingly deft performance of Tom Cruise as Lestat in this adaptation of Anne Rice's modern classic. While his role is supporting, Pitt aptly serves as the film's connective tissue, and the audience learns more about the pain and pleasures of a vampire's long life through Louis' eyes than any other character, including Lestat himself. 

Pitt smolders with a tortured vague mysterious vibe in Edward Zwick's historical epic, starring as the tempestuous Tristan Ludlow, an early 20th century veteran who finds a different war on the homefront as he struggles with his family and his own heart as the things he wants most are the things she can never truly have. Pitt brings more than a fair share of dashing charm here, along with a matching amount of darkness for this complex and conflicted character.

Pitt's third outing with director David Fincher is both his most peculiar and poignant. Starring in this melancholy tale of a man who ages backward, Pitt tackles the role with a sense of wonder, tugging on the heartstrings of viewers as he portrays Button as affable and engaging, experiencing the world in a way few "normal" people would ever know. A good part of "Button" deals with the titular character's love affair with a woman (Cate Blanchett) who is as fascinated by Button as she is in love, despite the sadness to come, and it's here where Pitt shows both magnanimity and tenderness as his love for her matches that of the world around him.

"Thelma & Louise" features Pitt in a star-making turn as J.D., a hunky drifter with a penchant for armed robbery. Leaning heavily into his dreamy looks, Pitt is in full heart-throb mode here, but not so much that you don't notice a star in the making. His demeanor has an "aw, shucks" feel, by design, though it thinly veils a much more calculating individual. Here, Pitt has easygoing charm to spare, and he remains an enjoyable glimpse at a rising star.

Continuing his immersion into character actor status, Pitt stretches his legs in this Coen Brothers satire as Chad Feldheimer, the sunny and harmlessly naive co-worker of Frances McDormand’s Linda Litzke, as the pair come up with a hairbrained blackmail plot involving the CIA and a few interesting agents. While his scenes are few, Pitt creates a memorable character who carries the film to a surprising twist.  

In a casting move both ironic and inspired, director Guy Ritchie gives Pitt possibly his most complex and hilarious role as a gypsy boxer with a thick Irish accent who literally plays by his own rules in "Snatch." As O'Neil, Pitt delivers a showstopping performance that furthers his reach as a character actor clearly having fun with a role few would expect him to pull off, much less play in the first place. Each scene as the hard-hitting pugilist is as fun to watch as it probably was for him to play.

While he only had a couple of scenes, Pitt used stoner charm as helpful couch potato Floyd in director Tony Scott's cult classic "True Romance." Written by future collaborator Quentin Tarantino, Pitt makes the most of his limited screen time, humorously shifting from weirdly helpful to silently resentful in a role that lives among his most memorable.

Pitt earned himself an Oscar nomination for his role as real-life Oakland A's general manager Billy Beane in this Aaron Sorkin-penned drama about how Beane changed the face of Major League Baseball through the use of statistics and math to take his team from awful to competitive, leading to the longest winning streak in MLB history. Pitt is fully within his own skin here, playing Beane as witty, sharp and engaging, making for one of the better sports films concerning a potentially boring subject.

Thanks to director Quentin Tarantino, Pitt dives into full-blown character actor territory in the 2009 revisionist WWII action piece. As Lt. Aldo Raine, better known as Aldo the Apache, Pitt dons a Tennessee accent and sardonic charisma as the leader of the Basterds (a group of Jewish-American guerrilla soldiers) who have a mission to kill as many Nazis as humanly possible. Were it not for Christoph Waltz's star-making turn as Nazi officer Hans Landa taking all the attention, Pitt may have earned more attention come awards season than he received.

Outside of his later film with director David Fincher, Pitt’s performance in "Se7en" as rookie detective David Mills qualifies as his most memorable role, paired alongside Morgan Freeman as the pair races against time to piece together a macabre puzzle leading to serial killer known only as John Doe (Kevin Spacey). The game of cat and mouse leads to one of the more memorable endings in film history — and certainly one of Pitt's more memorable quotes. Once the final act unfolds, it's Pitt's performance that serves as an avatar of the audience once the film's devastating conclusion hits like a ton of bricks.

In 1995, Pitt made notices with "Se7en," but as solid as his performance was there, it pales in comparison to his turn as Jeffrey Goines, a mentally ill man with an agenda in Terry Gilliam's "12 Monkeys" starring opposite Bruce Willis. Here, Pitt delivers a wild-eyed and mysterious performance as a potential threat Willis goes back in time in hopes of stopping. Pitt plays the role of assumed villain with aplomb, making himself a manic foil to Willis in a fashion that might remind one of the relationship between Batman and the Joker.

2019 has been a revival of sorts for Pitt, and at the center of it is his turn as Cliff Booth, stuntman and Man Friday to Leonardo DiCaprio’s has-been TV star Rick Dalton. As Booth, Pitt is the epitome of cool despite a checkered past that he often leans right into. Whether it's in a skirmish with Bruce Lee (Mike Moh) or facing down members of the Manson family, Booth is both calm and powerful in a way that could see Pitt earning a well-deserved Oscar nomination come January. 

Originally a box-office disaster, David Fincher's adaptation of Chuck Palahniuk's acclaimed novel found a second life on home video, creating a near-instant cult classic driven largely by Pitt's anti-hero Tyler Durden. Teamed with Edward Norton as an anonymous office drone looking for meaning in life, the pair create an underground fight club leading to mayhem on a mass scale. Pitt goes for broke as a living id in his most freewheeling performance since "12 Monkeys."

A limited release is the main reason many may not have seen Pitt's performance as Jesse James, but be assured his turn as the legendary outlaw is both dark and seductive, delivering chilling moments strong enough to top our list. Pitt is almost wraith-like as he drifts from scene to scene with a subtle sinister menace that only grows each time he turns on a bit of charm. Whether he's holding a knife to the throat of his future assassin (Casey Affleck) or delivering a cryptic monologue while holding a snake, Pitt's intensity is at its peak. It's a shame more audiences haven't taken a chance on director Andrew Dominik's rumination on the toll celebrity can take in more ways than one.