The 10 Best Brad Pitt Movies

Exactly when did Brad Pitt become one of our veteran actors? It seems like only yesterday that he popped up in Thelma & Louise, before casually proceeding to become a reliable box office draw and a household name. But now, we can’t deny that Pitt is not only one of the biggest stars in Hollywood, but also one of its most important talents. It’s clear that he’s seeking out more experimental roles which continue to push his boundaries and establish him as a real Hollywood heavyweight.

So how to rank his movies? Pitt is such a big star that no matter how effectively he immerses himself in a role, something about his characters is never quite divorced from the persona of the man playing them. For that reason, combined with his intuitive ability to select the right projects, there’s usually little difference between his best films and his best performances. So here are some of his very finest outings, showcased in 10 great movies.


10. 12 Monkeys (1995) – Terry Gilliam

12 monkeys

It shouldn’t be surprising that a Terry Gilliam film was the arena where Pitt pushed the boundaries of his acting abilities to the max. Attacking this eccentric role with relish, he assured movie fans forever that his range comfortably included the capacity to act downright crazy. Letting go of the restraint and discipline that some may have previously mistaken for lack of versatility, he delivered a carefully unhinged performance to remember.

Terry Gilliam’s time-bending sci-fi is his best effort to please mainstream audiences with his patented brand of weirdness. Featuring a time-traveling hero who travels back to the year 1996 to try and prevent a worldwide pandemic, 12 Monkeys is as fun as it is unconventional. The leader of a group of anarchists who unleashed the virus is the unlikely antagonist, and Brad Pitt handles the role wonderfully. We meet his character in an insane asylum, and his behavior never normalizes for a moment throughout the film. A rare instance of artistic authenticity meeting commercial success, 12 Monkeys is one of a kind.


9. Once Upon a Time in Hollywood (2019) – Quentin Tarantino

Quentin Tarantino and Brad Pitt may not have been the most predictable partnership we could have imagined, but it seems to be working. This director has apparently found a knack for matching this star with the right kind of role in his unorthodox films. Here, Pitt plays the stunt double and wingman to Leonardo DiCaprio’s movie star; but his performance doesn’t play second fiddle to anyone, and this is some of his very best acting.

On the surface, this movie seems very different from Tarantino’s other work, but upon closer inspection it’s very much a creature of his creation. Once Upon a Time in Hollywood is as much a celebration of the mythic, bygone days of Hollywood as its title suggests. Blending real historical characters (like Sharon Tate) with fictional ones (like Cliff, the stunt double played by Pitt), Tarantino fashions an impressive, if romanticized, tribute to the glory days of movie history. Tarantino stirs up no less controversy than usual with his latest film, but it’s also his most mature work to date.


8. Snatch (2000) – Guy Ritchie

Along with 12 Monkeys, this was Pitt’s other best opportunity to cut loose and completely divorce performance from persona. Sure, his accent is unintelligible to most ears, but it’s meant to be that way; and with that kind of freedom, an actor can have a lot of fun. And he certainly does, delivering a freewheeling performance that’s guaranteed to stick with you.

Snatch is a fast-paced, frenetic crime comedy that never slows down long enough for the viewer to fully understand what’s going on. But, that’s the intent, and the film’s execution manages to match its ambition. Pitt plays a rough street fighter who inadvertently gets drawn into the high-stakes world of fixed boxing matches. Meanwhile, the theft of a giant diamond forms an entirely separate plot which constantly threatens the viewer with whiplash; but this is organized chaos, and it’s undeniably fun to watch.


7. Meet Joe Black (1998) – Martin Brest


On the surface, this might seem like Brad Pitt’s easiest role – an emotionally restricted, socially ignorant newcomer to the human race who’s learning as he goes. But Pitt resists the temptation to phone in his performance, however catatonic his acting may appear at times. There’s always an important level of emotionally intelligent nuance lurking just beneath the surface of his measured delivery, and by the end of the film the character must display a depth of feeling that’s unique because of its novelty.

Death Takes a Holiday is the name of the 1934 film that this one was was inspired by, and its title reveals much about its plot. Brad Pitt plays the Grim Reaper himself, who comes to claim the life of a wealthy tycoon with a beautiful daughter. As the figure of Death helps to prepare his new victim, he also starts to fall for the daughter – an experience which introduces him to a whole new world of human emotion. Meet Joe Black is a uniquely touching film, with Anthony Hopkins delivering a brilliant performance to match Pitt’s.


6. Legends of the Fall (1994) – Edward Zwick

Pitt’s role in Legends of the Fall perfectly captures the mid-90’s phase of his career. Cast as a misunderstood rebel who is perennially favored and loved by all (in no small part due to his dashing good looks), his physical presence was a huge selling point that made him a fit for the role. But in this romantic tear-jerker, Pitt also displayed impressive emotional range which foreshadowed the blossoming that his career was about to experience.

Legends of the Fall is a sweeping, multi-generational epic centering on the lives of one family living in early 20th century Montana. Anthony Hopkins plays a retired colonel, jaded and mistrustful of government, who moves his family far away from the madness of “civilized” society. But trouble eventually finds them when one of the three sons brings his fiancée home from college with him. All three brothers fall in love with the same girl, with division and heartbreak soon following. The story escalates into a moving tragedy which director Zwick handles with class.