One of the Greatest
Actors of All Time

The role that defined a generation. Brad Pitt transformed into the anarchist soap salesman who became the ultimate anti-capitalist icon. "The first rule of Fight Club is: you do not talk about Fight Club." He got shredded, he got philosophical, and he made nihilism look cool.

The young, hot-headed detective hunting a serial killer who murders based on the seven deadly sins. That ending. That box. Brad Pitt's anguished screaming of "What's in the box?!" became one of the most iconic moments in cinema history. Dark, devastating, perfect.

The coolest heist movie ever made. Pitt as Rusty Ryan — the guy who is always eating, always scheming, always the most effortlessly cool person in any room. He made eating shrimp cocktail while planning a $160M casino robbery look like the most natural thing in the world.

Brad Pitt plays the Oakland A's GM who revolutionized baseball with statistics. Oscar-nominated performance. He spends the entire movie eating — chips, sunflower seeds, soda — because the real Billy Beane does that when he is nervous. Which is always.

The role that finally won him the Best Supporting Actor Oscar. Brad Pitt as the laid-back stuntman who feeds his dog, makes mac and cheese, and casually beats up Bruce Lee. Tarantino wrote the role specifically for him. Nobody else could have played it.

An Irish Traveller bare-knuckle boxer with an accent so thick nobody can understand a word he says. Guy Ritchie's chaotic masterpiece gave Pitt one of his most physically entertaining roles. He threw punches, he threw lines, and he stole every scene.

Brad Pitt's production company Plan B produced the film that won Best Picture. He also appeared in a small but pivotal role as Bass, the Canadian carpenter who helps Solomon Northup gain his freedom. He used his star power to get this essential story made.

Another Plan B production, another Best Picture winner. Pitt plays the reclusive, paranoid ex-trader who helps two young investors bet against the housing market. He eats organic food, worries about chemicals, and delivers the moral weight of the entire film.