For the better part of four decades, Brad Pitt has been making movies in Hollywood. But he didn’t start breaking out until he had a very memorable role in Thelma & Louise, which made him a sex symbol in 1991. Pitt could have coasted off his movie star looks, but instead he’s proven to be one of the most resilient actors in the industry as well as savvy producer of film and television. Pitt has worked alongside other top actors and some of the best directors, which has given him a number of unforgettable roles over the years.
This week, Pitt’s latest movie, Wolfs, reunites him with his Ocean’s Eleven co-headliner, George Clooney. The film had a brief stop in theaters before heading to Apple TV+, where it is now streaming. But in honor of Pitt’s new film, it’s time to look back at the seven best Brad Pitt movies.
7. 12 Monkeys (1995)
Brad Pitt has had flashier — and perhaps even better — roles than Jeffrey Goines in 12 Monkeys. But director Terry Gilliam’s dark sci-fi flick is by far one of the best movies that Pitt has ever made. Pitt largely takes a backseat to Bruce Willis, who plays James Cole. James comes from a future where humanity has been nearly wiped out by a plague that may somehow be linked to Jeffrey and his wealthy father, Dr. Leland Goines (Christopher Plummer).
James is sent back in time to determine how Jeffrey and his radical group, the Army of the 12 Monkeys, unleashed an apocalypse. He finds an unexpected ally in Dr. Kathryn Railly (Madeleine Stowe), a psychiatrist who discovers proof that James’ time travel journey isn’t a delusion.
Rent or buy 12 Monkeys on Prime Video.
6. Burn After Reading (2008)
The Coen brothers‘ Burn After Reading features Pitt in one of his funniest roles to date as personal trainer Chad Feldheimer. Through a series of unlikely events, Chad and his co-worker, Linda Litzke (Frances McDormand), discover the manuscript for an autobiography written by ex-CIA agent Osborne Cox (John Malkovich). But Chad and Linda don’t recognize the manuscript for what it actually is, and they believe that they’ve stumbled upon valuable intelligence secrets.
Chad and Linda bumble their way through attempts to blackmail Osborne or sell his info to Russian intelligence agents. George Clooney also has a role in this movie as Harry Pfarrer, the man who is having an affair with Osborne’s wife, Katie Cox (Tilda Swinton). Pitt and Swinton only get to share one scene, and trust us, you’re going to remember it when it comes.
Rent or buy Burn After Reading on Prime Video.
5. Legends of the Fall (1994)
Pitt was still in his peak heartthrob years when he starred in Legends of the Fall, a romantic drama that cast him as Tristian Ludlow, the middle son of rancher Colonel William Ludlow (Anthony Hopkins). Aidan Quinn played Tristian’s older brother, Alfred Ludlow, while Henry Thomas portrayed their younger brother, Samuel Ludlow.
A love triangle emerges when Samuel brings home his bride-to-be, Susannah Fincannon (Julia Ormond), a woman who immediately has eyes for Tristian as well. But as the years unfold, the Ludlows are struck by tragedy, separated by the first World War. By the time the war is over, even Aidan develops feelings for Susannah. It’s emotionally messy at times, but Legends of the Fall is also a gripping family saga that earns its epic status.
Watch Legends of the Fall on Netflix.
4. Moneyball (2011)
By the time Pitt starred in Moneyball, he was comfortably taking roles that reflected his age. In this film, he played Billy Beane, a former baseball player who had never quite managed to be a star. But as the general manager of the Oakland Athletics, the real Billy Beane left his mark on the entire game of baseball.
The movie takes some creative liberties with the real story of how this happened. The short version is that Beane meets Peter Brand (Jonah Hill), an analyst who has come up with a way to accurately identify undervalued baseball players. Using Brand’s methods, Beane puts together the first winning team that the As have had in years. But the true challenge of his Moneyball ideology is if this team can go all the way to the World Series.
Rent or buy Moneyball on Prime Video.
3. Seven (1995)
David Fincher‘s Seven is one of the greatest thrillers of all time, especially because of the ending… which we will not spoil here. Pitt stars as David Mills, a homicide detective who has recently relocated with his wife, Tracy (Gwyneth Paltrow). David is partnered with a veteran detective, William Somerset (Morgan Freeman), who is completely weary about his life and ready to walk away from his career.
Their first case together uncovers an unsettling serial killer who is committing his crimes based on a twisted interpretation of the seven deadly sins. Each murder victim dies in increasingly gruesome ways. And with David and William on his tail, it’s only a matter of time before the killer turns his eye toward them as well.
Watch Seven on AMC+.
2. Once Upon a Time in Hollywood (2019)
In what may be his final collaboration with director Quentin Tarantino, Pitt had a large role in Once Upon a Time in Hollywood as Cliff Booth, an aging stuntman and the personal driver of his friend, Rick Dalton (Leonardo DiCaprio). Aside from Rick, very few people like Cliff, and almost everyone is convinced that he murdered his wife. Yet Cliff is so formidable that even the great Bruce Lee (Mike Moh) has trouble handling him in an impromptu fight.
There are scenes in the movie where Cliff runs afoul of the Manson family that are just dripping with tension. The ways that Cliff defuses those situations are hilariously memorable, and Tarantino’s way of flipping off history.
Watch Once Upon a Time in Hollywood on Hulu.
1. Fight Club (1999)
If we’re going to talk about the very best Brad Pitt movie, then we’re gonna have to break the first two rules of Fight Club. Pitt reunited with Seven director David Fincher for this adaptation of Chuck Palahniuk’s novel. This time, Pitt plays Tyler Durden, the newfound best friend of Ed Norton’s unnamed Narrator. Tyler is brash, outgoing, handsome, and self-assured — all qualities that the Narrator is not. Tyler even seduces Marla Singer (frequent Tim Burton collaborator Helena Bonham Carter), a woman whom the narrator is not particularly fond of.
Together with Tyler, the Narrator co-founds Fight Club, a group that allows men to work out their aggression by beating the hell out of each other. But Tyler isn’t satisfied with that. He wants to launch a revolutionary movement. And by the time the Narrator realizes what’s happening, Tyler has already put his grand plans into motion.
Watch Fight Club on Hulu.