Fight Club (1999) - Pitt plays Tyler Durden, a charismatic anarchist who forms an underground fight club with the film's protagonist.
Inglourious Basterds (2009) - Pitt portrays Lieutenant Aldo Raine, the leader of a group of Jewish-American soldiers on a mission to kill Nazis in German-occupied France during World War II.
Se7en (1995) - Pitt stars as Detective David Mills, who teams up with a veteran detective to track down a serial killer who uses the seven deadly sins as motifs in his murders.
Once Upon a Time in Hollywood (2019) - Pitt plays Cliff Booth, a stunt double to a fading TV star in 1969 Los Angeles, in Quentin Tarantino's homage to the golden age of Hollywood.
The Curious Case of Benjamin Button (2008) - Pitt stars as Benjamin Button, a man who ages in reverse, experiencing life's joys and sorrows in a unique and poignant way.
Moneyball (2011) - Pitt portrays Billy Beane, the real-life general manager of the Oakland Athletics baseball team, who revolutionizes the game by using statistics to assemble a competitive team on a limited budget.
Troy (2004) - Pitt takes on the role of the legendary Greek warrior Achilles in this epic adaptation of Homer's Iliad, which depicts the siege of Troy.
Ocean's Eleven (2001) - Pitt is part of an ensemble cast in this stylish heist film, playing Rusty Ryan, a suave and skilled con artist who helps lead a team of thieves in robbing three Las Vegas casinos simultaneously.
Snatch (2000) - Pitt delivers a memorable performance as Mickey O'Neil, an Irish Traveller and bare-knuckle boxing champion, in this fast-paced crime comedy directed by Guy Ritchie.
Twelve Monkeys (1995) - Pitt earned an Academy Award nomination for his role as Jeffrey Goines, a manic and eccentric mental patient, in this mind-bending science fiction film about time travel and the apocalypse.