Brad Pitt filmography film "Fight Club" (1999) in a role that required him learn boxing, taekwondo, and grappling. A critical and commercial success, the film has since developed a cult status. Pitt portrayed Rusty Ryan in the commercially successful heist film series "Ocean's Trilogy" (2001–07). In 2002, he earned a Primetime Emmy Award nomination for his guest appearance in the sitcom "Friends". Also that year, Pitt started a production company, Plan B Entertainment, whose first release was the epic war film "Troy" (2004), starring Pitt. He played an assassin opposite Angelina Jolie in the commercially successful action comedy "Mr. & Mrs. Smith" (2005).
Brad Pitt as Jeffrey Goines in Terry Gilliam's 1995 science-fiction film "12 Monkeys". The movie received predominantly positive reviews, with Pitt praised in particular. Janet Maslin of the "New York Times" called "Twelve Monkeys" "fierce and disturbing" and remarked on Pitt's "startlingly frenzied performance", concluding that he "electrifies Jeffrey with a weird magnetism that becomes important later in the film." He won a Golden Globe Award for Best Supporting Actor for the film and received his first Academy Award nomination for Best Supporting Actor. The following year he had a role in the legal drama "Sleepers" (1996), based on Lorenzo Carcaterra's novel