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 screened at a special presentation at the 2006 Cannes Film Festival and was later featured at the 2006 Toronto International Film Festival. "Babel" received seven Academy and Golden Globe award nominations, winning the Best Drama Golden Globe, and earned Pitt a nomination for the Best Supporting Actor Golden Globe. That same year, Pitt's company Plan B Entertainment produced "The Departed", which won the Academy Award for Best Picture. Pitt was credited on-screen as a producer; however, only Graham King was ruled eligible for the Oscar win. Reprising his role as Rusty Ryan in a third picture, Pitt starred in 2007's