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 "Ocean's Thirteen". While less lucrative than the first two films, this sequel earned $311 million at the international box office. Pitt's next film role was as American outlaw Jesse James in the 2007 Western drama "The Assassination of Jesse James by the Coward Robert Ford", adapted from Ron Hansen's 1983 novel of the same name. Directed by Andrew Dominik and produced by Pitt's company Plan B Entertainment, the film premiered at the 2007 Venice Film Festival, with Pitt playing a "scary and charismatic" role, according to Lewis Beale of "Film Journal International", and earning Pitt the Volpi Cup award for