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 film production company he had founded two years earlier with Jennifer Aniston and Brad Grey, CEO of Paramount Pictures. "Ocean's Twelve" earned $362 million worldwide, and Pitt and Clooney's dynamic was described by CNN's Paul Clinton as "the best male chemistry since Paul Newman and Robert Redford." In 2005, Pitt starred in the Doug Liman-directed action comedy "Mr. & Mrs. Smith", in which a bored married couple discover that each is an assassin sent to kill the other. The feature received reasonable reviews but was generally lauded for the chemistry between Pitt and Angelina Jolie, who played his character's wife