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 the 2009 Cannes Film Festival. Pitt played Lieutenant Aldo Raine, an American resistance fighter battling Nazis in German-occupied France. The film was a box office hit, taking $311 million worldwide, and garnered generally favorable reviews. The film received multiple awards and nominations, including eight Academy Award nominations and seven MTV Movie Award nominations, including Best Male Performance for Pitt. He next voiced the superhero character Metro Man in the 2010 animated feature "Megamind". Pitt produced and appeared in Terrence Malick's experimental drama "The Tree of Life", co-starring Sean Penn, which won the Palme d'Or at the 2011 Cannes Film Festival.