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 2005's "Mr. & Mrs. Smith". Pitt's next role came with the biographical comedy-drama "The Big Short", which he also produced. The film was a commercial and critical success. It went on to gross over $102 million worldwide and received positive reviews from critics. The film was nominated for five Academy Awards, including "Best Picture", earning Pitt his third Academy Award nomination as producer. In 2016, Pitt starred in Robert Zemeckis's romantic thriller "Allied", in which he plays a spy assassin who falls in love with a French spy (played by Marion Cotillard) during a mission to kill a German official