Brad Pitt

Pitt then had the lead role in 1998's Meet Joe Black. He portrayed a personification of death inhabiting the body of a young man to learn what it is like to be human. The film received mixed reviews, and many were critical of Pitt's performance. According to Mick LaSalle of the San Francisco Chronicle, Pitt was unable to "to make an audience believe that he knows all the mysteries of death and eternity."
• From 1999 to 2003
In 1999, Pitt portrayed Tyler Durden, an uncompromising and charismatic individual, in Fight Club, a film adaptation of Chuck Palahniuk's novel of the same name, directed by David Fincher. Pitt prepared for the part with lessons in boxing, taekwondo, and grappling. To look the part, Pitt consented to the removal of pieces of his front teeth which were restored when filming ended. While promoting Fight Club, Pitt said that the purpose of the film was not necessarily to take one's aggressions out on someone else but rather to "have an experience, take a punch more" and see how you come out on the other end." Fight Club premiered at the 1999 Venice International Film Festival and, despite divided critical opinion on the film as a whole, Pitt's performance was broadly praised. Paul Clinton of CNN noted the risky yet successful nature of the film while Variety remarked upon Pitt's ability to be "cool, charismatic and more dynamically physical, perhaps than ... his breakthrough role in Thelma and Louise". In spite of a worse-than-expected box office performance, Fight Club became a cult classic after its DVD release in 2000.
Following Fight Club, Pitt was cast as an Irish Gypsy boxer with a barely intelligible accent in Guy Ritchie's 2000 gangster film Snatch. Several reviewers were critical of Snatch, however most praised Pitt. Mick LaSalle of the San Francisco Chronicle said Pitt was "ideally cast as an Irishman whose accent is so thick even Brits can't understand him", going on to say that, before Snatch, Pitt had been "shackled by roles that called for brooding introspection, but recently he has found his calling in black comic outrageousness and flashy extroversion;" while Amy Taubin of The Village Voice claimed that "Pitt gets maximum comic mileage out of a one-joke role".