In 1999, Pitt portrayed Tyler Durden 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 film explored not taking one's aggressions out on someone else but 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.
Despite divided critical opinion on the film as a whole, Pitt's performance was widely 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.

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".
The following year Pitt starred opposite Julia Roberts in the romantic comedy The Mexican, a film that garnered a range of reviews but enjoyed box office success.
Pitt's next role, in 2001's $143 million-grossing Cold War thriller Spy Game, was as Tom Bishop, an operative of the CIA's Special Activities Division, mentored by Robert Redford's character.
Mark Holcomb of Salon.com enjoyed the film, although he noted that neither Pitt nor Redford provided "much of an emotional connection for the audience".

On November 22, 2001, Pitt made a guest appearance in the eighth season of the television series Friends, playing a man with a grudge against Rachel Green, played by Jennifer Aniston, to whom Pitt was married at the time.
For this performance he was nominated for an Emmy Award in the category of Outstanding Guest Actor in a Comedy Series.
In December 2001, Pitt played Rusty Ryan in the heist film Ocean's Eleven, a remake of the 1960 Rat Pack original.
He joined an ensemble cast including George Clooney, Matt Damon, Andy García, and Julia Roberts.
Well received by critics, Ocean's Eleven was highly successful at the box office, earning $450 million worldwide.
Pitt appeared in two episodes of MTV's reality series Jackass in February 2002, first running through the streets of Los Angeles with several cast members in gorilla suits, and participating in his own staged abduction in another episode.
In the same year, Pitt had a cameo role in George Clooney's directorial debut Confessions of a Dangerous Mind.
He took on his first voice-acting roles in 2003, speaking as the titular character of the DreamWorks animated film Sinbad: Legend of the Seven Seas and playing Boomhauer's brother, Patch, in an episode of the animated television series King of the Hill.
In 1999, Pitt portrayed Tyler Durden 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 film explored not taking one's aggressions out on someone else but 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. Despite divided critical opinion on the film as a whole, Pitt's performance was widely 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.
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". The following year Pitt starred opposite Julia Roberts in the romantic comedy The Mexican, a film that garnered a range of reviews but enjoyed box office success. Pitt's next role, in 2001's $143 million-grossing Cold War thriller Spy Game, was as Tom Bishop, an operative of the CIA's Special Activities Division, mentored by Robert Redford's character. Mark Holcomb of Salon.com enjoyed the film, although he noted that neither Pitt nor Redford provided "much of an emotional connection for the audience".
On November 22, 2001, Pitt made a guest appearance in the eighth season of the television series Friends, playing a man with a grudge against Rachel Green, played by Jennifer Aniston, to whom Pitt was married at the time. For this performance he was nominated for an Emmy Award in the category of Outstanding Guest Actor in a Comedy Series. In December 2001, Pitt played Rusty Ryan in the heist film Ocean's Eleven, a remake of the 1960 Rat Pack original. He joined an ensemble cast including George Clooney, Matt Damon, Andy García, and Julia Roberts. Well received by critics, Ocean's Eleven was highly successful at the box office, earning $450 million worldwide. Pitt appeared in two episodes of MTV's reality series Jackass in February 2002, first running through the streets of Los Angeles with several cast members in gorilla suits, and participating in his own staged abduction in another episode. In the same year, Pitt had a cameo role in George Clooney's directorial debut Confessions of a Dangerous Mind. He took on his first voice-acting roles in 2003, speaking as the titular character of the DreamWorks animated film Sinbad: Legend of the Seven Seas and playing Boomhauer's brother, Patch, in an episode of the animated television series King of the Hill.
Brad Pitt