During filming, he met and began dating his then relatively unknown costar, Gwyneth Paltrow. Both claimed it was “love at first sight.” The two stayed together for two and a half years and were one of Hollywood’s most admired and celebrated couples. Then, in 1997, after a seven-month engagement, the couple split for unknown reasons. In 1995, Pitt starred as a mental patient in Terry Gilliam’s psychological thriller Twelve Monkeys and won a Golden Globe for best supporting actor. He followed with another dark thriller, Sleepers (1996), and Alan J. Pakula’s Devil’s Own with Harrison Ford, before heading to Argentina to film Seven Years in Tibet, an ambitious, seventy million dollar project, which met disappointingly mixed reviews. Unfortunately, his next film, the three-hour plus Meet Joe Black, co-starring Anthony Hopkins, in which he played a very comely version of Death, also inspired little praise. In 1999, after a brief hiatus from the Hollywood hot list, Pitt re-teamed with Seven director, David Fincher, to make Fight Club. The apocalyptic film, also starring Edward Norton, presents an unglamorous Pitt in a disturbing role as leader and recruiter of Fight Club—a bloody diversion for young professional males. Next up for Pitt was the British crime-caper Snatch (2001), costarring Benicio Del Toro and directed by Guy Ritchie. That same year, Pitt starred with Julia Roberts in the romantic comedy The Mexican, teamed with Robert Redford in the thriller Spy Game, and joined an A-list ensemble cast including Roberts, George Clooney, and Matt Damon in Steven Soderbergh's remake of the Rat Pack heist caper Ocean's Eleven. In 2002, he signed on to play the Greek hero Achilles in Warner Bros.' epic Troy. He will also be producing The Madman of Alcatraz, based on the true story of the psychiatrist who treated the infamous Robert "Birdman" Stroud.
A two-time winner of People magazine's "Sexiest Man Alive" title (1995 and 2000), Pitt began dating Jennifer Aniston, star of the TV sitcom Friends, in 1998. Pitt and Aniston were married July 29, 2000, in Malibu, California. The couple lives in Los Angeles.