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His most high profile relationships included Hollywood heavyweights Gwyneth Paltrow and Jennifer Aniston – who he married in 2000 before moving on to Angelina Jolie.Pitt settled down with the Jolie and they were considered a rare Hollywood success.
Pitt and Jolie hit the headlines when they began dating after meeting on the set of Mr and Mrs Smith in 2005 and denied they had hooked up while Pitt was still married to Jennifer Aniston.
Jolie and Pitt are expected to adopt a three-year-old Vietnamese boy Brad Pitt and Angelina Jolie (C) with children (L-R) Pax Jolie-Pitt, Zahara Jolie-Pitt, Knox Jolie-Pitt, Shiloh Jolie-Pitt and Maddox Jolie-Pitt attend the World Premiere of Disney's "Maleficent", starring Angelina Jolie, at the El Capitan Theatre on May 28, 2014 in Hollywood The couple later adopted a third child, Pax, 12, and also had three biological children, Shiloh, 10, and eight-year-old twins Vivienne and Knox.
But the power couple called time on their 12 year relationship with Jolie filing for a divorce on Monday.
His first leading roles in big-budget productions came with the drama films A River Runs Through It (1992) and Legends of the Fall (1994), and horror film Interview with the Vampire (1994).
He gave critically acclaimed performances in the crime thriller Seven and the science fiction film 12 Monkeys (both 1995), the latter earning him a Golden Globe Award for Best Supporting Actor and an Academy Award nomination.
The pair became one of the biggest power couples in Hollywood and had three adopted children, Maddox, Zahara and Pax and three biological children Shiloh and twins Vivienna and Knox.
Jolie filed for divorce in September 2015 with her lawyer revealing the decision had been made "for the health of the family".
Pitt enjoyed a string of brief flings with stars including So Macho singer Sinitta and Mike Tyson's now ex-wife Robin Givens.
Pitt has also suffered rejection and was famously ditched by Christina Applegate at the 1989 MTV Movie Awards and was dumped by Jill Schoelen who called off their engagement after three months.
Pitt met Aniston in 1998 and the couple tied the knot at a private Malibu ceremony in 2000.
They were seen as one of the most solid relationships in Hollywood but Aniston filed for divorce in 2005 citing irreconcilable differences.
Speaking to W Magazine in 2009 he said: “We still check in with each other. Hollywood heart throb Brad Pitt has dated everyone from actresses to singers and models.