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.
They called off their engagement seven months after he proposed. I wasn't ready, and he was too good for me." Jennifer Aniston, 1998 – 2004.
Hollywood heart throb Brad Pitt has dated everyone from actresses to singers and models.
Or maybe there's a Brad and Jen celebrity sex tape in a closet somewhere from their time together.
Brad Pitt's first wife was Jennifer Aniston, but the seemingly rare successful Hollywood marriage ended in 2005.
It’s no secret that Courteney Cox has gotten a bucket load of plastic surgery, especially since her face is living proof of that.
But I don’t think she expected that her BFF Jennifer would ever be willing to call her out in public like that.