The Fargo actor and the stunning Oscar winner had a whirlwind romance, tying the knot in Las Vegas following a two-month courtship. The PDA-friendly couple, who famously wore each other's blood around their necks, divorced in May 2003.
Brad and the Friends star wed in July 2000 in a private ceremony in Malibu. Five years later, the pair announced their separation in January 2005 and divorced ten months later.
The Fight Club hunk began a highly-publicized relationship with the Shakespeare in Love actress after the pair costarred in Se7en. The A-list duo split in 1997 after three years of dating.
Angie married her Hackers costar in March 1996, but the union was short-lived as the pair separated a year later and officially divorced in 1999.
The Moneyball star clearly has a penchant for dating his costars. He romanced the August: Osage County actress for three years in the early 90s after working with her on Too Young to Die? and Kalifornia.
The World War Z star had a brief fling with the blonde beauty in the late 80s.
The father of six was linked to his Interview With the Vampire costar for a short time in 1994.
Brad found himself in a love triangle in the late 80s after briefly dating his Head of Class costar, who was in the midst of a divorce from boxer Mike Tyson at the time.
The Changeling actress and the Leverage star, who met during the filming of 1997's Playing God, dated for a few years before parting ways.
MORE PHOTOS: Brad & Angie's romance rewind