Looking back at Brad Pitt and Angelina Jolie’s love lives, it’s not entirely surprising that their relationship fizzled out the way it did. After all, they’ve both been in a number of high profile romances — and they certainly didn’t all end well. Take a look back at their love lives here!
Ever since his breakout role in Thelma & Louise, Brad Pitt, 52, has been one of the most eligible bachelors in Hollywood…and there’s a whole handful of women who’ve been lucky enough to date him. When Christina Applegate was just 18 years old, she turned heads by walking the MTV Movie Awards red carpet with Brad — although she notoriously ditched him mid-show for another man. Then, he dated Juliette Lewis from 1990-1993, when she was also a teenager.
The actor’s first huge high-profile relationship, though, was with Gwyeth Paltrow. They met on the movie Se7en in 1994, and got engaged when she was just 24 years old. However, the pair called off the engagement in 1997, which she has since taken responsibility for. Of course, his broken heart was mended in 1998 when he met Jennifer Aniston, 47, and they tied the knot on July 29, 2000. We all know what happened from there: The marriage ended after he met Angelina Jolie, 41, on the set of Mr & Mrs Smith, of course.
Throughout his career, Brad has also been linked to co-stars Robin Givens, Jill Schoelen and Thandie Newton. It may not have worked out with these girls, but at least they can say they spent some time with Brad Pitt, right?!
But Angelina may have even had a more tumultuous past than Brad — she lived with her first boyfriend for two years when she was just 14! Then, she started dating Johnny Lee Miller while filming Hackers in 1994, and although they lost touch after production ended, they wound up getting married in March 1996. The nuptials are infamous because Angie wore Johnny’s name in blood on her shirt — but the two wound up splitting the next year.
The 41-year-old got married again in 2000 after a two-month relationship with Billy Bob Thornton. The two are famous for publicly declaring their love by wearing vials of each other’s blood around their necks, however, their separation and subsequent divorce was abrupt in 2003. She met Brad two years later.
Angie identifies as bi-sexual and dated Jenny Shimizu before marrying Johnny, while she’s also been linked to stars like Val Kilmer and Colin Farrell. Click through the gallery above for a full look at Brad and Angie’s relationship histories!
HollywoodLifers, which of Brad and/or Angelina’s relationships was most shocking to you? Who do you think they each belong with?