Billy Bob Thornton, Gwyneth Paltrow, Christina Applegate and More: A Look Back at Brad Pitt and Angelina Jolie's Famous Exes

by Desiree Murphy 11:08 AM PDT, September 24, 2016
Playing Billy Bob Thornton, Gwyneth Paltrow, Christina Applegate and More: A Look Back at Brad Pitt and Angelina Jolie's Famous Exes

Long before Brad Pitt and Angelina Jolie became one of Hollywood's most beloved couples, they were living separate lives with different people, while rising to fame in the acting world.

The duo, who announced they were divorcing after two years of marriage on Tuesday, has had their fair share of hot hookups. From fast flings with co-stars to real-life romances, ET is breaking down Pitt and Jolie's famous arm candy over the years.

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Brad Pitt and Jennifer Aniston, 1998-2005

Photo: Getty Images

When Pitt fell in love with Jolie on the set of Mr. and Mrs. Smith, he was still married to Aniston. The two said "I do" in Malibu, California, in 2000, after dating since 1998 when they were set up on a blind date by both of their agents. "I have to think there's some reason I have called this into my life," Aniston revealed to Vanity Fair in Sept. 2005, her first interview following the split. "I have to believe that -- otherwise it's just cruel."

Angelina Jolie & Billy Bob Thornton, 1999 – 2003

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Jolie met Thornton on the set of 1999's Pushing Tin. They dated for two months before saying "I do," later divorcing in 2003. "It was a crazy time," the actor told The Hollywood Reporter of their whirlwind romance in Oct. 2014. "I've never been fond of it."

Brad Pitt and Christina Applegate, 1989

Photo: Getty Images

After dating Pitt briefly, the Bad Moms star (who also played Aniston's sister on Friends) took the actor as her date to the MTV Movie Awards in 1989, but ditched him to hang out with another guy! During her appearance on Watch What Happens Live last August, she admitted that was the end to their short but sweet relationship (she has yet to reveal who the other guy was).

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Brad Pitt and Gwyneth Paltrow, 1994-1997

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Young love! This adorable duo met in 1994 while on the set of Seven. Two years later, Pitt proposed to the actress, but ultimately called off their engagement in 1997. Back when the pair was head-over-heels for each other, Pitt told ET popping the question to Paltrow was "one of the greatest moments" of his life. "I guess I'm gonna be a dad with a lot of kids," he said at the time.

Angelina Jolie & Jonny Lee Miller, 1995-1999

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After meeting and falling for her Hackers costar in 1995, her first real relationship since her early teens, Jolie and Miller eloped in Las Vegas in 1996. Unfortunately, things didn't work out and they ultimately called it quits. According to an interview Jolie did with Buzzfeed in May 2014, the two are still "great" friends. "I think of [Jonny] when I think of that [film]," she dished. "Although, I'm sure the movie looks so ancient now, but we had a lot of fun making that."

Brad Pitt and Robin Givens, 1986-1987

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One of Pitt's earliest public relationships was with Mike Tyson's ex-wife, and his Head of Class co-star. The actress was criticized for divorcing the professional boxer, but joked that dating Pitt helped ease the pain. During an interview with Huffington Post Live in January 2013, Tyson explained that in the midst of his divorce from Givens, they were "still having sex" -- until he saw Pitt in the passenger's seat of her car one day.

Brad Pitt and Jill Schoelen, 1989

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Cutting Class was not only the film that featured Pitt in his first starring role, it's also where he met his reported first fiancée. The pair dated for a short three months before he was rumored to ask the actress to marry him. Shortly after, Schoelen called it off when the two were in Budapest, Hungary. "I got there, went straight to the set where she was filming [The Phantom of the Opera] and that night we went out to dinner," Pitt recalled to The Sun in April 2011. "She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here.

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Angelina Jolie & Jenny Shimizu, '90s and '00s

Photo: The Samuel Goldwyn Company

Jolie dated the actress on-and-off for several years in the '90s and early '00's, after meeting during a casting for Foxfire. "I fell in love with her the first second I saw her," Jolie explained in a 1997 interview with Girlfriends magazine. "We had a lot of fun. I probably would have married Jenny Shimizu if I hadn't married my [first] husband."

Brad Pitt and Juliette Lewis, 1989-1993

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After working together in Too Young to Die? and Kalifornia, the two decided to become more than just close co-stars. Their relationship lasted for about four years, but while chatting with the Huffington Post in Sept. 2014, Lewis said she's amazed that people still find their romance fascinating, all these years later. "Whenever I get asked Brad questions, I'm like, 'Do you want to talk about my seventh-grade crush?' Because that was my boyfriend too," she joked.

Angelina Jolie & Colin Farrell, 2004

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While this romance was never confirmed by either party, the two were rumored to be hooking up before Jolie gave Pitt a shot at love. The actress was reportedly infatuated with Farrell on the set of their film, Alexander, but he apparently wasn't feeling a relationship with her and put a stop to their fling during a press tour for the movie.

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