The Maleficent star shares her six children with one of her ex-husbands
Angelina Jolie reigns supreme as one of the most magnetic stars in Hollywood, having occupied a space in the public consciousness for over four decades.
Alongside her celebrated film career and humanitarian work, however, her love life has been the subject of much coverage and speculation, given her relationships with some of the industry's leading men.
Teen Love
Angelina, now 48, has spoken about her boyfriend as a teenager when she was 14, which she'd compared to a "marriage" in an interview with the Calgary Sun.
In fact, her boyfriend had moved with her into her mother Marcheline Bertrand's home, where they remained for two years.
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"We were together and serious for two years," she remarked. "That relationship felt like a marriage. It was a tough breakup, so I immersed myself in acting to get over it."
Jonny Lee Miller
In 1995, Angelina embarked on her first relationship since her teenage breakup when she entered a romance with her co-star, English actor Jonny Lee Miller.
After production on the film ended, they lost touch, but reconnected months later and tied the knot in 1996, and the actress famously showed up for their wedding in rubber pants and a white tee with the groom's name in blood.
Sadly, their romance was not to last, and they separated a year and a half later. Their divorce was finalized in early 2000, but they remained friends after their separation.
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Jenny Shimizu
When she'd lost touch with Jonny, she entered into a relationship with American actress and model Jenny Shimizu, which began on the set of their 1996 movie .
In a 1997 interview, she confirmed the romance, saying: "I probably would have married Jenny Shimizu if I hadn't married my husband. I fell in love with her the first second I saw her… She's great. We had a lot of fun."
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Jenny claimed in a later interview that their relationship continued for years after, even during Angelina's marriages, which the actress never confirmed. However, she openly stated years later that she did in fact consider herself to be bisexual.
Timothy Hutton
While less notable than her others, Angelina reportedly dated her (1997) co-star Timothy Hutton in 1996 while they were making the film, soon after her separation from Jonny.
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It's unclear how long their relationship lasted, however it apparently was ongoing when in 1999, she met…
Billy Bob Thornton
On the set of the movie , Angelina met the American actor and filmmaker, although they didn't pursue a romance at the time due to her relationship with Timothy and his with actress Laura Dern.
They soon got together and got married in 2000, with their public displays of affection receiving much attention, including the infamous wearing of the vials of each other's blood round their necks.
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They planned to adopt a child together from Cambodia in 2002, but abruptly separated three months later, and were divorced by 2003. Angelina went through with the adoption solo, welcoming son Maddox, now 22.
Brad Pitt
Angelina and Brad Pitt's legendary love story controversially began on the set of 2005's , which was plagued with accusations of infidelity leading to Brad's divorce from Jennifer Aniston.
Both actors have maintained that they never took that extra step, and kept coy about their relationship till January 2006, when she confirmed they were expecting their first child together, welcoming daughter Shiloh, now 17, later that year.
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They were dubbed "Brangelina" and became Hollywood's ultimate power couple, thanks to their joint A-list status, acclaimed work, and large family (they were the parents of six children while together, including two Angelina had adopted before Shiloh's birth).
They announced their engagement in April 2012 and tied the knot twice in August 2014. However, they separated in 2016 and were declared legally single in 2019, although their divorce and division of joint properties has remained contentious ever since.
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