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Despite her prolific career, Angelina Jolie makes headlines nearly as often for her relationships with the likes of Brad Pitt and Billy Bob Thornton as she does her movies and humanitarian work. The Maleficent star’s high-profile marriages (and alleged flings) keep her in the tabloids.

Jolie’s rush to the altar with the Love Actually star in 2000 put them in the spotlight, complete with many unique details of their union. The two were openly passionate about each other. But they divorced just two years later. The Oscar-nominated actor previously shared what drove them apart.

Billy Bob Thornton was engaged to someone else when he married the fourth of his five wives, Angelina Jolie

Angelina Jolie Billy Bob
(L-R) Angelina Jolie and Billy Bob Thornton in 2001. | Gary Friedman/Los Angeles Times via Getty Images

Playing husband and wife in the 1999 movie Pushing Tin, Angelina Jolie and Billy Bob Thornton had an instant connection. Tying the knot in May 2000 in Las Vegas, the couple’s marriage was a particular surprise to Big Little Lies star Laura Dern, who was engaged to Thornton at the time. 

The unlikely pair proceeded to cover magazines, revealing many idiosyncrasies about their unusual celebrity relationship. In addition to Angelina Jolie and Billy Bob Thornton’s 20-year age difference, wearing vials of each others’ blood as necklaces, swapping underwear, and gifting each other with his-and-her grave plots set the couple apart from a typical husband and wife.

”People think they know a lot about our relationship,” Jolie once said, according to the New York Times. ”They know very little. What little they know, they’ve got pretty strong opinions about. Can’t help that. But I don’t think there’s anything weird about us. … I’m just a very normal woman who is crazy about her man. And I’m also a lot of other things.”

How Angelina Jolie and Billy Bob Thornton grew apart

As happens in many marriages, Angelina Jolie and Billy Bob Thornton began to drift apart due to their interests. “He’s a really good man,” she told Vanity Fair in 2015. “I went through a change in my life and started paying more attention to the news and learning about other countries and becoming more politically active.”

With Jolie pursuing humanitarian efforts and Thornton focused on his music, the couple grew apart to the point of no return. “In a year I became who I am today, very much, and he became who he is today,” she explained.

Perhaps because of how old Angelina Jolie was when she dated Billy Bob Thornton — just 24 when they tied the knot — she states they were on “totally different paths in life.” “We just looked at each other one day and we had nothing to say to each other,” she noted.

As for the rumors that Thornton cheated on Jolie, “I don’t think they are untrue,” the Tomb Raider star said. She noted that Thornton didn’t want to commit to expanding their family, though they’d planned to adopt her son, Maddox, together. “He wasn’t, uh, ready, but, uh, he sent me his love. It’s kind of tragic.”

How Angelina Jolie and Billy Bob Thornton feel about each other now

Jolie still held Thornton in high regard, sharing how they simply went from being in sync to going on different paths. But the Bad Santa actor seemed a little more bewildered shortly following their breakup, unable to pin down specific reasons for their divorce.

”I don’t think either one of us knows why we split up,” he said in 2003, according to Entertainment Weekly. ”It was like, say you’re going to a nightclub one night with your friends and you’re in line and the next thing you know there are guys with helicopters and there’s machine-gun fire and you don’t know what happened. And that’s kind of like what our breakup was like.”

The couple maintains a strong friendship to this day. In a 2016 interview with GQ, Thornton expressed his continued fondness of Jolie yet admitted, “I never felt good enough for her.”