How Big Of An Age Gap Did Angelina Jolie And Billy Bob Thornton Have? The List
Angelina Jolie and Billy Bob Thornton's marriage only lasted three years, but the 20-year age gap between them didn't play a part in their split.
By Feb. 8, 2025 12:30 pm EST
Billy Bob Thornton is no stranger to age-gap romances. The "Landman" star is about 15 years older than his fourth wife, Pietra Dawn Cherniak, and about nine years older than sixth and current wife, Connie Angland. However, by far Thornton's biggest age gap was with fifth wife Angelina Jolie, whom he married in May 2000 when he was nearly 45, and she was about to turn 25. Thornton and Jolie certainly seemed eager to prove their commitment to one another, with the latter getting a tattoo of her beau's name, and the pair even wearing vials containing each other's blood on necklaces. They didn't last long, though, and their divorce was finalized in 2003. However, are all age-gap relationships always doomed to fail? We asked an expert to shed some light on what might have gone wrong between Thornton and Jolie, and if the years between them might have played a major part in their split.
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Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, says a significant age gap isn't necessarily a death sentence for a relationship. However, she also says a 20-year gap, such as the one shared by Thornton and Jolie, can be quite difficult to overcome in the long run. "There are differences in activity and interest levels," Trombetti told The List, adding, "Most people in their 20s want to see the world and go clubbing, whereas someone in their 40s is more settled and wants to stay at home ... One of them could be slowing down and gearing up for retirement while another is still taking care of young kids."
Though there were rumors of infidelity on Billy Bob Thornton's part, the real reason he and Angelina Jolie divorced was far less dramatic. By all accounts, the two just grew apart. "In a year I became who I am today ... and he became who he is today, and it was just totally different paths in life," Jolie told Vanity Fair in 2005, echoing what matchmaker Susan Trombetti said about the two simply being at different stages in their respective journeys.
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Thornton echoed Trombetti's words as well while speaking on the Hollywood Foreign Press Association's podcast in 2018. The "Bad Santa" actor explained that he and Jolie had incompatible lifestyles, as she's always been more of a globetrotter, while he's hesitant to leave his bubble. However, Thornton also noted that while marriage wasn't for them, he and Jolie enjoyed their time together, and remained good friends afterwards.
According to Trombetti, being able to accept their differences is likely why Thornton and Jolie stayed on good terms after splitting. "I would say it comes from the intensity of the love these two shared," she explained. "Never forget they were quite passionate with them wearing a vial of each other's blood around their necks. He also seems proud of his connection to her and amazed at who she has become. She respects his career, so it's one of mutual respect, caring, and a different kind of love."
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