Billy Bob Thornton may be one of Hollywood's most consistently busy stars, but he's also one of its most private. The actor and filmmaker has frequently shared a general disillusionment with celebrity culture and the Hollywood machine, although has always managed to remain in the spotlight not just for his many varied performances, but also his rollercoaster love life. Although at 70, it looks like the star has finally found the lasting love he'd been looking for.
The Oscar winner has been married six times over the last five decades, although at one point, disavowed the idea of it altogether. "Maybe there's something about the official nature of it — maybe it's once there's a paper signed or a door seems closed, then I turn into more of a caged lion or something," he told HuffPost in 2014.
"Landman" star Billy Bob Thornton may have found love now, but it took him six tries to get there
Back in 2003, he shared his marriage advice with People: "go into it with the idea that you want it to last, but don't put pressure on yourself to try to achieve perfection every day, because I think that's when you get into trouble," adding that while it's best to operate with the idea of "forever," don't let it get to the point that it'll "freak you out."
The Landman star has walked down the aisle six times in his life, even welcoming four children with three of his wives. Take a look at Billy Bob Thornton's marital history…
In 1978, a 22-year-old Billy married fellow Arkansas native Melissa Lee Gatlin, and they welcomed a daughter together, Amanda. They divorced two years later, with Melissa citing "incompatibility and adultery" in her divorce petition. In 2008, their daughter was sentenced to 20 years in prison for the death of a friend's toddler daughter, but she was freed in 2020 after reaching a deal with prosecutors.
In 1986, Billy, still struggling to break into mainstream Hollywood, married artist Toni Lawrence, although that marriage ended two years later as well. Toni later told People: "He's really talented, that's obvious now. But…he's very troubled."
In 1990, he married Cynda Williams, an actress starring in his writing debut, 1992's One False Move. They were divorced by the movie's release, with Cynda telling People: "We were just friends; we had no business being married."
In 1993, Billy tied the knot with Playboy model Pietra Dawn Cherniak, 14 years his junior, with the couple welcoming sons William and Harry. Their volatile relationship came to an end in 1997, with Pietra also filing a restraining order against her ex, lobbying domestic abuse allegations that included him hitting her in front of their children (Billy and his team vehemently denied the claims).
In May 2000, 43-year-old Billy married his 24-year-old Pushing Tin co-star Angelina Jolie. The couple often made headlines for their PDA-laden public appearances, and seemingly eccentric behavior, turning heads at the time for wearing vials of each other's blood around their necks. In 2002, the couple began the process of adopting a child together from Cambodia. However, the following year, the pair announced their split and Angelina adopted her son Maddox as a single parent (he was later officially adopted by her next husband, Brad Pitt).
In 2003, Billy began dating makeup artist Connie Angland, who is now 61. They welcomed a daughter together, Bella (who is now an actress herself), in 2004. While the Monster's Ball actor cited his desire never to marry again, it was revealed in 2014 that he and Connie had quietly tied the knot, and they're still together to this day.
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