The Affair Rumors Landman's Billy Bob Thornton Will Never Live Down

Celebrity cheating rumors are nothing new in Hollywood, but some folks attract more gossip than others. One such star is actor Billy Bob Thornton, who's been rumored to have engaged in several affairs throughout his illustrious career (and six trips down the aisle). The most famous instance is, of course, Thornton's rumored affair with his fifth wife, Angelina Jolie. Their romance supposedly started while he was engaged to actor Laura Dern. "I left our home to work on a movie, and while I was away, my boyfriend got married, and I've never heard from him again," Dern admitted to Talk Magazine in 2000 (via ABC News).

As for how Thornton frames the end of their relationship, that remains a mystery. He hasn't spoken about Dern. However, the former lovers had a near-miss encounter at the 2017 Golden Globes when cameras caught Dern reacting (just barely) to Thornton waltzing past her to accept his best actor award. Safe to say there was no love lost on Dern's part.

But it's not like Thornton and Jolie lived happily ever after. Their two-year marriage and divorce was old news once she started dating Brad Pitt. Despite their short-lived nuptials, Thornton has maintained a friendly bond with Jolie over the years. "She and I are still very, very close friends," he told Rolling Stone in November 2025. "And that was the one that ended up being a really civilized breakup. We simply split up because our lifestyles were so different."

Billy Bob Thornton married to his sixth wife, Connie Angland, in 2014. But they've been together far longer. While speaking with Rolling Stone, he revealed they'd been together 23 years, putting the start of their relationship shortly after the end of his marriage to Angelina Jolie. But despite finally finding his forever love, things haven't been perfect. In 2008, Thornton's team denied a rumor that he'd been cheating on Angland with his "Manure" co-star, Tea Leoni. "Billy and Téa are just friends," said his representative (via Extra). "They recently completed shooting a film together ('Manure')."

Meanwhile, in October 2024, Halle Berry set the record straight about the rumor that she and Thornton weren't exactly acting during their steamy love scene in 2001's "Monster's Ball." While discussing her Oscar-winning performance on the "Armchair Expert" podcast, Berry explained, "We had this very explicit love scene. There's an urban legend that we really were f***ing, and it's just not true." She later added, "It's secretly driven me mad all these years." Thornton, who was still betrothed to Angelina Jolie, agrees with her assessment.

Finally, Johnny Depp also accused his ex-wife, Amber Heard, of sleeping with Thornton during their marriage. Thornton also denied the claims.