Glaringly Obvious Red Flags In Billy Bob Thornton & His Wife Connie's Marriage

Billy Bob Thornton is perhaps best known for his highly publicized (but short-lived) marriage to Angelina Jolie, but these days, he's found lasting happiness and a steady, quieter home life with his sixth wife, Connie Angland. The story of how they got together was unexpected: as Thornton recalled, he had been working on the film "Bad Santa" in 2003 when makeup artist — and Connie's sister — Carrie Angland introduced them to each other. "She said, 'My sister's gonna visit, and I got a feeling that you're really gonna like her,'" Thornton shared on "The Drew Barrymore Show," noting that he met Connie at a time when he was feeling sad and lost in life. They hit it off right away. "We were together within probably a couple of months, maybe," he adds. "Yeah, she kind of drug me out of the gutter, which was awesome." 

After welcoming their daughter Bella in 2004, Thornton and Connie tied the knot in a private ceremony at their Los Angeles home in 2014, marking his sixth marriage. With five divorces already under his belt, the "Sling Blade" actor had learned some hard-earned lessons about marriage: "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," he told People in 2003.

He sure didn't rush into his relationship with Connie. Speaking to Maxim in 2008, Thornton revealed that he didn't see himself ever marrying again after Jolie, as, according to him, he didn't want the press to start labeling his girlfriend as Wife "Number Six." He also, frankly, didn't consider himself particularly great at relationships, telling The Mirror he wouldn't want his daughter Bella to end up with someone like him. His failed relationships and past mistakes aside, though, those aren't the only glaring red flags in his marriage to Connie.

As mentioned, Billy Bob Thornton has been married more times than you might imagine. His first marriage was to a certain Melissa Lee Gatlin, with whom he shares his eldest daughter, Amanda. He then moved on with actor Toni Lawrence in 1986, followed by Cynda Williams in 1990, and Playboy model Pietra Dawn Cherniak in 1993. He and Cherniak shared two sons, William and Harry, before splitting up in 1997. Afterward, he married Angelina Jolie, with whom Thornton co-starred in the comedy-drama "Pushing Tin" in 1999. They divorced in 2003, just after three years of marriage. Shortly thereafter, he met Connie Angland.

Despite previously claiming he didn't want to marry Angland to spare her from the media circus that came with his past relationships, Thornton, in 2014, revealed in a Huffpost Live interview that it was the idea of marriage itself that made him uneasy. "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 mused. In fact, the only reason he and Angland got married at all was for the sake of their daughter, Bella. (At least he was brave enough to admit it.) "We did it for her, really. Because, after a while, it was like, 'Why aren't my mommy and daddy married after 12 years?'" Thornton shared on "The Late Late Show with James Corden" in 2015. "The reason I didn't want to is my marriages were always very short, and I don't like to try to fix things that aren't broken," he added. "I said, 'Look, I got a pretty bad record, and [things] are going fine.'" Sure seems like he really did learn his lesson.

Billy Bob Thornton is surprisingly much older than his current wife. He turned 70 in November 2025, while Connie Angland is reportedly 61 years old as of this writing, putting their age difference somewhere close to a decade. Although that may seem significant, it's hardly unusual given Thornton's history of dating — and marrying — younger women; for instance, his ex-wife Cynda Williams is 11 years younger than him, while his third wife, Piet Dawn Cherniak, is 15 years his junior. His age gap with Angelina Jolie is even larger — almost 20 years! Susan Trombetti, a matchmaking expert and CEO of Exclusive Matchmaking, previously told our sister site The List how Thornton and Jolie's wide age gap probably made things tricky. "There are differences in activity and interest levels," Trombetti said. "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." (Thornton has kind of confirmed this himself.) "One of them could be slowing down and gearing up for retirement while another is still taking care of young kids." 

With him and Angland, though, Thornton claims they fit really well together as, like him, she doesn't really like the spotlight and is a huge homebody. They're also, according to the Oscar winner, really good friends, which is what keeps their relationship solid. "I mean the whole romantic part of it has to be there. But at the base of it has to be a friendship, and we are friends," Thornton explained in a 2025 interview with Fox News Digital. But will their closeness and compatibility be enough to overcome the hurdles their decade-long age difference might bring? Guess only time will tell.

Speaking of being homebodies, another potential red flag in Billy Bob Thornton and Connie Angland's marriage is how seldom they show up together at public events. Since 2003, the actor and animatronic engineer have only made a handful of red carpet appearances, such as the 2015 Golden Globe Awards and the 2022 premiere of "The Gray Man" in Los Angeles. They are, as of this writing, most recently seen together at the screening of his film, "Landman," in 2024 (seen in the above photo). However, at least two experts have argued that just because a celebrity couple likes to keep a lower profile doesn't automatically mean there are issues.

Similar to Brad and Kimberly Williams-Paisley's extremely private relationship, "I don't think fans should be worrying about seeing a celeb couple together in public and using that as a barometer of relationship health," Susan Trombetti suggested. "We know how the media works." Susan Winters, who analyzed Taylor Swift and Travis Kelce's "red flags" for us, also stressed the same thing. "Taking a step back from the limelight doesn't equate to stepping back from the relationship. Sometimes it's just the opposite," she told Nicki Swift in 2025.

Thornton, for his part, has admitted he's learned to shield his relationships from the spotlight following his very public marriage to Angelina Jolie. "When you're in a celebrity marriage ... I had one of those periods, and during that time I found celebrity to be difficult just because of privacy issues," he said on Oprah Winfrey's "Master Class" podcast in 2014. "I just don't fit in that world at all and get really uncomfortable around it." With Angland, things are different. "I'm in a good relationship now and have been for 10 years. We have a beautiful daughter." Hopefully, it stays that way for the rest of their lives.