Blood vials and estranged relationships: Inside Billy Bob Thornton's six marriages.

Over the years, Billy Bob Thornton has certainly become well known for his acting range and distinctive roles in films like Sling Blade, Bad Santa, Monster's Ball, and, most recently, Landman, a drama series set within the world of oilfields in West Texas.

But beyond his Hollywood career, Thornton's personal life, particularly his romantic relationships, have often garnered as much attention as his professional achievements.

From his high-profile, controversial relationship with Angelina Jolie (remember the blood vials? We'll get to that later) to his contentious split from a former Playboy model, Thornton has had a total of seven high-profile relationships (that we know about) and six marriages.

Watch the trailer for Landman. Article continues after video. 

Here's a look back at Thornton's relationships, including his current marriage to Connie Angland.

Melissa Lee Gatlin.

Billy Bob Thornton was married to his first wife, Melissa Lee Gatlin, from 1978 to 1980. During their brief marriage, they welcomed a daughter, Amanda, who Thornton seemingly remains estranged from.

In 2008, Amanda's life took a dark turn when she was sentenced to 20 years in prison for the death of her friend's one-year-old daughter. However, in 2015, The Innocence Project of Florida took on Amanda's case, arguing that the child's death was an unfortunate accident rather than intentional harm.

After years of legal battles, Amanda was released from prison in 2020 having served eight years of her sentence.

Toni Lawrence.

In 1986, Thornton married Toni Lawrence, an actress best known for her roles in McCloud, Daddy's Deadly Darling, and Sole Survivor.

Thornton and Lawrence were only married for two years before they went their separate ways in 1988. During their time together, the couple did not have any children.

"He's really talented, that's obvious now," Lawrence said about Thornton, years later, as per People. "But, he's very troubled."

Cynda Williams.

Thornton and Williams met on set of One False Move. Image: IRS Media. 

Thornton met his third wife, Cynda Williams, while filming a movie that he had written called One False Move. Williams is an actress, and has starred in films like Better Blues and Mad As Hell. 

After meeting on set, Thornton and Williams quickly got married in 1990. However, by the time the film was released in May 1992, the couple had already divorced. "We were just friends; we had no business being married," Billy Bob told People. 

Pietra Dawn Cherniak.

Cherkniak accused Thornton of spousal abuse during their divorce. Image: Getty. 

Thornton married ex-Playboy model, Pietra Dawn Cherniak in 1993. They welcomed their first son, William, in 1993 and their second, Harry, in 1994.

Thornton and Cherniak divorced in 1997, with Cherniak accusing him of spousal abuse.

"Over the past year, at least once or twice per month, [Thornton] has hit me, pushed me, punched me, bit me or otherwise physically attacked me, sometimes in front of the children," Pietra said in court papers, per PEOPLE. For his part, he claimed "that Pietra's advisers have convinced her to take this malicious and untruthful course of action."

"Our marriage was not perfect, but I never exhibited the behavior she's accusing me of. Our concerns right now should be about our sons, who will suffer the most as a result of her advisers' conduct," he claimed.

Laura Dern.

Thornton started dating Dern in 1997. Image: Getty. 

Actress Laura Dern is the only woman on this list who was not married to Thornton. However, the two were engaged and had a fairly controversial breakup.

Following his divorce from Cherniak, his fourth wife, Thornton started dating Dern in 1997. However, in 1999, things got very messy when Thornton met Angelina Jolie on set of Pushing Tin.

In 2000, while still engaged to Dern, Thornton secretly married Jolie.

"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 said in 2000, per ABC. "It's like a sudden death. For no one has there been any closure or clarity."

Angelina Jolie.

Jolie and Thornton famously wore viles of each other's blood on necklaces. Image: Getty. 

Arguably, Thornton's most famous marriage was to actress Angelina Jolie. The two were together from 2000 to 2002, and it was contentious right from the start. Putting aside the controversial beginning of their relationship and the 'Laura Dern' of it all, Thornton and Jolie shared a 20-year age gap. She was just 25, while he was 45.

In 2001, Thornton and Jolie made headlines again with their infamous 'blood vial' necklaces. Headlines claimed they literally wore vials of each other's blood around their necks and, understandably, a lot of people were concerned.

Years later, in 2018, Thornton spoke about the entire ordeal and explained it was not nearly as dramatic as it was reported to be at the time.

"The necklaces were a very simple thing. 'Hey, let's poke our finger with a pin and smear a little on there, and when we're away from each other, we'll wear the necklace,'" he told the HFPA Golden Globe podcast in 2018.

"That was that easy, but by the time it came out in the press: it sounded like we were wearing a bucket of blood around our necks. That was a great time."

He also maintained that the two still share a friendship, years after their divorce.

"I look at that time as a great time 'cause, you know, Angie is still a friend of mine and she's a great person," he said.

In March 2002 the pair announced the adoption of a child from Cambodia, but when they separated in June 2002 it was revealed Angelina had adopted the child, Maddox, as a single parent.

Connie Angland.

Thornton met his now-wife on set of Bad Santa. Image: Getty. 

Shortly after his divorce from Jolie, Thornton met his now-wife Connie Angland on the set of Bad Santa in 2003. Angland's sister was a makeup artist on set and introduced the two.

"And we were together within probably a couple of months maybe. She kind of [dragged] me out of the gutter, which was awesome,'" Thornton said on The Drew Barrymore Show in November 2024. "We've been together longer than if you totalled up all the other five [marriages], it's more time."

While Thornton had previously expressed that he and Connie were not interested in getting married, they eventually tied the knot in 2014. He claims it was largely because of their daughter, Bella, who was born in 2004.

"After a while, it was like, 'Why aren't my mommy and daddy married after 12 years?'" he said 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. I said, 'Look, I got a pretty bad record, and things are going fine.'"

Feature Image: Getty.