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Billy Bob Thornton has long captivated audiences with his raw talent and creative range as an actor, writer, director, and musician. From his Oscar-winning performance in Sling Blade (1996)—which he also wrote and directed—to acclaimed roles in Monster’s Ball, Bad Santa, and the hit TV series Fargo, Thornton has proven himself one of Hollywood’s most versatile and unpredictable storytellers.

But while his career has earned him critical acclaim, his personal life has drawn just as much attention. Known for his charm, eccentricity, and self-deprecating humor, Billy Bob has been married six times, a fact he’s often joked about. “I’ve been married five times, and people think that’s some bizarre thing,” he once said before his sixth wedding, per IMDB. “Yet I’ve got buddies who refuse to get married and have sex with 15 people a week. I’m like, ‘Which is better?’ At least I was trying.”

Now happily settled with his sixth wife, the Oscar winner has had a fascinating romantic history that’s included some high-profile relationships, including his whirlwind marriage to Angelina Jolie. Here’s a closer look at Billy Bob Thornton’s six marriages and the women who’ve shared his life over the years.

Melissa Lee Gatlin

Billy Bob Thornton was first married to Melissa Lee Gatlin. The two tied the knot in 1978. While there isn’t extensive public information available about their relationship, they welcomed daughter Amanda (Brumfield) on June 30, 1979. Following her parents’ split in 1980, where Melissa cited “incompatibility and adultery on his part” in the divorce filings, Amanda grew up estranged from her father, and was raised by her mother instead. Notably, Amanda was sentenced to 20 years in prison in 2008 for the death of her friend’s one-year-old daughter. She was released in 2020.

Toni Lawrence

Born on April 4, 1948, Toni Lawrence was an actress whose credits included McCloud (1970), Daddy’s Deadly Darling (1973) and Sole Survivor (1984), according to her IMDB. The romance between the young starlet and Billy Bob was short-lived, as they married in 1986 and went their separate ways two years later. The couple did not welcome any children during their time together.

“He’s really talented, that’s obvious now,” Toni said years later, per PEOPLE. The potter, who remarried and relocated to LA, added, “But, he’s very troubled.”

Cynda Williams

Cynda Williams graced the world on May 17, 1966, in the city of Chicago, Illinois. With her undeniable talent and captivating presence, she made her mark in the entertainment industry as both an actress and a producer. Her breakout performances in acclaimed films such as “One False Move” (1992), “Mo’ Better Blues” (1990), and the recent sensation “Mad As Hell” (2021) have solidified her status as a force to be reckoned with, per her IMDB.

“We were just friends; we had no business being married,” Billy Bob had told People.

Cynda went on to marry film producer Roderick Plummer in 2001 and she posts about their happy life on Instagram. They share a child as well, per her IMDB.

Pietra Dawn Cherniak

Although Pietra Dawn Cherniak is often labeled as a Russian model, she was actually born in Santa Monica, CA on February 9, 1970. The beauty became a Playboy alum as well and married the Goliath actor in 1993. The couple welcomed two children together: William Langston Thorton was born in June 1993 and Harry James Thornton arrived in June 1994.

In April 1997, Pietra, who doesn’t appear to have a social media account, filed for divorce, citing irreconcilable differences. The fourth Mrs. Thornton also asked a state judge for a restraining order against the actor. “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.

Billy Bob vehemently denied the charges, saying in a statement, “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.”

Angelina Jolie

Angelina Jolie dated many A-listers, but her marriage to Billy Bob in 2000 made quite a splash. The former flames met on the sets of the 1999 film Pushing Tin. The thing was, Billy Bob was engaged to actress Laura Dern at the time. They had been together for over two years and even shared a home. However, Billy Bob reportedly left Laura for Angelina. 

The new couple then tied the knot in 2000 in Las Vegas. The Eternals star and her ex-husband were spotted wearing vials of each other’s blood after their wedding. In a candid interview years later, Billy Bob revealed why his former wife wanted to wear a vial of his blood around her neck. 

“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.”

Billy Bob not only fondly recalls the blood necklaces, but also his entire romance with the Tomb Raider actress, which ended in divorce in 2003. “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 told the outlet. “The movies she makes are still things that are important to her … and whether they succeed or fail, she still does what she believes in, and I’ll always respect her for that.”

Angelina would famously go on to be in a relationship with Brad Pitt, welcoming three children. Sadly, she filed for divorce in 2016. On Instagram, she keeps tabs on her humanitarian work.

Connie Angland

Billy Bob certainly has a thing for actresses. In 2014, he married Connie Angland, but they had been dating for 12 years prior after meeting on the set of Bad Santa, and according to PEOPLE, the wedding took place “at their home in Los Angeles during a private ceremony before family.”

Born on 22 October 1964, Connie would go on to find work in Men in Black (1997), Planet of the Apes (2001) and Men in Black II (2002), per her IMDB. She doesn’t appear to have any social media accounts at this time. The couple also have a daughter, Bella Thornton, who was born in 2004. She is the youngest of Billy Bob’s four children.

In 2016, GQ magazine noted a difference between Billy Bob’s relationship with Angelina and his current marriage with Connie. The publication wrote how “Connie is far more his speed. She’s a homebody, just like him, and Bella is homeschooled, so when Billy’s not working, he gets to be at the house with them.”