Billy Bob Thornton Dating History: What Most People Get Wrong

Billy Bob Thornton is a lot of things. Oscar winner. Musician. Guy who once famously survived on nothing but potatoes. But honestly, if you look at the Billy Bob Thornton dating history, it’s a chaotic, fascinating roadmap of a man who spent decades trying to figure out how to be a partner without feeling like a "caged lion." He’s been married six times. Six. That’s a number that gets him compared to Elizabeth Taylor or Henry VIII, depending on who you ask.

Most people only remember the vials of blood and the tattoos. They remember the whirlwind with Angelina Jolie that seemed to dominate every tabloid at the checkout counter in the early 2000s. But there is so much more to the story than just the "vampire" phase. From high school sweethearts in Arkansas to a quiet, twenty-year-plus partnership with a special effects artist, Thornton’s romantic life is less about "womanizing" and more about a guy who kept hitting the reset button until he finally found a pace that didn't make him want to run for the hills.

The Early Arkansas Years and the "Struggling Actor" Marriages

Long before he was a household name, Billy Bob was just a kid from Hot Springs, Arkansas. His first marriage was to Melissa Lee Gatlin in 1978. They were young. He was only 22. They had a daughter, Amanda, but the marriage didn't even make it to the three-year mark. Melissa eventually cited "incompatibility and adultery" in the divorce papers. It was a messy start to what would become a very public pattern.

Then came the 80s. Billy was in LA, starving, working telemarketing jobs and eating those famous potatoes. In 1986, he married Toni Lawrence, an actress you might recognize from old shows like McCloud. It lasted about two years. Toni later told People magazine that he was "very troubled" back then. Basically, he hadn't found his footing yet, either in his career or his head.

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Marriage number three was to Cynda Williams in 1990. This one is interesting because she actually starred in his breakout writing debut, One False Move. By the time the movie actually hit theaters in 1992, they were already divorced. Cynda later joked that they were basically just friends and had no business getting married in the first place.

The Pietra Dawn Cherniak Era: Things Get Intense

In 1993, Thornton married Pietra Dawn Cherniak, a Playboy model. This is where the public perception of Billy Bob started to shift from "eccentric artist" to "volatile personality." They had two sons together, Harry James and William Langston.

The split in 1997 was anything but civil. Pietra filed for a restraining order, alleging domestic abuse. Thornton vehemently denied everything, but the damage to his reputation was significant. It was a dark chapter. It also set the stage for the most famous "almost" marriage in his history: his relationship with Laura Dern.

The Laura Dern and Angelina Jolie "Switch"

If you want to know why people were so obsessed with the Billy Bob Thornton dating history in the year 2000, you have to look at how he ended things with Laura Dern. They were engaged. They lived together. They had a dog. Then, Laura went away to film a movie.

While she was gone, Billy Bob went to Vegas and married Angelina 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 famously told Talk magazine.

It was a "sudden death" of a relationship. No closure. No phone call. Just a headline.

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Then came the Jolie years. They met on the set of Pushing Tin. She was 24; he was 44. It was pure, unadulterated Hollywood chaos. They wore those lockets. You know the ones. For years, the rumor was they were "vials" of blood. Billy Bob recently cleared this up in a 2025 interview, explaining they were just tiny lockets with a single drop of blood smeared inside. "By the time the press was done with it, we were vampires living in a dungeon," he joked.

They were inseparable until they weren't. They planned to adopt a child (Maddox) from Cambodia, but by June 2002, they had separated. Billy Bob has since said they simply had "lifestyles that were too different." She wanted to save the world; he wanted to watch baseball and play music.

Why Connie Angland is the One Who Lasted

After the Jolie divorce was finalized in 2003, everyone expected Billy Bob to find "Number Six" immediately. Instead, he met Connie Angland on the set of Bad Santa. She was a puppeteer and special effects artist. She wasn't an A-list actress looking for a red carpet partner.

They started dating in 2003. They had a daughter, Bella, in 2004. But Billy Bob swore he’d never marry again. He told Maxim in 2008 that he didn't want to put Connie through the "press circus" of being his next wife. He stayed true to that for a long time. They were together for eleven years before they finally, quietly, tied the knot in October 2014.

The Current State of Affairs (2026)

As of January 2026, Billy Bob and Connie are still going strong. That’s over 22 years together—longer than all his other marriages combined. He’s currently starring in Landman, and while rumors occasionally pop up about him being "too close" to his ex, Angelina (they are still best friends), Connie seems to be the anchor he never had.

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He recently joked on a talk show that Connie bought a house with a recording studio just to keep him from driving to hotels when they have a spat. It’s that kind of low-key, real-world dynamic that seems to have finally "tamed the lion."

What We Can Learn from the Billy Bob Timeline

• Marrying young (or for the wrong reasons) rarely works. Thornton admitted that some of his early marriages were just because someone said, "Hey, we should get married," after a few drinks.
• Lifestyle compatibility is everything. You can love someone (like he loved Jolie), but if one person wants to travel the globe and the other wants to stay home, the "official" nature of marriage will eventually feel like a cage.
• Privacy is a relationship saver. By waiting a decade to marry Connie and keeping their ceremony private, Thornton avoided the "vampire" narrative that killed his previous high-profile romances.

If you're looking at your own relationship history and feeling like a failure, just remember: it took Billy Bob Thornton six tries and fifty years to find the one that actually fit. Sometimes the best "dating history" is the one that finally stops moving.

Check out Billy Bob's recent work in Landman on Paramount+ to see how he's channeling that grizzled, settled energy into his newest roles.