Billy Bob Thornton's romantic history is defined by intense media storms, six distinct trips down the aisle, and a famous marriage to Angelina Jolie that still captures public fascination decades later. While tabloids spent years reducing his love life to gothic caricatures—such as wearing vials of blood around their necks—the reality behind his marriages involves stark differences in lifestyle, rapid-fire romances, and a long-term search for stability.
Long before settling down with his sixth wife, Connie Angland, Thornton navigated a turbulent path through Hollywood. Examining his relationship timeline reveals how youthful impulses, sudden fame, and incompatible life goals shaped six separate marriages.
The Early Years and First Three Marriages
Before achieving mainstream superstardom with Sling Blade, Thornton walked down the aisle three times during a span where his career as a struggling actor and writer was fraught with instability.
- Melissa Lee Gatlin (1978–1980): Thornton married his first wife when he was in his early twenties. The marriage produced a daughter, Amanda, but ended after two years when Gatlin filed for divorce citing incompatibility and adultery.
- Toni Lawrence (1986–1988): His second marriage was to actress Toni Lawrence. The union lasted two years before dissolving quietly, with Lawrence later characterizing him in interviews as exceptionally talented yet deeply troubled.
- Cynda Williams (1990–1992): Thornton married actress Cynda Williams shortly before she starred in his breakout writing project, One False Move. The marriage collapsed by the time the film was released, with both acknowledging they were better suited as friends than spouses.
The Volatile Marriage to Pietra Dawn Cherniak
Thornton's fourth marriage introduced a new level of high-profile intensity. In 1993, he married former model Pietra Dawn Cherniak. The couple welcomed two sons, William and Harry.
Unlike his previous quiet separations, this marriage ended in a bitter public dispute. In 1997, Cherniak filed for divorce and sought a restraining order, leveling serious domestic allegations against Thornton. Thornton and his legal representatives vehemently denied the claims, but the public fallout marked one of the rockier periods of his pre-stardom career.
The Whirlwind Romance With Angelina Jolie
The defining chapter of Thornton's romantic history began in 1999 on the set of the film Pushing Tin. At the time, Thornton was briefly engaged to actress Laura Dern, but a sudden spark with Jolie upended both of their personal lives. Jolie and Thornton married in Las Vegas on May 5, 2000, following a rapid two-month courtship.
The couple became Hollywood royalty overnight, though tabloids quickly hyper-focused on their eccentric public behavior.
The Truth Behind the Blood Vials
Few celebrity myths persist quite like the rumor that Thornton and Jolie acted like vampires. In reality, the infamous blood vials were modest lockets containing a single drop of each other's blood.
Thornton later clarified that the media twisted a simple romantic gesture into a gothic spectacle. Because they spent long stretches apart filming on different continents, the lockets were meant to symbolize connection. By the time the marriage ended, however, public perception had permanently cast them as eccentric outsiders.
Why the Marriage Ended
The divorce in 2003 was remarkably civil behind closed doors, despite public speculation. Thornton has frequently noted that no scandal or betrayal caused the split. Instead, their trajectories pointed in opposite directions.
Jolie embraced a global humanitarian lifestyle and sought to expand her family through adoption, while Thornton grappled with severe anxiety, agoraphobia-like tendencies, and a deep discomfort with high-society circles. Recognizing that their day-to-day lives could not coexist, they parted ways amicably. Both actors maintain mutual respect and a close friendship to this day.
Finding Stability With Connie Angland
Following his divorce from Jolie, Thornton consciously stepped back from high-profile Hollywood dating. In 2003, he began a relationship with makeup effects artist Connie Angland.
Unlike his previous fast-paced romances, this relationship developed quietly over more than a decade. The couple welcomed a daughter, Bella, and chose a low-key lifestyle away from flashbulbs. Though Thornton once maintained that marriage no longer worked for him, he and Angland finally married in a private ceremony in Los Angeles in October 2014. They remain together, marking his longest and most enduring partnership.
Frequently Asked Questions
How many times has Billy Bob Thornton been married?
Billy Bob Thornton has been married six times to six different women. His current wife is Connie Angland.
Why did Billy Bob Thornton and Angelina Jolie divorce?
The marriage ended due to conflicting lifestyles. Jolie pursued a global, public-facing life, whereas Thornton preferred a quiet, private routine and struggled with the demands of intense celebrity culture.
Do Billy Bob Thornton and Angelina Jolie still talk?
Yes. Both actors have confirmed in interviews that they remain close friends and speak periodically despite their split over two decades ago.
How long was Billy Bob Thornton married to Angelina Jolie?
The couple was married for three years, from May 2000 until their divorce was finalized in 2003.
