Angelina Jolie’s early relationship with Billy Bob Thornton became one of Hollywood’s most talked-about romances after the pair met in 1999 on the set of Pushing Tin, leading to an impulsive Las Vegas elopement that captivated the public and media alike. Their whirlwind union, full of passionate and unconventional gestures, offers an intense insight into two stars whose lives collided dramatically before diverging just as swiftly.
The Beginnings of a Notorious Romance
When Angelina Jolie and Billy Bob Thornton crossed paths while filming Pushing Tin in 1999, the chemistry unfolded both on screen and off. Jolie, then an up-and-coming actress having recently separated from Johnny Lee Miller and dating Timothy Hutton, was drawn into a real-life drama with Thornton, who came to the project as a 45-year-old filmmaker, actor, and musician. At the time, Thornton was already engaged to actress Laura Dern, with whom he had shared a relationship for three years.
The sudden turn in their personal affairs shocked those close to them, especially Laura Dern, who said,
“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.”
– Laura Dern, Talk Magazine (2000)
Their surprise elopement in Las Vegas in 2000, while both were romantically linked to other people, made instant headlines. The couple quickly cemented their presence in Hollywood by purchasing a $3 million home together in Los Angeles, and their intense public displays of affection were a constant source of fascination for tabloids and fans alike.
A Relationship Defined by Intensity and Eccentric Gestures
Jolie and Thornton became famous for the vivid and unconventional ways they expressed their affection. The most iconic symbol of their connection might be the necklaces they wore, each holding a small vial of the other’s blood. This act fueled public intrigue and solidified their reputation as a couple marked by extreme passion and disregard for tradition. Thornton once clarified the blood lockets in a discussion with students, stating,
“We were apart a lot because she’s off making Tomb Raider and I’m making Monster’s Ball. We were on opposite ends—we see each other for two weeks and whatever.”
– Billy Bob Thornton, Loyola Marymount University (2014)
He went on to explain the gesture further:
“She thought it would be interesting and romantic if we took a little razor blade and sliced our fingers, smeared a little blood on these lockets and you wear it around your neck just like you wear your son or daughter’s baby hair in one.”
– Billy Bob Thornton, Loyola Marymount University (2014)
This penchant for intense expression didn’t stop there. Both individuals also tattooed each other’s names on their bodies, further sealing their commitment. In interviews, Thornton admitted to exchanging underwear with Jolie and even described intimate encounters in unconventional places, declaring at a movie premiere that they had sex in their car en route to the event. Their behavior, while sometimes subject to public skepticism, exemplified a relationship that embraced risk and spectacle at every turn.
The Reasons Behind Their Breakup
Despite the headline-grabbing passion of their early years, Jolie and Thornton’s relationship became strained as their lifestyles and ambitions pulled them in opposite directions. Just beyond their two-year anniversary, they announced their split in the summer of 2002. Thornton later reflected on their breakup, offering insight into their incompatibility:
“Hers is a global lifestyle and mine is an agoraphobic lifestyle. So that’s really, that’s the only reason we’re probably not still together, maybe. There was a different path in life we wanted to take.”
– Billy Bob Thornton, HFPA in Conversation podcast (2018)
Angelina Jolie echoed his sentiments in a conversation with Barbara Walters, saying,
“[Billy Bob] started focusing on certain things, his music, and different films. I started focusing on traveling a lot, and really wanted to, and knew Cambodia, and really wanted to adopt a child.”
– Angelina Jolie, Barbara Walters interview
Jolie’s interest in humanitarian work was already taking root; she adopted her son Maddox shortly before the split, a decision that would shape her life and public image in the years that followed. Their breakup signified not only the end of a high-profile relationship but also a turning point for both celebrities’ personal journeys.
New Partnerships and Family Evolutions
Following their split, Angelina Jolie’s personal life remained highly publicized. In 2004, she began a relationship with Brad Pitt during the filming of Mr. & Mrs. Smith, a coupling that generated media hysteria given the rumors surrounding Pitt’s divorce from Jennifer Aniston. Pitt famously adopted Maddox, and together, he and Jolie built a large family, welcoming five more children: Pax, Zahara, Shiloh, and twins Vivienne and Knox. Their union, sometimes called “Brangelina,” eventually ended in 2016 after a lengthy partnership and two-year marriage.
Jolie’s career extended into activism, serving as Special Envoy for the United Nations Refugee Agency and founding the Voices of Hope initiative in February 2025, aimed at supporting displaced women and children worldwide through educational and healthcare efforts. Her on-screen work continued as well, including notable projects like Couture and Maria.
Billy Bob Thornton also navigated a new chapter. He starred in a series of films such as Standing on the Shoulders of Kitties and Devils Peak, and achieved critical acclaim for his award-winning role in the Amazon Prime series Goliath, earning two Golden Globe Awards. Thornton remarried in 2014, tying the knot with Connie Angland, and together they have a daughter named Bella.
The Lasting Legacy of Jolie and Thornton’s Relationship
The early relationship between Angelina Jolie and Billy Bob Thornton remains emblematic of Hollywood romance at its most unpredictable and passionate. Their story is often referenced as a benchmark for unconventional celebrity love affairs, and its impact lingers, shaping the narrative arcs of their subsequent lives. From Jolie’s transformation into a global humanitarian and mother of six to Thornton’s enduring presence in film and television, both have carved distinct paths marked by their time together. While their relationship may have ended nearly as abruptly as it began, the legacy of their headline-grabbing intensity and the evolution it sparked continues to capture attention years later.
