Billy Bob Thornton's Love Life: A Timeline Of Marriages & Affairs

Elissa Schiller 18 May 2025

Is Hollywoods most captivating enigma defined by his six marriages, his Oscar win, or perhaps, his enduring ability to remain utterly unpredictable? Billy Bob Thornton, the man who has danced through the spotlight with a quiet intensity, leaves an indelible mark on the landscape of cinema and relationships alike.

From the sun-drenched landscapes of Hot Springs, Arkansas, where he was born William Robert Thornton, Jr. on August 4, 1955, to the glittering red carpets of Hollywood, Thornton's journey has been anything but ordinary. His roles, as varied as they are memorable, have etched his name into the annals of cinematic history. From the gritty realism of "One False Move" (1992), where he portrayed Ray Malcolm with unnerving precision, to the darkly comedic heart of "Sling Blade" (1996), which he wrote, directed, and starred in, earning him an Academy Award for Best Adapted Screenplay, Thornton has consistently defied expectations.

Beyond the silver screen, Thorntons personal life has been equally compelling, a tapestry woven with relationships that have captured the public's imagination. His romantic history is a topic of constant fascination, especially his marriages. This is a man who, as he himself once quipped, had an intention to stop at five weddings, only to find himself at the altar a sixth time. This remarkable life and his marriages offer a glimpse into the complex man behind the roles. His relationships, particularly those with prominent figures like Laura Dern and Angelina Jolie, have been scrutinized and celebrated in equal measure. His marriages and his relationships are as fascinating as his work on screen.

Attribute	Details
Full Name	William Robert Thornton, Jr.
Date of Birth	August 4, 1955
Place of Birth	Hot Springs, Arkansas, USA
Age	69 years old (as of May 18, 2024)
Occupation	Actor, Filmmaker, Musician
Known For	"Sling Blade," "One False Move," "Pushing Tin," "Monster's Ball," "Landman"
Marriages	Melissa Lee Gatlin (19781980), Toni Lawrence (19861988), Cynda Williams (19901992), Pietra Thornton (19931997), Angelina Jolie (20002003), Connie Angland (2014present)
Children	4
Awards and Recognition	Academy Award (Best Adapted Screenplay for "Sling Blade"), Golden Globe nominee (2025)
Relationship with Laura Dern	Dated from 1997-1999, engagement in 1999.
Relationship with Angelina Jolie	Married from 2000-2003, met on the set of "Pushing Tin" (1999).
Notable Collaborations	Has worked with directors such as John Lee Hancock, James Mangold, and many others.
Website	IMDb

Thornton's path to stardom wasn't a straightforward ascent. Before becoming a celebrated actor, he held various jobs, from telemarketing to working at a fast-food restaurant. His early experiences provided him with a unique perspective, which he has infused into his performances. The rawness and authenticity he brought to roles like Karl Childers in "Sling Blade" stemmed from his dedication to understanding the human condition.

His relationship with actress Laura Dern, which began in 1997 after they met on the set of the film "U Turn," was a significant chapter. Their engagement in 1999 hinted at a future together, yet it never materialized. Instead, Thornton's path took an unexpected turn when he met Angelina Jolie on the set of "Pushing Tin" in 1999. This encounter led to a whirlwind romance, culminating in their marriage in 2000, a union that captivated the world. The pair dated for a year after getting together on March 5, 2000, and were married on May 5, 2000. However, this marriage, like others before it, was destined to be short-lived; the couple divorced on May 27, 2003, after three years of marriage.

Thornton's six marriages offer a glimpse into his evolving personal life. Before Jolie, there were Melissa Lee Gatlin, Toni Lawrence, Cynda Williams, and Pietra Thornton. After Jolie, he would later find love again with Connie Angland, whom he married in 2014. Each relationship, it seems, has left its imprint on him, shaping the man he is today. These unions often reflected his willingness to take risks, both in his career and his personal life.

The actor's career has been filled with many memorable performances. In "Sling Blade" (1996), he both wrote and directed, along with starring in the film, earning him an Academy Award. His portrayal of Karl Childers, a man with developmental disabilities, was both tender and unsettling, a testament to his skill. His career began to see its rise in 1986 with his role in the action thriller "Hunter's Blood" as Billy Bob. Then in 1992, he starred in the crime thriller film "One False Move" as Ray Malcolm.

His ability to embody a range of characters has made him a sought-after actor in Hollywood. In 1999, Thornton and Angelina Jolie were both in the film "Pushing Tin". He later took on roles in films like "Monster's Ball" (2001), "The Man Who Wasn't There" (2001), and "Bad Santa" (2003). In more recent years, he's showcased his talent on the small screen, earning critical acclaim for his role in the series "Goliath". His recent work in the Paramount+ series "Landman" alongside Demi Moore has further solidified his status as a versatile and enduring performer.

Thornton's recent nomination for a Golden Globe in 2025 shows that his ability to deliver compelling performances remains sharp. Its the result of his dedication to the craft that keeps him relevant and respected. His continued success proves that he is not one to be typecast, and his dedication to authenticity continues to resonate with audiences.

He has also made rare comments on his relationships. In a 2008 interview with Maxim, Thornton revealed his intention to possibly stop at five weddings. However, life had other plans. He made rare comments about being married a total of six times, further highlighting the complex nature of his life.

Billy Bob Thornton is known to his fans, not just for his professional life, but also for his personal life. In recent years he has been seen attending the premiere of his new western drama, Landman, alongside his wife, Connie Angland, whom he married in 2014. The pair have been together since 2003. The actor's life continues to evolve.

The details surrounding his life and relationships is a reminder that true charisma is not just about acting ability but also about the willingness to live a life that is unapologetically authentic. He has never been afraid to embrace the unexpected, in both his personal and professional life. From the early days in Arkansas to the bright lights of Hollywood, Billy Bob Thornton remains an intriguing and enigmatic figure, a man who has always chosen his own path.