When Billy Bob Thornton jokes about living at the Sunset Marquis every time he gets divorced, it’s clear he’s a man who’s learned to find humor in heartbreak. But behind the laughs and the public eccentricity lies a private, deeply shy storyteller who’s been through more than his share of headline-making relationships—and who, for a brief, unforgettable moment, was half of Hollywood’s most bizarre and beloved couple.

A Life of Love, Loss, and Headlines

Billy Bob Thornton has never been your typical Hollywood leading man. He’s been married five times, and each relationship has left its mark on him—sometimes quietly, sometimes in ways that still echo through the tabloids today. “People think that’s some bizarre thing,” he once said. “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.”

His first marriage, to Melissa Lee Gatlin in 1978, brought a daughter, Amanda, but ended in estrangement and tragedy. Amanda grew up apart from Billy Bob and later made headlines of her own, serving prison time before her release in 2020.

Marriage number two, to Toni Lawrence, was brief and left little public trace, but Toni later described Billy Bob as “very talented” and “very troubled.” His third wife, actress Cynda Williams, would later say they were “just friends and should never have been married.” Petra Dawn Cherniak, a Playboy model and his fourth wife, brought two sons into his life but also a contentious split, with allegations of abuse that Billy Bob denied.

Falling for Angelina: Hollywood’s Oddest Match

But it was Billy Bob’s fifth marriage that truly made headlines. On the set of 1999’s Pushing Tin, he fell for Angelina Jolie—even though he was engaged to Laura Dern at the time. Dern later recalled, “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.” Billy Bob, in his own words, said, “I had to follow my heart… I’m sorry it caused pain.”

From 2000 to 2003, Billy Bob and Angelina were the wildest couple in Hollywood—matching tattoos, grave plots, and, most famously, lockets with drops of each other’s blood. “It was just a symbolic thing,” Billy Bob later explained. “It just sounds good to talk about.” In reality, they were tiny lockets, not “buckets of blood” as the media sometimes claimed.

Despite the public oddities, their marriage was, for a time, deeply committed. “We kind of signed our life away to each other—legally and with blood,” Angelina said at the start. But only months after they adopted a child from Cambodia, the couple split. Angelina would go on to adopt Maddox as a single parent.

Why Did It End? The Real Reason Behind the Divorce

So why did this eccentric but passionate marriage unravel? Billy Bob’s answer is surprisingly vulnerable. He admits he never felt good enough for Angelina, who thrived in the global spotlight while he was most comfortable at home, away from crowds. “She was a global traveler. I was almost agoraphobic,” he said. “She wanted to go to big events and talk to everyone. I’d hide in the corner.”

Ultimately, their lifestyles were simply too different. Both needed someone more compatible. Billy Bob’s honesty about his insecurities—and his admiration for Angelina’s ambition—remains one of the most refreshing takes on a Hollywood breakup.

Addressing the Rumors and the Reality

Billy Bob Thornton has always been candid about his quirks, and the media has never lacked for material when covering his life. He’s the first to admit that he and Angelina “had a lot of fun together,” and that some of their antics were “a bit morbid”—like picking out grave plots. But he’s also quick to clarify: “A lot of the stuff we do is really not that big a deal. It just sounds good, you know, to talk about.”

As for those infamous blood lockets? “They’re not actually vials,” he laughs. “Just little lockets, like you put a picture in. We’d poke our finger, put a drop of blood. It was just symbolic.”

Where They Stand Today

Not all of Billy Bob’s divorces ended on good terms, but with Angelina, there’s only respect. “I look at that time as a great time. Angie is still a friend of mine and she is a great person. She’s done so much,” he says. He admires how she’s moved from acting to directing and producing, always following her heart—just as he’s done by focusing on streaming TV and independent projects.

A New Chapter: Finding Peace

Billy Bob once swore off marriage after Angelina, but love found him again. He met Connie Angland on the set of Bad Santa in 2003. After 11 years together, they married in a private ceremony in 2014 and have a daughter, Bella, who is homeschooled. Even GQ Magazine noted Connie is more his speed—a fellow homebody who shares his love of privacy.

Today, Billy Bob seems genuinely happy, spending time with his family and away from the Hollywood circus. He’s found the quiet he always craved, and the peace that eluded him for so long.

The Last Word

Billy Bob Thornton’s romantic journey is a testament to the unpredictability of love, the pain of public scrutiny, and the possibility of redemption. His story with Angelina Jolie was wild, unconventional, and unforgettable—but it ended not with scandal, but with honesty and respect.

Who’s your favorite celebrity couple who eventually parted ways? Let us know in the comments below—and don’t forget to subscribe for more real-life Hollywood stories that go beyond the headlines.