Why Billy Bob Thornton's Brutal Admissions About Failed Angelina Jolie Marriage Have Left Her Heartbroken 'All Over Again'

Angelina Jolie has been left shaken by Billy Bob Thornton's rare reflections on their short-lived marriage, with sources telling OK! the comments reopened old wounds and underscored how different her life looks now, decades after a relationship that once promised everything.

The renewed attention follows an interview Thornton, 70, gave in which he revisited his marriage to Jolie, now 50, who he wed in Las Vegas in 2000 before they divorced three years later. The pair met on the set of Pushing Tin in 1999, adopted son Maddox together in 2002, and became one of the most scrutinized celebrity couples of their era.

Thornton described the split as amicable and rooted in incompatibility.

"That was the one that ended up being a really civilized breakup," he said. "We simply split up because our lifestyles were so different."

He added he and Jolie "had a great time together" and called the relationship "one of the greatest times of my life."

Of their current bond, he said: "She and I are still very, very close friends."

While the comments were measured, people close to Jolie say their impact was anything but neutral.

One source said: "Hearing him frame it as the happiest chapter dredged up everything that might have been for Angie. It landed hard because it highlighted how alone she is now compared with that period of her life."

Another added: "It was traumatic in a quiet way to hear he had spoken in this way about their relationship. It forced her to revisit a time when she felt chosen and adored, which is not how she experiences her personal life today."

Thornton has long spoken candidly about his insecurities during his marriage to Jolie.

In a 2016 interview, he said he "never felt good enough for" the actress, adding: "I'm real uncomfortable around rich and important people."

In a separate chat, he admitted: "I blew it because I didn't think I was good enough for her. She has one way she wanted to live her life and I had another way to live mine and I was just too insecure."

Thornton continued: "I did feel like the Phantom of the Opera hiding in the catacombs. People have actually said that I didn't deserve to be with her."

Those reflections, sources say, cut deeper now. "The way he talks about insecurity and destiny makes it feel like unfinished business," one friend of Jolie's said. "It reframes the breakup as something tragic rather than simply mutual, and that is painful."

Thornton also addressed the intense media scrutiny they faced when married.

"When we got together… for some reason, the people and the media were very interested in celebrity couples. So it was weird," he said.

He also revisited the pair's infamous blood-necklace story, insisting it was exaggerated.

"We each had a little locket, literally with a drop of blood in them. That's a romantic little idea, and that's all that was," he shared.

He added about how the narrative around the necklaces spiraled: "By the time it's over, we're vampires. We live in a dungeon, we drink each other's blood, that kind of stuff."

Since his divorce from Jolie, Thornton has married Connie Angland, 61, and insists he remains on friendly terms with Jolie.

"We're good friends," he said in 2019. "We keep up with each other."

Jolie, who went on to a long marriage and subsequent split from Brad Pitt, has also spoken warmly of Thornton.

"I still love him dearly and think the world of him," she said in 2008. "And I'm proud to have been his wife for a time."

Yet sources say timing matters. One insider added: "Angelina is in a phase of looking inward and taking stock of her life, and hearing him speak so openly about their marriage hit at a vulnerable moment. It revived the emotional weight and intensity of that relationship and reopened feelings she believed she had long since put to rest, leaving her shaken and deeply saddened all over again."