Who: Oscar-winning actress, director, and humanitarian Angelina Jolie, 43, and Oscar-winning writer, actor, director, and singer Billy Bob Thornton, 63.

How They Met: Angelina and Billy Bob met on the set of 1999 dramedy Pushing Tin, in which they played husband and wife. Both were romantically attached at the time — he to fiancée Laura Dern, and she (newly separated from husband Johnny Lee Miller) to boyfriend Timothy Hutton.

In May 2000, the former co-stars wed in Las Vegas, shocking the world, and perhaps most of all Dern, who said she “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.”

Why We Loved Them: Between trading vials of blood (which were really more like lockets with just a touch of genetic personalization), branding themselves with giant tattoos of each other’s names, and swapping underwear, Billy Bob and Angelina were the picture of early aughts romantic extremity.

When They Peaked: It really doesn’t get any better than this interview at the premiere of Gone in 60 Seconds in which a trucker hat-clad Thornton, fighting to speak between makeout sessions with Jolie, admits to an MTV reporter that he and his bride “f—ked in the car on the way here.”

The Breakup: Thornton and Jolie called it quits in the summer of 2002, just a little over two months past their two-year anniversary.

At the time, Thornton told reporters, “I don’t think either one of us knows why we split up. It was like, say you’re going to a nightclub one night with your friends and you’re in line and the next thing you know there are guys with helicopters and there’s machine-gun fire and you don’t know what happened. And that’s kind of like what our breakup was like.”

Though a very vivid description, more than a decade later the Sling Blade star said he “never felt good enough for [Jolie].”

He recently expanded upon that comment during an episode of the HFPA in Conversation podcast, explaining, “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.”

Jolie has said much of the same, telling Barbara Walters "[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.”

The Girl, Interrupted star adopted her son Maddox the November prior to her and Thornton’s split.

Where They Are Now: Professionally, Jolie has turned her attention to her humanitarian work and currently serves as a Special Envoy to the United Nations High Commissioner for Refugees. As for her Hollywood endeavors, Angelina stars as the titular lead in Disney’s Maleficent franchise and is attached to Peter Pan and Alice in Wonderland sequel Come Away.

Two years after her divorce from Thornton was finalized, Angelina entered into another tabloid-frenzy of a relationship with none other than Brad Pitt. Pitt soon adopted Maddox (now 17), and the couple went on to welcome five additional children together: Pax, 15, Zahara, 14, Shiloh, 12, and twins Vivienne and Knox, 10. Brangelina announced their separation in 2016 after 11 years together and two years of marriage.

Thornton currently stars in the critically acclaimed Amazon Prime series Goliath, for which he won his second Golden Globe in 2017. It appears he’ll be turning his sights back to directing and writing for an upcoming road movie, And Then We Drove.

The Bad Santa star wed his sixth wife, Connie Angland, in 2014. They share a 14-year-old daughter, Bella, together.