Who: Oscar-nominated and Emmy-winning actress Laura Dern, 52, and Oscar-winning actor Billy Bob Thornton, 64.
How They Met: The actors crossed paths in early 1997 when they both guest-starred on one of the most impactful television episodes in modern history: “The Puppy Episode” of Ellen — i.e. the one where Ellen DeGeneres comes out as gay to Dern, Oprah, and the entire media-consuming world.
At the time, Dern had recently split from Jurassic Park co-star Jeff Goldblum, and Thornton was in the throes of a messy divorce from his fourth wife, model Pietra Dawn Cherniak.
Why We Loved Them: Dern was ever the supportive girlfriend. In late 1998 Thornton admitted he’d gotten unhealthily skinny for a role, telling the Los Angeles Daily News, “Frankly, for a while there, I think I had a little mental problem.” But it was Dern who tried to force him to confront his issue. “I denied it to my girlfriend [Laura Dern] and everyone else who said I had an eating disorder."
Plus, even though Thornton had an unfortunate penchant for the red carpet baseball cap, he and Dern still made a stylish pair.
The Breakup: Oh, boy.
Dern was justifiably shook by this split — or, well, lack thereof? The David Lynch favorite broke her silence on the 1999 breakup (which happened to coincide with Thornton’s surprise marriage to wife no. 5, Angelina Jolie) in 2000, telling Talk magazine, “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.” She then added, “It’s like a sudden death. For no one has there been any closure or clarity.”
Thornton was apologetic (sort of). He weighed in on the controversy in 2001, telling The Guardian, “Others may say that you left our girl and married someone else. But it made me happy and somebody else happy. I'm sorry it caused pain.”
Adding a layer of WTF to the already mottled situation, Dern apparently used to babysit Jolie.
While speaking with Andy Cohen on his Sirius XM radio show in 2016, Melissa Etheridge recounted the situation. “I was around when Angelina was not doing nice things with Billy Bob to Laura Dern,” she shared. “I helped Laura move out of her house with Billy Bob – I like broke into their home to get their stuff out because it was so nasty.”
After 17 years apart, it seems the ice has yet to thaw between the exes. Twitter was sent into a frenzy during the Golden Globes in 2017 when Thornton walked past Dern to accept his award at the podium.
Where They Are Now: Dern went on to marry musician Ben Harper, with whom she shares two children (Ellery, 18, and Jaya, 14). Dern and Harper have since divorced and the Big Little Lies star was most recently linked to former NBA star Baron Davis (and not Bradley Cooper).
The actress can be seen next in Noah Baumbach’s Marriage Story and Greta Gerwig’s Little Women, both out this December. It was recently announced that Dern would reprise her Jurassic Park role in Jurassic World 3.
VIDEO: Laura Dern Just Responded to Rumors That She’s Dating Bradley Cooper
After calling things off with Jolie in 2002, Thornton put the celebrity dating game behind him. “I found celebrity to be difficult just because of privacy issues,” he said in 2017 in reference to his A-list relationships. In 2004 Thornton welcomed daughter Bella with puppeteer Connie Angland, whom he wed in 2014.
Thornton’s Amazon Prime series Goliath returns to the platform for season 3 on Friday, Oct. 4.