The Top Gun actor credited his split with the Splash star as his “most painful.” 

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Val Kilmer, Daryl Hannah
Val Kilmer, Daryl Hannah
| Credit: Frank Trapper/Corbis via Getty Images

Who: Splash actress Daryl Hannah, 60, and Top Gun actor Val Kilmer, 61.

How They Met: Given their respective roles in the zeitgeist of the late 20th century, I find it hard to believe that the actors' paths first crossed in the early aughts. And while it's possible that they met earlier, it wasn't until they worked together on Hard Cash (otherwise known as In God We Trust) in 2001 that things turned romantic between them. 

Why We Loved Them: I mean, look at them!

TBT: Val Kilmer and Daryl Hannah
Credit: Jon Kopaloff/FilmMagic

Not for nothing, when asked which ex he'd let dress him for court in the event that he was sent to jail for shoplifting (?), Kilmer named Hannah and commended her style. "Daryl Hannah likes to goof around with fashion," he told Elle, "but she does have pretty impeccable taste."

When They Peaked: 

In Kilmer's 2020 memoir I'm Your Huckleberry, the actor shared a silly anecdote about the time he and Hannah spent at her "exquisitely refurbished barn in Telluride."

"Leaning against a wall was a remarkable piece of art, a long, wide plank of wood," Kilmer wrote. "I saw it as a daring piece of avant-garde sculpture. I had to know the name of the sculptor." 

Hannah laughed and told him it was just her snowboard, made for her by Jake Burton Carpenter (the man behind Burton Snowboards). "He said he'd never made one for a woman," Hannah added. 

TBT: Val Kilmer and Daryl Hannah
Credit: George Pimentel/WireImage

The Breakup: 

Nearly two decades after they split, Kilmer wrote that splitting from Hannah was "by far the most painful" heartache he'd experienced — mind you, his roster of exes includes Cher, Cindy Crawford, and Ellen Barkin. He claimed to have cried every single day for six months following the breakup. 

Kilmer said he would've "done anything to win [Daryl] back," and that he knew he'd "love her with my whole heart forever."  

"That love – invisible, ephemeral, and infinite – has lost none of its strength," he went on. "I am still in love with Daryl." 

Still, he admitted that he "made mistakes" with his ex. "Maybe it was possessiveness. Maybe it was ego."

Though Hannah does not appear to have commented directly on the breakup, she remarked that it hadn't been her "luck to find the right person" in 2005. 

Kilmer also took a stab at Hannah's current husband, Neil Young, writing that while he "always loved" the musician, "I'm afraid I hate you now."

Where They Are Now:

Hannah wed Young in 2018 after several years together. She was previously linked to John F. Kennedy Jr., Jackson Browne, and David Blaine. 

Next up for the actress is miniseries The Now

Kilmer claimed in his 2020 memoir that he hasn't had a girlfriend in 20 years, the last of which was presumably Hannah. 

The actor's self-titled documentary, Val, is out now on Amazon Prime.