Latest Shocking Entertainment News: Val Kilmer’s Dating History: Cher, Angelina Jolie, Cindy Crawford, More
Val Kilmer was linked to Cindy Crawford, Angelina Jolie, Cher and more celebrities throughout his life.
The Batman Forever star’s daughter, Mercedes Kilmer, confirmed her father died of pneumonia on Tuesday, April 1, per The New York Times.
“I’ve always found women infinitely more interesting than men,” the Top Gun star wrote in his 2020 memoir, I’m Your Huckleberry. “Perhaps that’s why we’ve always gotten along. We are big oafy elephants … and they are butterflies.”
While he was in several public relationships, Kilmer only walked down the aisle once. He married actress Joanne Whalley in 1988. After welcoming daughter Mercedes in 1991 and son Jack in 1995, they called it quits, finalizing their divorce in 1996.
While he moved on from his spouse with Crawford in the ’90s, he referred to his split from Daryl Hannah, whom he dated in the early 2000s, as his “most painful” heartbreak of all.
Kilmer also claimed that he hadn’t “had a girlfriend in 20 years. The truth is I am lonely part of every day.”
The actor died at age 65 in April 2025. His death certificate later confirmed that his cause of death was pneumonia.
Keep scrolling for Kilmer’s complete dating history:
Cher
Kilmer and the musician were linked in the '80s after meeting at Cher’s birthday party. "He's like nobody I've ever known," she told People in 2021, adding that the twosome were "madly in love” during their relationship. "He was so young. Was he 22? What was I? I don't know. Thirty-something. It was a bigger deal back then. The truth was if I hadn't gone out with younger men, I would have never had a date. Younger men weren't intimidated by older women. But older men in my age category, they weren't having it.” In November 2024, Cher revealed on The Howard Stern Show that Kilmer was the only ex to break up with her and it was due to their 13-year age gap. She gushed that she was “madly in love” with the actor. Cher paid tribute to Kilmer after his April 2025 death, writing via X, “Will miss u, U Were Funny, crazy, pain in the ass, GREAT FRIEND, kids💜U, BRILLIANT as Mark Twain, BRAVE here during ur sickness.”
Carly Simon
Kilmer dated the singer after his relationship with Cher, writing in his book, “I wanted to be with Carly every day of the rest of my life.” Their romance didn’t last, however. He reflected on his relationship with Simon via Twitter in 2017, writing, “Once Carly Simon awoke me in her guest bedroom w/bfast and an acoustic guitar- played me a new song she'd just written. I wept. An angel…”
Ellen Barkin
In his book, Kilmer praised the actress, whom he had a “whimsical” romance with in the 80s, for her “wit,” “sultry eyes,” “laugh” — and hair. “Who remembers the softness of a woman’s hair? If you ever have a chance to consensually ever so gently touch Ellen’s hair, it will be worth the look she’s gonna drop on you,” he wrote.
Joanne Whalley
The Willow costars wed in 1988 after a whirlwind romance. The actress filed for divorce shortly after she gave birth to son Jack in 1995. They also share daughter Mercedes.
Cindy Crawford
He was linked to the supermodel after his divorce in 1996. “You have to be committed with a woman that's as dynamic and as committed to their work as someone like Cindy Crawford who was the number one model on the planet at the time,” he told Good Morning America of their romance in 2020.
Jaycee Gossett
He was linked to the producer for two years in the late 90s and early 2000s. “This was my girlfriend Jaycee Gossett and my best friend at the time,” Kilmer wrote alongside a throwback photo via Twitter in 2018. “My favorite Republican #gordonmiller. For some reason I was often invited to the #Whitehouse back then. Not so much now. The White House is a very cool place.”
Daryl Hannah
Following their 2001 romance, Kilmer “cried every single day for half a year,” he wrote in his book.
Angelina Jolie
Kilmer worked with the Oscar winner on the 2004 movie Alexander. “When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more,” he wrote in his book. “More gorgeous. More wise. More tragic. More magic. More grounded. Is it worth it? Worth knowing people who require weeks of effort to understand even a little? Yes.”
Paris Hilton
In 2006, Entertainment Tonight reported photos of the Wonderland costars making out four years prior.
by Sarah Hearon
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