Val Kilmer dated some of the most famous women in Hollywood.
From Cher Cindy Crawford Angelina Jolie and Daryl Hannah, the late actor – who died aged 65 in April 2025 – had his share of high-profile romances.
However, in his 2020 memoir, Kilmer said he hadn’t had a significant relationship in the two decades leading to the book’s release.
“I haven’t had a girlfriend in 20 years. The truth is I am lonely part of every day,” he wrote in I’m Your Huckleberry.
Here are some of the famous women who became the great loves of the Top Gun star’s life.
Cher
Kilmer dated Cher in the early ’80s after they were introduced at her birthday party.
They would go on to date from 1982 to 1984, with Cher – who was 14 years his senior – having fond memories of their two years together.
“We became friends because we laughed at the same things constantly,” Cher told People.
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“He would sleep over and it was just a friendship [at first.] That took a long time. Well, I guess not really a long time.”
Ultimately, the couple split because they were just two powerful individuals, she said.
“We had unbelievable times and then put up with some times when they weren’t [that way] because we were both Alpha males,” she told the publication.
“We were both individuals, and neither of us was going to give up on that.”
And that quest for independence did get in their way. “What we would put up with from one another, was more than I think I’ve ever had with any other guy,” Cher added.
“He would just go off and do his own thing, and you just had to be prepared. … It went from madly in love and laughing hysterically to respecting each other’s ability.”
Still, the exes remained friends over the years. When Kilmer was diagnosed with throat cancer and underwent a tracheotomy in 2014, it was Cher who helped him through and invited him to stay at her guest house during his health crisis.
“One night I suddenly awoke vomiting blood that covered the bed like a scene out of The Godfather,” he wrote in his memoir.
“I prayed immediately, then called 911. Then alerted my hostess. Cher stepped in and stepped up.”
Kilmer said although it was a terrifying ordeal, Cher managed to find a way to make him laugh by eyeing up the paramedic, who was “drop-dead” handsome.
“Only in Hollywood, right? Despite the fact that I was covered in blood, I caught her eye and bounced my brows like Groucho Marx. Hubba hubba. Cher was bashful to be busted but then couldn’t help laughing out loud at the audacity,” Kilmer wrote.
In his memoir, Kilmer said he would always have a soft spot for Cher – and vice versa.
“Once Cher works her way inside your head and heart, she never leaves,” he wrote.
“For her true friends, her steadfast love and loyalty never die.”
Iconic Hollywood couples from the ’80s
Joanne Whalley
After meeting on the set of the 1988 action-adventure Willow, Kilmer and British actress Joanne Whalley married that same year.
They tied the knot in New Mexico and honeymooned on actor Marlon Brando’s island in Tahiti.
The couple would welcome two children: Mercedes, 30, and son Jack, 26, who both followed in their parents’ footsteps and are now actors.
Sadly, the marriage did not last and they went their separate ways after eight years. The split was messy with the couple reportedly battling for custody and money amid their split. They were officially divorced in 1998.
“My children should not have to live in borrowed homes or hotels,” Whalley, now 60, reportedly claimed at the time.
“Val is such a big superstar now; his family has become superfluous. We’ve become a millstone around his neck.”
Although it’s believed the exes stopped speaking, Kilmer was extremely close to his children.
Cindy Crawford
Kilmer reportedly dated Cindy Crawford, now 56, after the breakdown of his marriage to Whalley. The actor first met the supermodel at the premiere of Batman Forever in 1995.
“Oh God, I loved Cindy and just kept loving her, I thought I could have died from her love because its delight was simply too much to bear. I would die of happiness” he gushed in his memoir.
The couple would go on to date for two years, eventually splitting in 1997.
In a 2005 interview with The Guardian, Kilmer reflected on their romance fondly: “Did I date Cindy Crawford? Yeah, she’s very nice. A smart girl with a great sense of humour. She’s a fantastic cook, too, always carried recipes around when she travelled.”
Angelina Jolie
Kilmer and Angelina Jolie were romantically linked in 2004, when they worked together in the period drama Alexander – just before she met Brad Pitt.
“I couldn’t wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail,” he wrote in his book.
“She had recently adopted her first child, Maddox, and the paparazzi were obsessed with this postmodern Madonna, the perfect picture of unapproachable stardom and impossibly chic maternal instinct.”
The actor said that Jolie “rescued” him from himself and he is forever grateful.
“I was rescued from an icy inferno of solitude by another angel. Perhaps the most soulful and serious of them all. Angelina,” he wrote.
“When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more.”
“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.”
Iconic throwback photos of celebrity weddings
Daryl Hannah
Of all his relationship breakdowns, Kilmer said his split from actress Daryl Hannah was the toughest.
The couple dated in 2001 after working together on the drama In God We Trust.
They were together only for a brief period before splitting, but it seems Hannah was the one who got away.
The actress went on to marry singer Neil Young in 2018 after four years of dating – a union that disappointed Kilmer.
“Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all,” he wrote in his book, before shading her husband in a second remark.
“(Neil Young, I always loved you, but I’m afraid I hate you now.).”
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