Val Kilmer dated Cher, Cindy Crawford, Angelina Jolie and more before going 20 years without a girlfriend
Val Kilmer had a dating history that includes some of Hollywood’s most beautiful and famous women.
However, the "Batman Forever" star, who died this week at 65 years old, revealed five years ago that he had remained single for the last two decades.
In his 2020 memoir, "I’m Your Huckleberry," the "Top Gun" star revealed: "I haven’t had a girlfriend in 20 years," adding, "The truth is I am lonely part of every day," according to People magazine.
Here's a look back Kilmer's A-list dating history before he became single.
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Kilmer and Cher, 78, dated in the early 1980s after the former couple met at a birthday party, she previously told People.
On Wednesday, the "Believe" singer posted a tribute to Kilmer on her social media, calling him "brave," "funny," "brilliant," a "great friend" and a "pain in the a--."
Cher called Kilmer "Valus" in the post, a nickname she had for him when they dated.
She told People in 2021: "Val didn't want to yell ‘Cher’ and I didn't want to yell ‘Val.’ We also called ourselves Valus Maximus and Cherus Reprimandus. It was just kind of who I was in the household. Of course he was Maximus, come on."
She added, "He's like nobody I've ever known. He is exasperating and hysterical. Thrilling and funny and doesn't do what anyone else does."
"It went from madly in love and laughing hysterically to respecting each other's ability," she added of their relationship. "I don't know how we stayed friends, we just did. We didn't try. We just were."
Kilmer wrote in his memoir that after his throat cancer diagnosis in 2015, Cher invited him to stay in her guesthouse.
He said he woke up one night coughing up blood and had to call 911.
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"Cher stepped in and stepped up," he wrote, according to People, adding that Cher even made him laugh because he caught her checking out the paramedic who arrived.
"And yet even in my grave condition, I saw her scanning the paramedic, who was Gregory Peck drop-dead handsome," he wrote. "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 met singer Carly Simon at a party for the premiere of "Top Gun" that he attended with Cher in 1986, Parade reported.
He wrote in his memoir that he fell "hopelessly in love" with the "You’re So Vain" singer, 81, who had an "utter power over" him.
"I wanted to be with Carly every day of the rest of my life," he wrote. He said they eventually broke up because she realized "it was too overwhelming for me. Her shy sensitivity saw through my soul. She saw that I was madly, hopelessly in love with her. I'm not sure I ever spoke those words, but you must have known, Carly."
Kilmer also dated "Animal Kingdom" star Ellen Barkin in the late 1980s.
"I remember her wit, her sultry eyes, but mostly her laugh," Kilmer wrote of Barkin in his memoir, according to the New York Post. "And her 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 called her "one of the enchantresses who got away, no doubt due to my unmanageable preoccupations, my neglect."
Kilmer married English actress Joanne Whalley in 1988 after meeting her on the set of the Ron Howard-George Lucas collaboration "Willow" in 1987.
The former couple had two children: Mercedes, 33, and Jack, 29.
Kilmer told Elle in 2006 that he found out Whalley had filed for divorce in 1995 on TV.
"I was visiting Marlon Brando in Ireland, and I turned on CNN and found out my wife had filed for divorce," he told the magazine. "She took the kids and moved to a different state."
He continued, "You just don't understand humility until you have children and get divorced. I was very hurt and very angry and so was she. But when kids are involved, you either become friends with respect or you become mortal enemies."
When asked about his philosophy on dating co-stars he said: "Never do it."
Kilmer and Whalley were married for eight years, and he never took the plunge again.
Soon after his divorce from Whalley, a young Cindy Crawford came into Kilmer’s life.
The former couple, both fresh off divorces – hers from Richard Gere – met at the 1995 premiere of "Batman Forever."
In his memoir, he wrote that Crawford, 59, helped him get through his divorce, according to Entertainment Tonight.
"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 wrote, People reported.
Kilmer met actress Daryl Hannah, 64, on the set of 2001’s "In God We Trust."
"Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all," he wrote in his memoir, according to People.
He joked of Neil Young, who married the "Splash" star in 2018: "I always loved you, but I’m afraid I hate you now."
He added that after their breakup he "cried every single day for half a year," according to US Weekly.
Kilmer moved on from his heartbreak with Hannah by once again starting a romance with a co-star.
The "Tombstone" star met Angelina Jolie while they were playing the parents of Alexander the Great in 2004’s "Alexander."
"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, according to People.
He added, "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."
Jolie famously moved on with Brad Pitt in 2005 after her breakup with Kilmer.
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After beating throat cancer years before, Kilmer died on Tuesday of pneumonia, the Associated Press reported.