When Val Kilmer Dated Cher, Angelina Jolie, Cindy Crawford, and Many Others

Over the years, 1990s Hollywood icon Val Kilmer hasn’t just been famous for his impressive filmography, which includes everything from Top Gun to Tombstone to Batman Forever — he’s also been famous for a prolific love life that involved his fellow celebrities, including Angelina Jolie, Cindy Crawford, Cher, and more. In fact, Kilmer dated so many famous women, it’s almost a surprise he found the time to act, too.
Read on for a peek into the many women who loved and lost Val Kilmer.
Mare Winningham

Columbia/courtesy Everett Collection
As a teenager in 1970s suburban Los Angeles, young Kilmer found love with future Academy Award nominee and St. Elmo’s Fire star Mare Winningham. Kilmer described Winningham as “my first real girlfriend.” Though they split before either began to tackle Hollywood, there were hints about their future career paths: both were members of their school’s drama club — alongside fellow classmate Kevin Spacey.
The pair reunited on screen in 1985, when they starred in the ABC Afterschool Special “One Too Many” together, alongside a pre-fame Michelle Pfeiffer.
Cher

©TriStar/courtesy Everett Collection
Cher and Kilmer dated for two years, from 1982-84; Kilmer left acting school to join the singer in Las Vegas, where she was staying at Caesar’s Palace. “Cher trafficked in intoxicating glamour and I, a Valley boy, fell under her spell,” Kilmer wrote.
The pairing made headlines because Cher was 13 years older than Kilmer, who made his first film, 1984’s Top Secret, while they were together. Cher recently recalled on the Howard Stern Show that Kilmer, who she was “madly in love with,” was one of the only celebrities to ever break up with her. A year after the breakup, Cher met another Top Gun actor at Madonna and Sean Penn’s wedding: Tom Cruise. The two began to date, and had an even bigger age gap, as he was 23 and she was 38.
Cher and Kilmer have remained friends over the years. When Kilmer was diagnosed with throat cancer and underwent treatment in 2014, Cher who helped him through it, even inviting him to stay at her guest house during his recovery.
Ellen Barkin

Everett Collection
Kilmer dated the Emmy-winning beauty in the ’80s; in his memoir, he remembered their love as “as whimsical as it was whirlwind.” “I was crazy for her, and we had some fabulous days,” he recalled, but the pair broke up, he wrote, “no doubt due to my unmanageable preoccupations, my neglect.”
Joanne Whalley

Everett Collection
After meeting on the set of the 1985 action-fantasy film Willow, Kilmer married actress Joanne Whalley. They had two children together, Mercedes and Jack, before splitting up in 1996. Both children have followed their parents’ footsteps into Hollywood (Mercedes and her dad recently played a father and daughter duo in 2020’s Paydirt), and Kilmer has a great relationship with both.

© Uncorkd Entertainment / Courtesy Everett Collection
During his struggle with throat cancer, Mercedes told People Magazine that the experience brought them closer together. “We all spend so much time together. Even just getting to meet all my dad’s friends from before I was born — there are so many beautiful things that happen when you need help from people.”
Cindy Crawford
Sometime during the mid-1990s, Kilmer paired up with model Cindy Crawford for two years; Kilmer credits Crawford with helping him find happiness after his divorce. “Did I date Cindy Crawford? Yeah, she’s very nice. A smart girl with a great sense of humor,” he said in a 2005 interview with The Guardian. “She’s a fantastic cook, too, always carried recipes around when she travelled.”
Daryl Hannah

©Universal Pictures/courtesy Everett Collection
In the early 2000s, Kilmer dated Daryl Hannah after they met working together on the film In God We Trust. He called their breakup his “most painful” heartbreak.
She would later go on to marry Neil Young in 2018. In his 2020 memoir, I’m Your Huckleberry, Kilmer wrote that the split was devastating for him. “Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all. (Neil Young, I always loved you, but I’m afraid I hate you now.),” wrote Kilmer. “I knew I would love her with my whole heart forever and that love has lost none of its strength.”
Angelina Jolie

Warner Brothers/courtesy Everett Collection
At some point between Brad Pitt and Billy Bob Thornton, Angelina Jolie dated Kilmer. He wrote that Jolie was “perhaps the most soulful and serious of them all. When people ask what she’s like, I say she’s like other women and other superstars, 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.”
The actor recalled working with the actress on the 2004 film Alexander in his memoir. “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. “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.”
Kilmer told director Oliver Stone he would only accept the role of Philip II of Macedonia if his and Jolie’s characters “could have flashbacks to falling hard for each other and storming the castle with passion, before turning against each other.”
“I was half kidding,” he added. “He didn’t pick up on the humor.”
And what about now?
Kilmer has never remarried after his breakup up with Joanne Whalley, and has not been seen in public with a partner in quite some time. “I haven’t had a girlfriend in 20 years,” Kilmer wrote in his memoir. “The truth is I am lonely part of every day.”

TV Weddings
February 2023
This issue brings you the jitters and joys of the most beloved betrothals in TV and movie history.
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