Yahoo Lifestyle From Cher to Angelina Jolie—Looking Back at All the A-List Stars Val Kilmer Dated
Val Kilmer, who died Tuesday, April 1, of pneumonia, was known for some iconic roles, ranging from Batman and Jim Morrison to Tom Cruise’s wingman in Top Gun.
Yet he was almost as well known for the women he dated during his prime in the 1980s through 2000. At the time of his death, Kilmer was not in a relationship and hadn’t had a girlfriend for more than 20 years.
He detailed his dating life in his 2020 memoir I’m Your Huckleberry, calling himself a “hopeless romantic” and revealing secrets about his relationships with Cindy Crawford, Carly Simon, Angelina Jolie, Michelle Pfeiffer, Cher and Daryl Hannah.
“I’ve always found women infinitely more interesting than men,” Kilmer wrote. “Perhaps that’s why we’ve always gotten along. We are big oafy elephants…and they are butterflies.”
Carly Simon
Kilmer said he was “hopelessly in love” with the “Nobody Does It Better” singer. He met her at a party for the New York premiere of Top Gun in 1986 that he attended with Cher.
A week later, he visited her home in New York City. “We talked about shyness. We talked about Harry Nilsson. We talked about Bob Dylan and the evils of yellow journalism and the exquisite phrasing of Frank Sinatra. We talked and talked and talked. We had dinner,” he wrote.
Kilmer fell hard for Simon. “I wanted to be with Carly every day of the rest of my life…. She had utter power over me… Our friendship flowered,” he wrote.
“I think the reason we soon stopped seeing each other was her realization that it was too overwhelming for me,” he added. “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.”
Angelina Jolie
The pair met working on the 2004 film Alexander. He wrote that he “couldn’t wait to kiss” her and “buy her a Gulfstream jet and have V+J painted in rainbow glory on the trail.”
As Kilmer wrote in his book, at first, they were friends.
“I was around when Angie's mom [Marcheline Bertrand] was losing her battle with cancer. They were living in her mom's favorite hotel. Or maybe it was Angie's. I happened to be staying there myself. It was meaningful and mortal and effortless and exquisite.”
He went onto to detail their relationship and heap praise on Jolie. “I was recused 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.”
However, the relationship ended after Jolie met Brad Pitt, while working on the 2005 film Mr. & Mrs. Smith.
Daryl Hannah
The Splash actress was Kilmer’s biggest heartbreak, although they dated only briefly in 2001.
“Lord knows I’ve suffered heartache. But Daryl was by far the most painful,” he wrote, adding that he cried every day for six months following their breakup.
“I know I would love her with my whole heart forever and that love has lost none of its strength. I am still in love with Daryl.”
Initially, Kilmer had no interest in dating the iconic singer-actress.
“I saw Cher as a less-than-fascinating character out of the gossip rags,” he wrote. “I was not motivated to meet her, not out of snobbery but simply because I was sure we had nothing in common.”
Yet eventually they did meet, and he ended up taking the “Believe” singer home that night on his Harley.
“We both loved laughing and went on doing so for well over a year,” he wrote. “Funniest woman I ever met.”
Cher revealed during a 2024 interview with Howard Stern that Kilmer broke her heart.
When Stern asked the singer, “Who would ever leave you?”
“Few men. A couple. I was madly in love with Val Kilmer and he left,” she told the radio host.
When Stern pressed her further, she revealed that their age gap was a problem. She was 36 and he was 23 when they dated from 1982 to 1984.
But they remained friends, and she helped care for him when in 2015 when he was diagnosed with throat cancer. Kilmer wrote that he was living in her guesthouse when he started “vomiting blood that covered the bed like a scene out of The Godfather. She called 911 and stayed with him and he had a tracheotomy and was treated with chemotherapy.
“We laughed out loud before they finished my vitals and shut me up with an oxygen mask,” Kilmer wrote.
On Wednesday, April 2, Cher paid tribute to Kilmer, posting on X, formerly Twitter, “VALUS Will miss u,U Were Funny,crazy,pain in the ass,GREAT FRIEND,kids. U, BRILLIANT as Mark Twain, BRAVE here during ur sickness.”
Michelle Pfeiffer
Kilmer met the actress on the set of the 1985 ABC Afterschool Special One Too Many and they struck up a friendship.
He had just split with Cher, and shared information about his parents with her, while Pfeiffer was having marital problems with Peter Horton, who she would eventually divorce.
“The secret pain that Michelle and I shared created an intimacy between us,” Kilmer wrote.
Ellen Barkin
Another older woman Kilmer dated was actress Ellen Barkin, who was six years older than the Top Gun star.
In his book he wrote the Emmy-winning actress had “the best smile in all five boroughs” and added, “I remember her wit, her sultry eyes, but mostly her laugh.”
He also had a thing for 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,” Kimer wrote.
Joanne Whalley
Walley, who Kilmer was married to from 1988 through 1996, is the only woman he ever married. They had two children—Mercedes, 33, and Jack, 29.
They met on the set of the 1988 film Willow and later moved to New Mexico where they married before enjoying a honeymoon on a Tahitian island owned by Marlon Brando.
However, the relationship didn’t last. They divorced in 1995, just two months after the birth of their second child.
Cindy Crawford
Following his Kilmer divorce from Whalley, Kilmer eventually hooked up with Cindy Crawford, who he dated for two years and once said he “could have died” from her love.
“Did I date Cindy Crawford? Yeah, she's very nice. A smart girl with a great sense of humour,” Kilmer said in a 2005 interview with The Guardian. “She's a fantastic cook, too, always carried recipes around when she travelled,” he added.
He talked more about their romance in a 2020 interview with Good Morning America. “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.”
