‘She Never Leaves Your Heart’: A Look Back at Every Woman the Late Val Kilmer Loved
From Cher to Angelina Jolie, these are the women who captured Val Kilmer’s love over the years
Beloved actor Val Kimer died from pneumonia on Tuesday, April 1, 2025. He was 65 and best known for his work in Top Gun (1986) and Batman Forever (1995). To honor him and the legacy he left on the film industry, we have rounded up every woman he loved and found out what he remembered about their time together. Read on for more.
Cher (1982 to 1984)
In the early 1980s, Kilmer dated the legendary singer Cher for two years when he was in his early 20s and she was in her late 30s.
“Once Cher works her way inside your head and heart, she never leaves,” the actor wrote in his 2020 memoir I’m Your Huckleberry. “Cher trafficked an intoxicating glamour and I, a Valley boy, fell under her spell.”
“We had a wild ride, and though we’d eventually veer off in different directions, our spirits stayed united.”
The pair did remain friends until his death in April 2025, with the singer writing on X (formerly known as Twitter), “Will miss u, U Were Funny, crazy, pain in the *ss, GREAT FRIEND.”
Ellen Barkin (1984)
Following his split with Cher, Kilmer dated actress Ellen Barkin, who the actor said has “the best smile in all five boroughs.”
“I remember her wit, her sultry eyes, but mostly her laugh. And her hair,” he continued in his memoir. “[She was] one of the enchantresses who got away, no doubt due to my unmanageable preoccupations, my neglect.”
It is unclear when exactly the pair split, or why they did, but Barkin eventually got married and welcomed a daughter and a son with ex-husband Gabriel Byrne.
Carly Simon (1980s)
Another person Kilmer dated after his split with Cher was singer Carly Simon.
According to the actor, he “wanted to be with Carly every day of the rest of my life,” but the two sadly went their separate ways. The reason why or when it happened remains a mystery.
Simon has been married twice and has two children.
Joanne Whalley (1987 to 1996)
Kilmer’s first and only wife was Joanne Whalley. The two met on the set of Willow in 1987, got married in 1998 and eventually welcomed two kids together in 1991 and 1995.
“Thank you for honoring our extraordinary father’s memory,” Mercedes and Jack Kilmer said in a statement following their father’s death. “We are so proud of him and honored to see his legacy celebrated.”
Kilmer and Whalley eventually divorced in 1996, due to “irreconcilable differences.” Several people believe that this is because of Kilmer’s “sex symbol” status on set, but that has never been confirmed.
Whalley never remarried and is 63 years old.
Cindy Crawford (1995 to 1997)
Kilmer’s first relationship post-Whalley was with beloved supermodel Cindy Crawford, whom he met at the Batman Forever premiere in 1995.
“Oh God, I loved Cindy and just kept loving her,” Kilmer wrote in his memoir. “I thought I could have died from her love because its delight was simply too much to bear. I would die of happiness.”
Eventually, the couple split in 1997 after finding it increasingly more difficult to find time together due to their busy schedules.
Jaycee Gossett (1998)
In January 1998, Kilmer began dating producer Jaycee Gossett when she was 20 years old and he was 38.
Kilmer remained rather tight-lipped about his relationship with Gossett, but in 2018, he did post a picture on Instagram of the two of them with former president Bill Clinton.
‘This was my girlfriend Jaycee Gossett and my best friend at the time, my favorite Republican #gordonmiller,” the caption read. “For some reason, I was often invited to the #Whitehouse back then. Not so much now. The White House is a very cool place.@billclinton.”
Kilmer and Gossett eventually broke up in the early 2000s—the reason why is unknown.
Lesley Ann Warren
At some point, Kilmer dated actress Lesley Ann Warren. It is unclear when, but based on the actor’s other relationships, it was most likely at some point in the early 2000s.
According to her, they went on one date, “so there’s nothing really fabulous to report!” per Closer.
Warren is 78 and has been married to Ron Taft since 2000. She has one child with her ex-husband, Jon Peters.
Daryl Hannah (2001)
Kilmer and Daryl Hannah met on the set of the 2002 film Hard Cash. They dated for about a year before splitting up. Hannah then married rock legend Neil Young in 2018.
“Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all,” Kilmer wrote in his memoir. “Neil Young, I always loved you, but I’m afraid I hate you now.”
Angelina Jolie (2004)
One of Kilmer’s most famous relationships was with Angelina Jolie. They worked together on the 2004 Alexander, where they played Olympias and Philip.
“I couldn’t wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail,” Kilmer 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.”
Following their split, Jolie married Brad Pitt and is currently still dealing with the aftermath of their divorce, specifically regarding custody.
This was the last public relationship Kilmer was ever in.
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