From Daryl Hannah to Angelina Jolie, Val Kilmer’s dating history explored

Hollywood star Val Kilmer has passed away at the age of 65 in Los Angeles, according to a report in The New York Times. Kilmer, whose hits include Top Gun, The Doors, and Batman Forever, died on April 1, 2025,.

The cause of death was pneumonia, as confirmed by his daughter Mercedes Kilmer to the outlet. She added that he was diagnosed with throat cancer in 2014 but later recovered. Kilmer is reportedly survived by his children, Mercedes and Jack, whom he shares with former wife and actress Joanne Whalley. They were reportedly married for eight years, from 1988 till 1996.

However, the actor was reportedly single at the time of his death. According to People, in his 2020 memoir, I'm Your Huckleberry: A Memoir, he revealed that he hasn't had a girlfriend in 20 years.

In addition to a prolific career in the '80s and '90s, Kilmer was known for his high-profile relationships with celebrities such as Cher, Cindy Crawford, Angelina Jolie, and Daryl Hannah. Let us explore his dating history.

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Everything we know about Val Kilmer’s dating history

Val Kilmer had a fascinating dating history, which was marked by relationships with several high-profile women in Hollywood and beyond.

During his teens, Kilmer dated his high school sweetheart, Mare Winningham. In a Facebook post dated November 16, 2018, Kilmer has described her as:

“my first real girlfriend.”

They were members of their school’s drama club alongside Kevin Spacey, reported Remind magazine.

When Kilmer was in his 20s, he found love in Cher, during the 1980s, a report in US Weekly stated. Recalling the early days of their relationship the singer told People magazine in 2021:

“He's like nobody I've ever known. He was so young. Was he 22? What was I? I don't know. Thirty-something. It was a bigger deal back then. The truth was if I hadn't gone out with younger men, I would have never had a date. Younger men weren't intimidated by older women. But older men in my age category, they weren't having it.”

Cher admitted they were madly in love. The actor went on to date Carly Simon and Ellen Barkin, before meeting his future wife, Joanne Whalley. They wed in 1988 after a whirlwind romance, and their marriage ended in a divorce in 1996.

Kilmer went on to date supermodel Cindy Crawford after his divorce. They met for the first time at the premiere of Batman Forever in 1995.

“I thought I could have died from her love because its delight was simply too much to bear,” he wrote in his memoir, according to The Sun.

“Did I date Cindy Crawford? Yeah, she’s very nice. A smart girl with a great sense of humor,” he told The Guardian in 2005, according to Remind magazine. Kilmer claimed that she helped him find happiness after his divorce.

Kilmer dated Daryl Hannah in the early 2000s after they met while working together on the film, In God We Trust. He has described his break-up from Hannah as the most painful of all. A report in People magazine indicated that the actor wrote in his memoir:

“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.).” Kilmer was referring to the fact that Hannah married Young in 2018.

Kilmer then dated Angelina Jolie in 2004. They worked together in the film, Alexander.

“When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more,” he wrote in his book, as reported by US Weekly.

Kilmer continued, about Jolie:

“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.”

After their split, Jolie started dating Brad Pitt, and Kilmer moved on with producer Jaycee Gossett, who were often pictured together on the red carpet.