Val KIlmer and Cher at the Academy Awards on April 11, 1983 in Los Angeles, California. ; Val Kilmer and Joanne Whalley attend the “Hurlyburly” Opening Night Party on November 16, 1988 in Century City, California. Photo:

Barry King/WireImage ; Ron Galella, Ltd./Ron Galella Collection via Getty

Val Kilmer, who died at 65 from pneumonia on April 1, was romantically involved with famous figures over the years.

Throughout his prolific career in Hollywood, the actor dated fellow A-listers, including Cher, Cindy Crawford and Angelina Jolie. Most notably, he was married to actress Joanne Whalley for nearly a decade. The couple welcomed two children before they split in 1995.

Years later, Kilmer told The Guardian in a May 2005 interview that he’d “recommend marriage.”

“It’s a lot of security and comfort. It’s naturally how we are; we pair up as a species. Would I get married again? Sure,” he explained.

Fast forward to 2020, Kilmer revealed in his memoir, I’m Your Huckleberry: A Memoir, that he had not had a girlfriend in 20 years.

Still, he admired women for different reasons. “I’ve always found women infinitely more interesting than men,” he wrote. “Perhaps that’s why we’ve always gotten along. We are big oafy elephants … and they are butterflies.”

Here’s a look back at Val Kilmer’s dating history.

Cher and Val Kilmer. Ralph Dominguez/MediaPunch/Alamy

Legendary singer and actress Cher might be better known for her marriages to Sonny Bono and Gregg Allman, but she also dated Kilmer after they met at a birthday party in the early ’80s.

“We became friends because we laughed at the same things constantly. He would sleep over and it was just a friendship [at first],” she told PEOPLE in August 2021.

Eventually, Kilmer and Cher’s connection turned romantic, which evolved into artistic admiration. “It went from madly in love and laughing hysterically to respecting each other’s ability,” she added.

The couple dated for a few years before splitting. “We had unbelievable times and then put up with some times when they weren’t [that way] because we were both Alpha males,” she continued, alluding to why they broke up. “We were both individuals and neither of us was going to give up on that.”

Afterward, Kilmer and Cher stayed friends. In his memoir, the actor wrote about his 2015 throat cancer diagnosis and the support she gave him through his illness. Kilmer stayed in Cher’s guest home while his health was in decline.

“One night I suddenly awoke vomiting blood that covered the bed like a scene out of The Godfather. I prayed immediately, then called 911. Then alerted my hostess,” he said. “Cher stepped in and stepped up.”

More recently, Cher reflected on their relationship during a November 2024 interview with The Howard Stern Show. “Sometimes, you’re only meant to stay with someone so long and Val was … really young,” she said.

Ellen Barkin. ; Val Kilmer. PictureLux / The Hollywood Archive / Alamy ; Michael Ochs Archives/Getty

In the 1980s, Kilmer dated fellow actress Ellen Barkin, who has starred in movies like Switch, Fear and Loathing in Las Vegas and Ocean’s Thirteen.

In his memoir, Kilmer described Barkin, who was born in the Bronx, N.Y., as having “the best smile in all five boroughs.”

The actors were together only briefly, but Kilmer recounted some of his favorite features of her decades later. “I remember her wit, her sultry eyes, but mostly her laugh. And her hair,” he wrote.

Kilmer recalled “window-shopping on Rodeo Drive by day and barbecuing at night” and revealed that Barkin was “one of the enchantresses who got away, no doubt due to my unmanageable preoccupations, my neglect.”

In a November 2006 interview with Elle, he shared that out of his previous partners, if he were arrested, he’d pick Cher as his character witness. Meanwhile, Kilmer quipped that he would “most fear” Barkin to testify against him.

Val Kilmer and Joanne Whalley. Ron Galella, Ltd./Ron Galella Collection/Getty

Kilmer met English actress Joanne Whalley in 1987 while they were filming the movie Willow. They married in 1988 and had two kids: Mercedes was born in 1991 and Jack was born in 1995.

Shortly after welcoming Jack, the couple separated, and Whalley filed for divorce from Kilmer, citing irreconcilable differences.

In 2017, Whalley, Mercedes and Jack joined Kilmer for an interview with The Hollywood Reporter in which he discussed his throat cancer.

Mercedes followed her parents into acting, starring as Kilmer’s on-screen daughter in the 2020 crime thriller film Paydirt. Similarly, Jack has landed roles in several movies, including Palo Alto, Lords of Chaos and The Pretenders.

Cindy Crawford and Val Kilmer. Sacha Orlov/Getty

Supermodel Cindy Crawford first crossed paths with Kilmer at the premiere of Batman Forever in 1995. At the time, he had recently separated from Whalley, and she was divorced from Richard Gere.

Kilmer and Crawford dated for two years, splitting in 1997.

The actor mentioned Crawford in his memoir, expressing his “gratitude” for their relationship.

“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.

In a May 2005 interview with the Guardian, Kilmer described her as “very nice” and “a smart girl with a great sense of humor.” He added, “She’s a fantastic cook, too, always carried recipes around when she traveled.”

Val Kilmer and Jaycee Gossett. Ron Galella, Ltd./Ron Galella Collection/Getty

Kilmer began dating producer Jaycee Gossett in about January 1998.

At the time, New York Magazine reported that the actor had been spending time with Gossett, who had recently turned 20 and worked at a restaurant in New York’s West Village.

In 2018, he posted an Instagram photo in which Gossett was shaking hands with then-president Bill Clinton.

“#TBT This was my girlfriend Jaycee Gossett and my best friend at the time, my favorite Republican #gordonmiller,” Kilmer wrote. “For some reason I was often invited to the #Whitehouse back then. Not so much now. The White House is a very cool place.”

Val Kilmer and Lesley Ann Warren. Ron Galella, Ltd./Ron Galella Collection/Getty

Kilmer briefly dated actress Lesley Ann Warren, who starred in the CBS series Mission: Impossible and NBC’s Harold Robbins’ 79 Park Avenue.

In an interview with Closer Weekly, Warren said that she had only gone on one date with Kilmer. The pair later starred in 10th & Wolf (2006) together.

Val Kilmer and Daryl Hannah. Featureflash Archive / Alamy

Kilmer began dating actress Daryl Hannah after they were costars in In God We Trust in 2001. They broke up the following year, and she later married Neil Young in 2018.

In his memoir, Kilmer recalled the time they spent together in New Mexico and wrote that his breakup from Hannah was particularly painful.

“Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all,” he wrote, jokingly adding, “Neil Young, I always loved you, but I’m afraid I hate you now.”

Val Kilmer and Angelina Jolie. PA Images / Alamy

Actress Angelina Jolie worked with Kilmer on the 2004 film Alexander, in which they played the parents of Alexander the Great.

“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 in his memoir.

He also told director Oliver Stone that he’d only take the part if he and Jolie “could have flashbacks to falling hard for each other and storming the castle with passion, before turning against each other.”

Kilmer described Jolie as “perhaps the most soulful and serious” of the women he’d dated. He continued, “When people ask what she’s like, I say she’s like other women and other superstars, just MORE.”