He had relationships with some of Hollywood’s most iconic women, but there was only one who truly broke Val Kilmer’s heart. In his memoir, released shortly before his death, the actor revealed the woman who changed his life — and the pain he carried long after their breakup
Val Kilmer at the “Hurlyburly” opening night party on November 16, 1988, at the Twenty/20 Club in Century City, California. | Source: Getty Images
Once a symbol of Hollywood’s golden age — intense, bold, and unforgettable in roles like Jim Morrison, Doc Holliday, and Batman — Val Kilmer drew just as much attention for his love life as he did for his acting career.
Beneath his high-profile relationships, however, there was one love that stayed with him long after it ended. In his memoir, Kilmer shared the heartbreak that haunted him for decades, a pain so deep that he struggled to move forward, even as the woman he lost found love again.
Val Kilmer at the Simply Shakespeare’s Live Read of “The Merchant Of Venice” at Walt Disney Concert Hall on October 28, 2019, in Los Angeles, California. | Source: Getty Images
The Love That Stayed With Val Kilmer
On April 1, 2025, the entertainment world lost one of its brightest stars when Kilmer passed away at 65 in Los Angeles, following a battle with pneumonia. Though he had been diagnosed with throat cancer in 2014, he made a remarkable recovery and continued to work, while openly discussing his health struggles.
Mickey Rourke, Daryl Hannah, and Val Kilmer at the premiere “Masked and Anonymous” during the 2003 Sundance Film Festival on January 22. | Source: Getty Images
Throughout his life, Kilmer’s love life attracted just as much media attention as his films, with many women by his side over the years.
But the one that affected him most was actress Daryl Hannah. Hannah, known for roles like the mermaid Madison in Splash, Pris in Blade Runner, and Elle Driver in Kill Bill, became an important part of his life in 2001 after they worked together on In God We Trust. Their bond quickly turned into something far more meaningful than a fleeting Hollywood romance.
Daryl Hannah and Val Kilmer during the “Wonderland” premiere on September 24, 2003, in Hollywood, California. | Source: Getty Images
In his memoir I’m Your Huckleberry, Kilmer looked back on their relationship with a mix of reverence and sorrow, writing:
“I would love her with my whole heart forever. That love — invisible, ephemeral, and infinite — has lost none of its strength. I made mistakes with Daryl. Maybe it was possessiveness. Maybe it was ego.”
Kilmer admitted that their breakup left a permanent scar. “But Daryl was by far the most painful of all. Suffice it to say, I would have done anything to win her back. God’s perfect plan of peace sometimes cannot be understood yet must be followed,” he wrote.
Daryl Hannah at the First Annual Environmental Media Awards at Sony Pictures Studios in Culver City, California, on September 30, 1991. | Source: Getty Images
Kilmer’s memoir detailed the emotional impact of their time together, saying, “Losing Daryl felt like the end of that whole piece of my personality. We loved deeply and fought deeply, and every day with her was that unique once-a-decade spring when there’s a beautiful storm followed by a priceless rainbow […].”
He also revealed how the aftermath of their breakup consumed him, admitting:
“I cried every single day for half a year at least, until I became very concerned about my kids seeing me that way. I thought, Grow up. I couldn’t do it anymore, and I couldn’t do it to them.”
Daryl Hannah at the 65th Grammy Awards on February 5, 2023, in Los Angeles, California. | Source: Getty Images
Though years passed, Hannah remained a constant in his memories. He recalled with fondness a particular moment, writing: “I don’t want to stop talking about Daryl. I want to remember the morning we awoke in her exquisitely refurbished barn in Telluride.”
Meanwhile, Hannah eventually moved on and started a life with Canadian rock musician Neil Young. They connected in 2014, bonding over their shared commitment to environmental causes, and later married in a private ceremony on Young’s boat.
Kilmer, on the other hand, reflected on his broader thoughts about love and his own experiences, sharing, “I am a slave to Love. I am a hopeless romantic. I haven’t had a girlfriend in twenty years.” For him, women embodied the emotional depth he valued. He wrote, “The leading qualities of Love, empathy, compassion can be more easily found in a woman than a man or a feminine makeup than masculine. I’ve always found women infinitely more interesting than men.”
Kilmer’s memoir also revealed that, despite his many relationships over the years, he had not had a girlfriend in 20 years.
Daryl Hannah and Neil Young spotted going for a romantic walk in Rome, Italy, on June 27, 2015. | Source: Getty Images
Val Kilmer and Cher at the 56th Academy Awards on April 9, 1984. | Source: Getty Images
As for Hannah, she built a life with Neil Young, a relationship marked by shared activism and an eventual private wedding aboard Young’s boat. Their connection was deep, with Young expressing profound gratitude for their partnership during a press tour.
Val Kilmer and Joanne Whalley at the screening of the CBS Miniseries “Scarlett” on November 3, 1994, in New York. | Source: Getty Images
Cindy Crawford and Val Kilmer photographed on the streets of Moscow, Russia, on April 13, 1996. | Source: Getty Images
A History of Iconic Relationships
Jaycee Gossett and Val Kilmer at the “At First Sight” premiere on January 12, 1999, at the Mann Bruin Theatre in Westwood, California. | Source: Getty Images
While one love remained central to his heart, Kilmer’s romantic history also included several high-profile names. In the 1980s, he briefly dated music legend Cher, after meeting her at her birthday party. He also had relationships with singer Carly Simon and supermodel Cindy Crawford.
Val Kilmer and Angelina Jolie at the premiere of “Alexander” at the Savoy Cinema on January 6, 2005, in Dublin, Ireland. | Source: Getty Images
He married actress Joanne Whalley in 1988, and the couple had two children before their divorce in 1996. Kilmer later had notable relationships with actress Ellen Barkin, Paris Hilton, and producer Jaycee Gossett.
Val Kilmer and Paris Hilton during the “Wonderland” premiere afterparty on September 24, 2003, in Hollywood, California. | Source: Getty Images
In 2004, rumors swirled around his relationship with Angelina Jolie while they worked together on Alexander. But through all the years and relationships, it was the love with Daryl Hannah that left the deepest mark. Despite everything that came and went, Val Kilmer never truly stopped mourning her — a loss he carried with him until the very end.
