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Val Kilmer admitted that one Hollywood breakup left him ‘crying every day’ for half a year
Val Kilmer had many Hollywood romances, but Daryl Hannah was the one that broke him. He admitted crying over the breakup for months.

Actor Val Kilmer had his fair share of Hollywood romances, dating celebrities such as Cindy Crawford, Angelina Jolie, and Cher. But out of all of them, the one that really shattered him was his breakup with Daryl Hannah. In his memoir I’m Your Huckleberry, Kilmer called their breakup the most painful experience of his love life. “Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all,” he admitted.
Kilmer passed away on Tuesday in Los Angeles at 65. According to his daughter, he suffered complications from pneumonia. The Batman Forever star had battled health issues for years, and according to Page Six, he had been bedridden for weeks before his death. His struggle with throat cancer first became public in 2014, and though he recovered, multiple tracheotomies left him with a weakened voice, to the point he was forced to step away from acting for a while. But in 2022, he made a powerful return, reuniting with Tom Cruise in Top Gun: Maverick.
Also read: The Third Edit: Val Kilmer, the Iceman
Kilmer and Hannah started dating after they first met on the set of God We Trust in 2001. However, their relationship came to an end the very next year. Hannah went on with her life and eventually got married. When she married musician Neil Young in 2018, Kilmer couldn’t hide his emotions. In a bittersweet remark, he said, “Neil Young, I always loved you, but I’m afraid I hate you now.” Kilmer also admitted that his love for Hannah never faded. “I knew I would love her with my whole heart forever, and that love has lost none of its strength,” he wrote. Interestingly, when people talk about Kilmer’s long dating history, Hannah is usually just a brief mention. No one expected her to be the one he would say he loved the most. He even confessed that after their breakup, he cried every single day for six months.
Also read: Val Kilmer, star of Batman and Top Gun, dies at 65 after battling cancer
Val Kilmer’s dating history
Before Hannah, Kilmer had the Tinsel town buzzing with his high-profile romance with Cher in the 1980s. The two were a magnet for paparazzi. It is believed that even after their romance fizzled out, she never really left his life—especially when he needed her the most. “Once Cher works her way inside your head and heart, she never leaves,” Kilmer once said. “For her true friends, her steadfast love and loyalty never die.” She was right there when he battled throat cancer, standing by him through the toughest fight of his life.
Kilmer then met British actor Joanne Whalley while filming Willow in 1987. They got married a year later and welcomed two children. But just months after Jack’s birth, their marriage ended, with Whalley citing irreconcilable differences. Kilmer met supermodel Cindy Crawford at the Batman Forever premiere in 1995. They dated for two years before parting ways in 1997. But, according to Kilmer, she left a lasting impression on him. “Oh God, I loved Cindy and just kept loving her,” he wrote in his memoir. “I thought I could have died from her love because its delight was simply too much to bear.”
In the ‘80s, Kilmer briefly dated Ocean’s Thirteen star Ellen Barkin. While working on Alexander (2004), Kilmer played Angelina Jolie’s husband, but he wanted their on-screen love to feel real. “I couldn’t wait to kiss Angie,” he admitted in his memoir. Of all the women he dated, Kilmer said Jolie was “perhaps the most soulful and serious.” Despite his many relationships, Kilmer never settled down again after his divorce. But he never lost his admiration for women. “I’ve always found women infinitely more interesting than men,” he once said.
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