Val Kilmer Loved 1 Celebrity Girlfriend the Most

Actor Val Kilmer dated many top actresses over the years, including Cher and Angelina Jolie, but his split with one top actress caused him the most pain.

According to People, in his memoir, Kilmer revealed that he was heartbroken when he and actress Daryl Hannah broke up, writing, “Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all."

“I knew I would love her with my whole heart forever and that love has lost none of its strength. I am still in love with Daryl," he also wrote, according to The Sun. “When we broke up, I cried every single day for half a year."

Kilmer, 65, died on April 1 in California of pneumonia after struggling with throat cancer for years, his daughter Mercedes Kilmer told The New York Times. She is the daughter of Kilmer and his only wife, actress Joanne Whalley.

“I’ve always found women infinitely more interesting than men,” Kilmer wrote in his 2020 memoir, I’m Your Huckleberry. according to US Weekly. “Perhaps that’s why we’ve always gotten along. We are big oafy elephants … and they are butterflies.”

According to US Weekly, Kilmer was married to Whalley from 1988 through 1996, and they welcomed son Jack as well as Mercedes. He never married again.

Kilmer dated model Cindy Crawford after breaking up with Whalley, US Weekly reported.

Kilmer dated Cher in the 1980s, and they stayed friends, People reported.

“Once Cher works her way inside your head and heart, she never leaves. For her true friends, her steadfast love and loyalty never die,” he wrote, according to People. The Sun reported that he also dated Carly Simon, but he stopped dating after Hannah.

Of Angelina Jolie, he wrote, according to People, that she was "perhaps the most soulful and serious of them all. When people ask what she’s like, I say she’s like other women and other superstars, just MORE."