Val Kilmer Details Romances With Angelina Jolie, Cher, Cindy Crawford & ‘Most Painful’ Heartbreak In New Book

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Val Kilmer is opening up about his many loves. In his new memoir, I’m Your Huckleberry, the 60-year-old actor detailed his romances with several very famous women, as well as his “most painful” heartbreak.

Kilmer famously dated Cher, Cindy Crawford, and Angelina Jolie, but in an excerpt from his book shared by People, he wrote that it was the end of his relationship with Daryl Hannah that truly devastated him.

Hannah dated Kilmer in 2001 after they met on the set of the film In God We Trust. In his book, Kilmer wrote of the happy times he spent with the Splash star in New Mexico before their split.

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

Hannah married singer Neil Young in 2018 after the two dated for four years. Interestingly, Young’s former Crosby, Stills, Nash and Young partner, David Crosby, once warned the “Old Man” singer that Hannah was a “poisonous predator” and would someday break his heart, according to an interview with Idaho Statesman. Crosby later apologized to Young.

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Dear reader. I have a crush on you. And now, more than ever want to escape with you. It’s dangerous, though based on the last 48 hours, it would seem everything is. They say when one of your five senses is compromised, you can feel the others become heightened. My speech was compromised, a few years back, but I now see and feel things I had never seen or felt before. So please indulge me, as we travel with lightning speed because I’ve led a lightning-speed life. Welcome to my book, I’m Your Huckleberry, it will be available everywhere on April 21, but you can order copies now from your favorite bookstore. Stay safe out there, reader, I'd love you along for the ride. - the man behind the book

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While Kilmer’s heart was broken by Hannah, he wrote that his ex-loves Cher and Crawford helped him through some difficult times. The actor described Cher — his girlfriend in the early 1980s — as loyal, adding that once she enters your heart she “never leaves.” He also wrote that Cher’s “steadfast love and loyalty never die.”

The Doors star also wrote that Cher was by his side following his 2015 throat cancer diagnosis and that she made him laugh during a frightening emergency situation. Kilmer revealed that the “If I Could Turn Back Time” singer invited him to stay in her guest house while his health was declining, per Fox News.

“One night, I suddenly awoke vomiting blood that covered the bed like a scene out of The Godfather, ” he wrote. “Cher stepped in and stepped up.”

Kilmer noted that after they called 911, he saw the singer checking out the handsome paramedic who arrived on the scene.

“Only in Hollywood, right?” he wrote. “Despite the fact that I was covered in blood, I caught her eye and bounced my brows like Groucho Marx. Hubba hubba. Cher was bashful to be busted but then couldn’t help laughing out loud at the audacity.”

As for Crawford, Kilmer wrote that the supermodel helped him find happiness after his divorce from ex-wife Joanne Whalley, whom he was married to from 1988 to 1996.

It’s also no surprise that Jolie — whom Kilmer worked with on the 2004 movie Alexander — is described as “the most soulful and serious” of all of his famous exes. He added that when people ask what the Oscar-winning mom of six is like, he tells them “she’s like other women and other superstars, just MORE.”