Val Kilmer’s Greatest Love Was an ’80s Icon

Despite romancing some of the world’s most beautiful and intriguing women in the 1980s and 90s, Val Kilmer hadn’t been in a relationship for quite a while at the time of his death at 65. He admitted in his memoir, “I’m Your Huckleberry,” that he hadn’t “had a girlfriend in 20 years. The truth is I am lonely part of every day.”

A sensitive, romantic soul, Kilmer loved fiercely, which led to several heartbreaks. Despite this, it’s rare to find an ex of his who doesn’t look back on their time together fondly.

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Kilmer Preferred the Company of Women

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

His first serious relationship was with St. Elmo’s Fire actress Mare Winningham. After a strange dream in which she was kissing someone else, he drove 300 miles to see her.

“Then, just as in my dream, coming out of the dark woods, I saw Mare and this boy kissing,” he wrote. While they broke up, the two remained friends.

Kilmer’s next big romance was with Cher, who said on The Howard Stern Show that she “was madly in love” with him. While he didn’t think they’d have anything in common, he said she was “funny, hysterically funny.” The two dated and laughed together for over a year and stayed close for the rest of his life. When he found out he had throat cancer, he was visiting Cher at her house.

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He Saw His Future Wife in a London Play

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While Kilmer was still dating Cher, he found himself in London. He went to see the play The Genius and was immediately smitten with the lead actress, Joanne Whalley. He went to the show numerous times to get a glimpse of her but was too shy to speak to her.

Kilmer dated gorgeous, fascinating women such as Ellen Barkin and Carly Simon in the following years. Then, he signed on to star in Willow and was astonished when Whalley walked in to audition.

“Even now as I see the aspiring actress walk into the room to read the lines, my heart beats as loudly as it beat three decades ago,” he wrote. Within a year, they were married.

While he and Whalley would go on to have two kids, Mercedes and Jack, before she filed for divorce years later, Kilmer felt foreboding the first couple of years. “I knew in my heart that our marriage would not last,” he wrote. “I ascribe fault to no one. I now see it as a matter of fate.”

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Cindy Crawford Helped Him Heal After His Divorce

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After splitting from Whalley, he met Cindy Crawford, who he fell head over heels for. “I thought I could have died from her love, not because it was difficult but because its delight was simply too much to bear,” he wrote.

Several years later, he worked with Angelina Jolie on Alexander. “When people ask me what Angelina Jolie is like, always say she’s like other women and other superstars, but just more,” he declared. After their relationship ended, he met Jaycee Garnet Gossett.

“Jaycee and I embarked on a three-year love affair that lives in my body-mind like nothing else,” he wrote. “She was a real-life angel, and she was up for anything, as long as it was good for the soul.” Kilmer blames his immersion in the role of Danny Parker in The Salton Sea for the relationship’s demise.

“I let the character of Parker swallow me whole, and I was miserable, desolate, without a single sparkle in my eye,” he wrote sadly. “In honor of the project and in honor of art, I let Jaycee slip away.”

Val Kilmer Admits He Cried Daily After Breakup With Daryl Hannah

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For Kilmer, Daryl Hannah was elevated above all else.

“She was kind of the female me, except better,” he wrote in his memoir. He considered her an equal to everyone and was amazed at her positive demeanor. Despite his many romances and relationships, his breakup with Hannah devastated him more than any other.

“Those kind of rip-your-heart-out relationships that had become so normal for me were just no good anymore,” he wrote.

Kilmer claimed that he cried every day for six months after they broke up for good but tried to stop when he realized he didn’t want his kids seeing him like that. “In some ways, Daryl felt like the end of that whole piece of my personality,” he wrote.