Val Kilmer 'Hadn't Had a Girlfriend in 20 Years' Despite Lengthy List of Superstar Partners

Val Kilmer's death at 65 from pneumonia left the world in mourning. Though loved ones were by his side, Kilmer quietly battled loneliness for decades, admitting in his memoir "I'm Your Huckleberry" that he "hadn't had a girlfriend in 20 years" and "felt lonely every day."

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In the early 1980s, Kilmer fell for Cher, whom he described as captivating. "We both loved laughing and went on doing so for well over a year," he wrote. Cher once said, "I was madly in love with Val Kilmer and he left." Despite their split, they remained close.

Kilmer and Michelle Pfeiffer formed a deep connection while working together, sharing personal struggles. "The secret pain that Michelle and I shared created an intimacy between us," he wrote.

With Ellen Barkin, Kilmer recalled her laugh and gentle spirit. "I remember her wit, her sultry eyes, but mostly her laugh." Their romance was short-lived but fondly remembered.

Meeting Carly Simon after the 'Top Gun' premiere, Kilmer wrote, "We talked all day about everything under the sun." He called her the woman he wanted to be with "for the rest of my life."

Joanne Whalley became Kilmer's only wife. They married in 1988 and had two children, but their union ended in 1996. Whalley cited irreconcilable differences.

Following that divorce, Cindy Crawford became a comforting presence. Kilmer said, "I thought I could have died from her love because its delight was simply too much to bear."

Kilmer was later linked to Jaycee Gossett and actress Daryl Hannah. Of Hannah, he wrote, "I cried every single day for half a year."

He also shared a bond with Angelina Jolie, writing, "I was recused from an icy inferno of solitude by another angel... Angelina."