Val Kilmer was linked to Cindy Crawford, Angelina Jolie, Cher and more celebrities over his decades-long career.

“I’ve always found women infinitely more interesting than men,” the Top Gun star wrote in his 2020 memoir, I’m Your Huckleberry. “Perhaps that’s why we’ve always gotten along. We are big oafy elephants … and they are ʙuттerflies.”

While he was in several public relationships, Kilmer has only walked down the aisle once. He married actress Joanne Whalley in 1988. After welcoming daughter Mercedes in 1991 and son Jack in 1995, they called it quits, finalizing their divorce in 1996.

While he moved on from his spouse with Crawford in the 90s, he referred to his split from Daryl Hannah, whom he dated in the early 2000s, as his “most painful” heartbreak of all.

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Kilmer also claimed that he hadn’t “had a girlfriend in 20 years. The truth is I am lonely part of every day.”

Keep scrolling for Kilmer’s complete dating history: