Val Kilmer Opens Up About ‘Most Painful’ Heartbreak And It’s Not Ex Angelina Jolie

Val Kilmer dated Angelina Jolie, but she’s not his most painful heartbreak.

The “Top Gun” star has nothing but praises for the “Maleficent” actress. He even likened Brad Pitt’s ex-wife to an angel, but Kilmer cried hard for another woman.

In his memoir, “I’m Your Huckleberry,” he detailed his relationship with various women and confessed that he was a hopeless romantic. Kilmer said he couldn’t wait to kiss Jolie and could have died from Cindy Crawford’s love. He also said he was “hopelessly in love” with Carly Simon. However, none of them made him cry daily for half a year save for Daryl Hannah, the woman who broke his heart the most.

“Lord knows I’ve suffered heartache. But Daryl was by far the most painful,” Kilmer wrote.

“I know 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.”

Kilmer and Hannah briefly dated in 2001, but he never got over her. He hasn’t had a girlfriend for 15 years already.

In his memoir, he mentioned how Jolie saved him and how people were very interested in the “Eternal” star.

“I was rescued from an icy inferno of solitude by another angel,” Kilmer wrote. “Perhaps the most soulful and serious of them all. Angelina.”

“When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more,” he continued. “More gorgeous. More wise. More tragic. More magic. More grounded. Is it worth it? Worth knowing people who require weeks of effort to understand even a little? Yes.”

Kilmer also admitted that he was excited to film with Jolie. They starred in Oliver Stone’s movie “Alexander.” He even joked to the director that their characters should fall hard for each other and storm the castle with passion before turning against each other, but “he didn’t pick up on the humor.”

He also mentioned Cher in his book and said that he found her “less-than-fascinating character of out the gossip rags.” He wasn’t motivated to meet Cher not because he wanted to snub her. He just felt that they had nothing in common.

However, when they eventually met he realized that they both loved laughing. He even described her to be the “funniest woman I ever met.” Their on-again, off-again relationship lasted for a few years before they decided that they were better off as friends.