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Cher! Cindy! Angelina! ‘Top Gun’ Star Val Kilmer’s Dating History

A star-studded dating history. 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 butterflies.”

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.

“Lord knows I’ve suffered heartache,” he wrote in his book. “I knew 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 also claimed that he hadn’t “had a girlfriend in 20 years. The truth is I am lonely part of every day.”

The True Romance actor has found friendship, however, with some of his exes, including Cher, writing, “Once Cher works her way inside your head and heart, she never leaves. For her true friends, her steadfast love and loyalty never die.”

The singer, for her part, told People of her ex in 2021: “He is exasperating and hysterical. Thrilling and funny, and doesn’t do what anyone else does. I don’t know how we stayed friends, we just did. We didn’t try. We just were.”

The “Believe” singer was there for Kilmer when he was diagnosed with throat cancer in 2015. He subsequently had a tracheostomy and underwent chemotherapy and radiation treatments.

“I can’t speak without plugging this hole [in my throat]. You have to make the choice to breathe or to eat,” he said in his 2021 documentary, Val. “It’s an obstacle that is very present with whoever sees me.”

His health scare hasn’t completely halted his career as Kilmer reprised his role as Iceman in Top Gun: Maverick, which hit theaters in May 2022, alongside Tom Cruise.

“It was like no time had passed at all,” Kilmer told Entertainment Tonight in June 2022. “We blew a lot of takes laughing so much. It was really fun … special. We were all so young during the making of the first movie, but even then there was a special bond between us all.”