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Val Kilmer dated Angelina Jolie, Cindy Crawford and Cher in his day -- but, according to the actor, his breakup from Darryl Hannah was “by far the most painful.”

Kilmer dated the actress in 2001 after the pair worked together on the film, “In God We Trust,” People magazine reported on Wednesday. Hannah, 59, would go on to marry Neil Young in 2018.

Kilmer, 60, got candid about their relationship in a new memoir, titled “I’m Your Huckleberry,” which is scheduled to be released on April 21.

In the book, the star recalled how his split from Hannah was a tough experience for him behind closed doors.

“Lord knows I’ve suffered heartache,” Kilmer wrote, as reported by People. “But Daryl was by far the most painful of all. (Neil Young, I always loved you, but I’m afraid I hate you now).”

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Daryl Hannah and Val Kilmer during the 'Wonderland' Hollywood premiere at Grauman's Chinese Theater in Hollywood, California.

Daryl Hannah and Val Kilmer during the 'Wonderland' Hollywood premiere at Grauman's Chinese Theater in Hollywood, California. (Photo by Jon Kopaloff/FilmMagic/Getty)

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Kilmer also opened up for the first time about his 2015 diagnosis with throat cancer. He revealed it was Cher, whom he dated in the early 1980s, who stood by his side.

According to Kilmer, the 73-year-old invited him to stay in her guest house while his health was declining.

“One night, I suddenly awoke vomiting blood that covered the bed like a scene out of ‘The Godfather,’” Kilmer recalled.

“I prayed immediately, then called 911,” he continued. “Then alerted my hostess. Cher stepped in and stepped up.”

Kilmer added the music icon managed to make him laugh.

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Cher and Val Kilmer dated in the '80s.

Cher and Val Kilmer dated in the '80s. (Photo by Barry King/WireImage/Getty)

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“And yet even in my grave condition, I saw her scanning the paramedic, who was Gregory Peck drop-dead handsome,” shared the star. “Only in Hollywood, right? Despite the fact that I was covered in blood, I caught her eye and bounced my brows like Groucho Marx. Hubba hubba. Cher was bashful to be busted but then couldn’t help laughing out loud at the audacity.

“Here we were, joking about beauty and desire, while I looked like a stuntman from Tarantino’s ‘Reservoir Dogs’ and, yes, while my life seemed to be in mortal danger,” added Kilmer. “We laughed out loud before they finished with my vitals and shut me up with an oxygen mask.”

According to the outlet, Kilmer underwent a tracheotomy, chemotherapy and radiation. In addition, he turned to his Christian Science faith and prayed for healing.

Today, Kilmer is cancer-free.

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Actor Val Kilmer visits the United Nations headquarters in New York City, New York to promote the 17 Sustainable Development Goals (SDGs) initiative, July 20, 2019.

Actor Val Kilmer visits the United Nations headquarters in New York City, New York to promote the 17 Sustainable Development Goals (SDGs) initiative, July 20, 2019. (Photo by EuropaNewswire/Gado/Getty Images)

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“I have been healed of cancer for over four years now, and there has never been any reoccurrence,” said Kilmer. “I am so grateful.”

Kilmer’s speech has been impacted by cancer. However, he’s keeping busy by doing voice exercises every day. In addition, he’s been touring with his one-man show about Mark Twain and this summer he will reprise his role in the “Top Gun” sequel “Maverick.” The film is slated to open in theaters on June 24.

“The fact that my impeded speech could spell the end of my career only served to motivate me,” wrote Kilmer.