Val Kilmer’s Star-Studded Love Life: Cher, Cindy Crawford, Angelina Jolie, and 20 Years of Solitude

Val Kilmer, the beloved actor known for his roles in "Top Gun" and "Batman Forever," had a dating history that reads like a Hollywood dream list. From Cher to Cindy Crawford, Angelina Jolie, and more, Kilmer's romantic escapades were as dazzling as his film career. Yet, he revealed in his memoir, "I’m Your Huckleberry," that he spent the last 20 years of his life without a girlfriend, admitting, "The truth is I am lonely part of every day." Kilmer passed away this week at 65, leaving behind a legacy of both cinematic brilliance and a uniquely fascinating personal life.

One of his most iconic relationships was with Cher in the early 1980s. The singer, who described him as "brave," "funny," and "brilliant," shared heartfelt tributes after his passing, even recalling their playful nicknames for each other, "Valus Maximus" and "Cherus Reprimandus." Cher supported him during his throat cancer battle in 2015, hosting him in her guesthouse and even lightening the mood with her characteristic wit.

Another notable romance was with Carly Simon, who Kilmer once described as having "utter power" over him. He confessed in his memoir that he had been "madly, hopelessly in love" with her, despite the relationship ending due to its overwhelming intensity.

Ellen Barkin, who Kilmer dated in the late 1980s, also left a lasting impression. In his memoir, he reminisced about her captivating laugh and soft hair, calling her one of the "enchantresses who got away." This poetic sentiment seems to be a recurring theme in his reflections on past loves.

Kilmer's marriage to English actress Joanne Whalley marked a significant chapter in his life. The couple met on the set of "Willow," had two children, and were married for eight years before their divorce in 1995—a moment Kilmer discovered through CNN while visiting Marlon Brando. Talk about a dramatic twist straight out of a Hollywood script!

Following his divorce, Kilmer found comfort in the arms of Cindy Crawford, fresh off her own split from Richard Gere. In his memoir, he expressed his deep affection for her, describing her love as "too much to bear" and helping him through his heartbreak.

Perhaps the most heartbreaking of Kilmer’s relationships was with Daryl Hannah. He admitted that she caused him the most pain, and after their breakup, he cried daily for six months. His witty jab at Neil Young, who married Hannah in 2018, saying, "I always loved you, but I’m afraid I hate you now," reveals Kilmer’s sharp sense of humor, even in the face of emotional turmoil.

Finally, his brief romance with Angelina Jolie while filming "Alexander" was marked by admiration and awe. Kilmer described Jolie as "more gorgeous, more wise, more tragic, and more magic" than anyone else, capturing the essence of her superstar allure.

Val Kilmer’s love life was as colorful and passionate as his acting career, filled with moments of joy, heartbreak, and reflection. After battling throat cancer and finding humor even in his darkest times, he passed away from pneumonia, leaving behind a legacy of unforgettable performances and deeply human stories.