However, Cher was surprised because Val was the one who took the step to break up, something that left the Oscar winner puzzled as it was the first time a man had left her. "I was madly in love," the singer admitted on The Howard Stern Show. The age difference was cited as a reason, as Cher was 13 years older.
Next came singer Carly Simon (81) -her father was the co-founder of the publishing house Simon & Schuster- whom he said in his biography I'm Your Huckleberry: A Memoir that he "wanted to be with Carly every day for the rest of my life." But their romance didn't last. In 2017, on his Twitter account, the star of Batman wrote that "once Carly Simon woke me up in her guest room with breakfast and an acoustic guitar, played me a new song she had just written. I cried. An angel...". During that time, he also dated actress Ellen Barkin (70).
While filming Willow (1988), he met his co-star Joanne Whalley (63), a prominent British actress whom he fell in love with instantly. They married in March 1988, and following the wedding, Joanne moved to Los Angeles. The couple had two children, Mercedes (33) -who announced the actor's death- and Jack (29), who have been the two driving forces in his life. That sweet marriage ended in July 1995 when the British actress cited irreconcilable differences. This happened two months after the birth of their child.
Anecdotal to the case is that Kilmer found out about the divorce while watching CNN in a hotel room, which did not sit well with him. To The Tampa Bay, he confessed that his was the second most expensive divorce in New Mexico. The divorce process was very bitter for both, but especially for the actor, as his ex-wife demanded high financial provisions.
During the paperwork, Val started dating Cindy Crawford (59). In an initial agreement, Joanne agreed for Val to pay her $27,000 monthly for child support, but a few years later, there were some missed payments that led the actress to demand ownership of the family ranch in New Mexico. That tremendous dispute forced the Hollywood star to put the property up for sale for $33 million in 2009, but after several price reductions, he finally sold it for $18.5 million to an oil tycoon. Over the years, Kilmer and Whalley managed to maintain a cordial relationship.
After Crawford, one of the fabulous top models of the 90s, came producer Jaycee Gossett, with whom he dated for two years. Of all his romances, the one that hurt him the most was the one he had with Daryl Hannah (64), as when she ended it, "I cried every day for six months," the actor admitted in his autobiography.