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Val Kilmer left no stones unturned when he wrote his memoir,I’m Your Huckleberry, which was released in 2020. With a title ripped off from one of his famous lines inTombstone, the book was a brutally frank, tell-all tale of Kilmer’s life, including his love, loss, and regret. In one of his confessions in the book, the Batman Forever actor revealed his crush on co-star Angelina Jolie.

Kilmer worked together with Jolie in the 2004 film,Alexander. Both the actors had supporting roles in the film, playing Philip II of Macedon and Queen Olmypias, the feuding father and mother of Alexander the Great. Interestingly, Kilmer wanted a kissing scene with Jolie in the film and even jokingly told director Oliver Stone about it.
Val Kilmer Secretly Couldn’t Wait To Kiss Angelina Jolie InAlexander
Val Kilmerwrote about a secret crush onAngelina Joliewhile filming the 2004 movieAlexanderin his memoirI’m Your Huckleberry. Kilmer and Jolie didn’t have many combination scenes in the film, let alone a romantic scene. But that didn’t stop him from talking to the director about including flashback scenes that showed their character’s passionate romance.
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Kilmer shared in his book thathe couldn’t wait to kiss his co-star. He even went on to share that he would have bought her a Gulfstream jet with their initials ‘V+J’ painted on the tail. He revealed that at the time of filming, Jolie had just adopted Maddox and she was the postmodern Madonna according to the paparazzi. TheTop Gunactor wrote in his memoir (via PEOPLE):
I couldn’t wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail. She had recently adopted her first child, Maddox, and the paparazzi were obsessed with this postmodern Madonna, the perfect picture of unapproachable stardom and impossibly chic maternal instinct.

Oliver Stone, the director ofAlexander, didn’t get why Kilmer talked to him about including the flashback scenes. Kilmer tried to clarify that it was a joke but Stone didn’t exactly pick up on the humor as Kilmer had hoped. Finally, he explained,“I just dig her, Oliver. It would be nice if we had some flashbacks when they were in love and happy together.'”
While Kilmer’s crush doesn’t count as a romantic relationship between the couple, some media speculated that the two had a very short-lived dating history (via Cosmopolitan). Jolie went on tomarry and divorce Brad Pitt, while Kilmer remained single.

Val Kilmer Also Opened Up About His Most Painful Heartbreak
Kilmer revealed in his memoir that he was a hopeless romantic. He also went on to name a few women who were involved with him, including Cher, Cindy Crawford, and Carly Simon. But the one that shattered his heart the most wasKill Bill: Vol. 2actress Daryl Hannah. The two briefly dated in 2001 but the lost love had a deeper impact on Kilmer.
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He shared that he cried every day for half a year. He went on to proclaim his everlasting love for the actress, who married singer Neil Young in 2018. Kilmer shared in his memoir (via PEOPLE):
Lord knows I’ve suffered heartache. But Daryl was by far the most painful. 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 revealed that he was without a girlfriend for 20 years at the time of writing his memoir. He was married to actress Joanne Whalley in 1988. The couple divorced in 1996 and share two children — 28-year-old daughter Mercedes and 24-year-old son Jack.
Hashim Asraff
Senior Writer
Articles Published :3017
Hashim Asraff is a Senior Entertainment Writer at FandomWire, with over 2,800 articles published on celebrity culture, comic book movies, and major TV franchises. With a background in Sociology and a keen interest in pop culture, Hashim brings a unique lens to breaking news stories, character deep-dives, film rankings, and fan-driven perspectives.His coverage often includes the MCU, DCU, hit network shows, and celebrity profiles, giving readers a rich blend of entertainment and analysis. A longtime fan of crime and investigative series, Hashim has watched thousands of episodes of NCIS, Criminal Minds, Law & Order: SVU, Bones, Blue Bloods, and The RookieA passionate storyteller and wordsmith, Hashim has also worked as a ghostwriter and managed multiple social media handles. He brought his writing expertise to FandomWire to also pursue his lifelong love for cinema and television.
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