“The Perfect Picture Of Unapproachable Stardom”: Val Kilmer Desperately Wanted To Kiss Angelina Jolie In 1 Movie That He Begged Director To Include ‘Flashbacks’


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 in Tombstone, 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 In Alexander

Val Kilmer wrote about a secret crush on Angelina Jolie while filming the 2004 movie Alexander in his memoir I’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.

Kilmer shared in his book that he 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. The Top Gun actor 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 of Alexander, 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 to marry 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 was Kill Bill: Vol. 2 actress Daryl Hannah. The two briefly dated in 2001 but the lost love had a deeper impact on Kilmer.

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.