Inside Val Kilmer's Explosive Love-Life — From Flings With Angelina Jolie and Cindy Crawford to How Break-Ups With Cher and Daryl Hannah Left Him Weeping and Haunted for Life
Val Kilmer was not short of beautiful women in his life, dating numerous well known stars.
April 2 2025, Published 3:00 p.m. ET
As one of the most sought after heartthrobs of his time, Val Kilmer crossed paths with many beautiful starlets including Angelina Jolie and Cindy Crawford, but not all of them ended on a good note.
The actor's love life now has the spotlight on it following his devastating passing, RadarOnline.com can reveal.
Kilmer crossed paths with many beautiful women in his career.
Kilmer's 2020 memoir, I'm Your Huckleberry, detailed some of his romances from the 1980s to the 2000s, and said: "I've always found women infinitely more interesting than men.
"Perhaps that's why we've always gotten along. We are big oafy elephants … and they are butterflies."
Kilmer saw a "butterfly" in Cher when they dated from 1982-1984. He was 23 while she was 13 years older.
However, it was the Top Gun actor who walked away from the relationship.
"I was madly in love with Val Kilmer and he left," the singer revealed during an appearance on Howard Stern's SiriusXM in 2024, and made clear the movie star was one of the "few" to have ever broken her heart.
Cher, now 78, then admitted age was a big reason for the split as Kilmer was "really young."
Following his relationship with Cher, Kilmer then turned his attention to Michelle Pfeiffer. The pair met while working together on the 1985 afternoon special One Too Many and quickly became friends after exchanging thoughts about their lives.
The actor dated Cher in the early 1980s.
The Real Genius star wrote in his memoir: "The secret pain that Michelle and I shared created an intimacy between us."
Kilmer and Pfeiffer are said to have had a brief romance during the 1980s.
Also during the 1980s, Kilmer found himself falling for actress Ellen Barkin, who was six years his senior at the time.
"I remember her wit, her sultry eyes, but mostly her laugh," Kilmer wrote in his book, and recalled how soft her hair was during their romance.
He wrote: "Her hair. Who remembers the softness of a woman's hair? If you ever have a chance to consensually ever so gently touch Ellen's hair, it will be worth the look she's gonna drop on you."
The Kiss Kiss Bang Bang star remembered his relationship with Barkin as "whimsical as it was whirlwind."
Kilmer also had a brief romance with actress Ellen Barkin.
Kilmer also had romances with Carly Simon, Joanne Whalley, and Crawford.
On the supermodel, Kilmer said in 2005: "Did I date Cindy Crawford? Yeah, she's very nice. A smart girl with a great sense of humor. She's a fantastic cook, too, always carried recipes around when she traveled."
The Hollywood star – who dated Crawford for two years – recalled their breakup: "I thought I could have died from her love, not because it was difficult but because its delight was simply too much to bear."
Kilmer even had a brief fling with Jolie – the two worked together in the 2004 film Alexander.
"When people ask me what Angelina is like, I always say she's like other women and other superstars, but just more," Kilmer recalled. "More gorgeous, more wise, more tragic, more magic, more grounded. Is it worth it? Worth knowing people who require weeks of effort to understand even a little? Yes."
Kilmer's romance with Daryl Hannah, however, in 2001 left him shattered following their split.
The 'Top Gun' star also had a fling with Jolie.
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He wrote in his memoir: "I knew 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. When we finally broke up, I cried every single day for half a year."
Kilmer's daughter Mercedes Kilmer confirmed her dad died in Los Angeles on Tuesday, April 1, from complications of pneumonia following a string of health issues linked to his breathing after his body was damaged by years of chain smoking.
He was 65 years old.
Kilmer's split from Hannah left him distraught.
