As one of the 1980s’ biggest Hollywood heartthrobs, Val Kilmer certainly had his choice of the industry’s most beautiful women.
But prior to his death from pneumonia on Tuesday following a long health battle, the beloved actor revealed he ‘hadn’t had a girlfriend in 20 years’ and felt ‘lonely every day’.
The admission, in a tell-all memoir I’m Your Huckleberry, would have come as a surprise to anyone familiar with Kilmer’s star-studded dating life from the 1980s to the 2000s.
For Kilmer dated some of the world’s most famous women, seducing the likes of Cindy Crawford, Angelina Jolie and Daryl Hannah, marrying just once to Joanne Whalley.
So powerful was his charisma, that Cher even admitted he was one of the few men to have ever broken up with her.
‘I’ve always found women infinitely more interesting than men,’ Kilmer wrote in his 2020 memoir.
‘Perhaps that’s why we’ve always gotten along. We are big oafy elephants … and they are butterflies.’
But Batman star Kilmer, who was diagnosed with throat cancer in 2014, was never to find lasting happiness in love – and spent his final years alone.
Here, FEMAIL takes a closer look at Kilmer’s rollercoaster of a love life – and the one woman he never truly got over.
Cher
Val and Cher dated for two years from 1982 to 1984, when Cher was 36 and Val was 23
She later admitted he was one of the few men to ever break up with her, but they remained close friends (pictured in 1983)
Cher has dated some of the most famous names in Hollywood, including Tom Cruise, Warren Beatty and Gene Simmons.
But last November, during an appearance on Howard Stern‘s SiriusXM, she admitted Val was one of the ‘few’ to have ever broken her heart.
Stern asked, ‘Who would ever leave you?’
‘Few men, few men. A couple. Look, I was madly in love with Val Kilmer and he left,’ Cher revealed.
Stern was left baffled: ‘Why would he leave? He’s having fabulous sex with one of the most beautiful women in the world, what the f***’s the problem with this guy?’
But Cher admitted that their age gap had come into play, admitting Val was ‘really young’.
The pair dated for two years from 1982 to 1984, when Cher was 36 and Val was 23.
Their 13-year age gap raised many eyebrows in Hollywood at that time.
In 1984, Val’s career was just about to take off, as he would star in Top Gun in 1986 and .
In a 2021 interview with People Magazine, Cher said she’d fallen ‘madly in love’ with the beloved actor.
‘He’s like nobody I’ve ever known,’ she said. ‘He is exasperating and hysterical. Thrilling and funny, and doesn’t do what anyone else does.’
‘Our sense of humor, and what we would put up with from one another, was more than I think I’ve ever had with any other guy. He would just go off and do his own thing and you just had to be prepared.
‘And he was so beautiful. It went from madly in love and laughing hysterically to respecting each other’s ability.’
Having met at Cher’s birthday party, they remained friends for years after they dated.
After he was diagnosed with throat cancer, it was Cher who offered him support.
‘Once Cher works her way inside your head and heart, she never leaves. For her true friends, her steadfast love and loyalty never die,’ he wrote in his memoir.
Michelle Pfeiffer
Val and Michelle Pfeiffer are pictured on the set of One Too Many in 1985
Shortly after his whirlwind romance with Cher came to a close, Val turned his attention to Michelle Pfeiffer.
The 66-year-old American actress met Val in the 1980s while the two on the set of an ABC Afterschool Special, One Too Many, and they quickly became friends.
He said he had always felt comfortable talking to Michelle, and was able to open up to her about his parents, with who he shared a strained relationship.
In turn, Michelle was able to confide in Val the inner working of her rocky marriage to Peter Horton, from who she later divorced.
‘The secret pain that Michelle and I shared created an intimacy between us,’ he wrote in his book.
Val claimed to have adored her but confessed that he had always had an ‘all consuming crush’ on her younger sister, who ‘did not seem to reciprocate, even a little. In fact, she seemed to not even know I existed.’
While the details of their alleged romance are unclear, the pair are thought to have dated at some point during the 1980s.
Ellen Barkin
Among his pool of high profile beaus was the American actress, Ellen Barkin (pictured in 1994)
Ellen Barkin was six years Val’s senior when they dated in the 1980s. Pictured in September 2024
Among his pool of high profile beaus was the American actress, Ellen Barkin – though comparably less has been published about their relationship.
Writing in his memior, I’m Your Huckleberry, he recalled unexpectedly falling Ellen, who was six years his senior, during the 1980s.
He wrote that Emmy-winning actress had ‘the best smile in all five boroughs’, and specifically recalled the softness of her hair.
He wrote: ‘I remember her wit, her sultry eyes, but mostly her laugh,’ the Top Gun star said.
Recounting their brief romance, he gushed over: ‘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.’
He said the two enjoyed months of window-shopping on Rodeo Drive by day and barbecuing at night,’ adding that she was ‘one of the enchantresses who got away, no doubt due to my unmanageable preoccupations, my neglect.’
With Ellen, their romance was as ‘whimsical as it was whirlwind,’ he reflected.
Carly Simon
Val had wanted to be with Carly Simon (pictured in her 1972 music video for You’re So Vain) for ‘the rest of my life’
It was at the New York premiere of Top Gun in 1986 that Val met the American singer-songwriter, Carly Simon.
A week later, he would visit her at her home in the Upper West side, where he said they ‘talked all day about everything under the sun’.
Writing in his book, he said: ‘We talked about shyness. We talked about Harry Nilsson. We talked about Bob Dylan and the evils of yellow journalism and the exquisite phrasing of Frank Sinatra. We talked and talked and talked. We had dinner.’
He wrote that he the ‘You’re So Vain’ singer had invited him to spend the night at her home, where he stayed in the guest room and was woken to a tray or organic eggs and jams, adding that it was the ‘best breakfast of all time’.
‘I wanted to be with Carly every day of the rest of my life…. She had utter power over me… Our friendship flowered.
‘I think the reason we soon stopped seeing each other was her realization that it was too overwhelming for me. Her shy sensitivity saw through my soul. She saw that I was madly, hopelessly in love with her. I’m not sure I ever spoke those words, but you must have known, Carly.’
But Val said that the two drifted apart when Carly realised that Carly was hopelessly in love with her.
Joanne Whalley
Val Kilmer and Joanne Whalley, in the film Kill Me Again in a casino in Las Vegas February 12, 1989
Val met his only wife, Joanne Whalley in 1988 after meeting on the set of the film Willow (pictured)
Joanne was married to Kilmer from 1988 to 1996 – the only woman he ever married. Together they had two children – Mercedes and Jack.
The couple first met on the set of fantasy film Willow, but the married struggled due to ‘constant rumours’ around his on-set romances and reputation as a heartthrob.
However, he remained close to his children following his divorce, with Mercedes telling People: ‘My dad’s able to very artfully circumvent the limitations of his speech, so I learned so much watching him, how he communicated physically.
‘It taught me so much about acting that expanded what I thought acting was, which was central to speech.’
She was referring to her father’s speech issues, which occurred as a result of his throat cancer.
Kilmer only learned he was getting a divorce while ‘watching CNN in a hotel room’, adding that finding out was ‘no fun’.
The eventual divorce was fiendishly expensive, with Kilmer dubbing it ‘the second most expensive in New Mexico’ and came only ‘two months after the birth of their second child’.
For their 1995 split, Joanne cuted ‘irreconcilable differences’ as the reason for their marriage, with many believing it had struggled due to Val’s sex symbol status.
Cindy Crawford
Val was looking for a shoulder to cry on following his divorce from Joanne Whalley – and found solace in Cindy Crawford (pictured 1996)
After divorcing Joanne Whalley in 1996, Val was undoubtedly looking for a shoulder to cry on.
And there to be that shoulder was Cindy Crawford, who went on to date the actor for two years
Val has previously credited the now 59-year-old model with having supported him through his divorce.
Speaking to The Guardian in 2005, he said: ‘Did I date Cindy Crawford? Yeah, she’s very nice. A smart girl with a great sense of humour.’
‘She’s a fantastic cook, too, always carried recipes around when she travelled,’ he added.
His memories of the star are clearly fond. Describing her after their breakup, he said: ‘I thought I could have died from her love, not because it was difficult but because its delight was simply too much to bear.’
‘You have to be committed with a woman that’s as dynamic and as committed to their work as someone like Cindy Crawford who was the number one model on the planet at the time,’ he told Good Morning America of their romance in 2020.
Daryl Hannah
Val Kilmer admitted he ‘cried every single day for half a year’ following his break-up from Daryl Hannah (pictured in 2003)
In his memoir, Val admitted he’d suffered from much heartache in his time, but admitted Daryl Hannah was ‘by far the most painful of all’, even though they never married.
Writing about The Fury actress, 64, he revealed he couldn’t stop crying after their break-up.
‘I knew I would love her with my whole heart forever and that love has lost none of its strength,’ he wrote.
‘I am still in love with Daryl. When we finally broke up, I cried every single day for half a year.’
The pair dated in 2001 after working on the film In God We Trust. She later married Neil Young in 2018.
‘Neil Young, I always loved you, but I’m afraid I hate you now,’ Kilmer added in his memoir.
Despite dating a plethora of stunning women in his youth, Kilmer admitted he hadn’t had a girlfriend in ’20 years’, adding ‘the truth is I am lonely part of every day’.
Angelina Jolie
Angelina Jolie pictured as Queen Olympias, with Val Kilmer as Philip, and Colin Farrell as Alexander the Great
Val Kilmer and Angelina Jolie during ‘Alexander’ Los Angeles Premier in 2004
In his 2020 memoir, Kilmer admitted he was a ‘slave to love’ and recalled flings with some of the world’s most famous women, including Angelina Jolie.
In I’m Your Huckleberry, the star opened up about their ‘tragic’ and ‘soulful’ fling, which began when they first crossed paths on the set of their film Alexander.
Val wrote how he ‘couldn’t wait to kiss her’ when they were on set together, saying he also wanted to ‘buy her a Gulfstream jet and have V+J painted in rainbow glory on the trail’.
‘We developed a friendship,’ he wrote in his book.
‘I was around when Angie’s mom [Marcheline Bertrand] was losing her battle with cancer. They were living in her mom’s favorite hotel. Or maybe it was Angie’s. I happened to be staying there myself. It was meaningful and mortal and effortless and exquisite.’
They didn’t begin dating until after it was released in 2004, when Kilmer said she ‘released’ him from his ‘solitude’.
He wrote: ‘I was recused from an icy inferno of solitude by another angel. Perhaps the most soulful and serious of them all. Angelina.
‘When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more.
‘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.’
However their relationship faded and shortly after Angelina would meet Brad Pitt while filming Mr & Mrs Smith, while he was still married to Jennifer Aniston.
They started dating, becoming Brangelina, and together raised all six of their kids together until they called it quits in 2016.
