Val Kilmer's list of A-list lovers was as impressive as his film credits – but here's why he was single when he died

Yahoo

03-04-2025

Val Kilmer was a Hollywood star in the classic mold, known for his big movies — 'Top Gun,' 'Tombstone' and 'Batman Forever' — as well as his love affairs. Some succeeded, some failed, but they were never dull.
The square-jawed heartthrob — whose family announced he died of pneumonia Tuesday, following an 11-year battle with throat cancer — romanced Cindy Crawford, Angelina Jolie, Ellen Barkin and, most notably, Cher.
During the eccentric star's heyday in the '80s and early '90s, he was a Tinseltown chick magnet of the highest order, drawing the smartest, coolest and most beautiful of Hollywood.
Director Brett Ratner says Kilmer's personality as much as his leading-man looks made him alluring to filmmakers as well as the opposite sex.
'He wasn't a normal guy. His charm, on the screen and off, was amazing. And the devotion to his craft was 200%,' Ratner told The Post. 'He was charming, funny and talented.'
Los Angeles-born Kilmer's sparkling combination did the trick for Cher, his first big-time girlfriend. He was 21 and had just finished at the Juilliard acting school in New York, she was in her mid-30s when they connected at a birthday party.
In his autobiography, 'I'm Your Huckleberry,' Kilmer talks about the singer whisking him off to a top-story suite at Caesars Palace in Las Vegas during their whirlwind romance.
'I was smitten (and flattered and aroused and exhilarated) to be with so glamorous a star … Maybe the decision to leave New York and go to Hollywood with Cher was easy,' he wrote.
For her part, Cher talked about being 'madly in love' with Kilmer and recalled how they enjoyed 'fabulous sex,' on 'The Howard Stern Show' last November.
However, she told People magazine they were each 'alpha males,' and 'both individuals … neither of us was going to give up on that.'
She said the footloose ladies' man was one of the very few who ever left her. 'Sometimes you're only meant to stay with someone so long … And Val was really young,' Cher has lamented.
However, they remained friends and she nursed him after he was diagnosed with throat cancer in 2014.
Kilmer's next Hollywood conquest, 'Sea of Love' actress Ellen Barkin, beckoned as his career started to blow up. In 1986, he co-starred in 'Top Gun' alongside Tom Cruise and was clearly a star on the rise.
Their relationship was Hollywood chill — Kilmer described him and Barkin spending their time together 'window-shopping on Rodeo Drive and barbecuing at night.'
His favorite features of the Bronx-born actress with the husky voice? Her hair and her stare. '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.
But again, things fell apart, with Kilmer blaming his 'unmanageable preoccupations' and 'neglect' for the relationship ending.
This is little surprise considering Kilmer's all-immersive approach to acting. When he auditioned for his first big flick, 'Top Secret!,' he dressed up as Elvis Presley for the audition — a role he'd finally get to perform in scenes for 'True Romance' in 1993.
One of Kilmer's most iconic and lauded performances came playing another rocker, Jim Morrison, in the 1991 rock 'n' roll biopic 'The Doors.'
To prepare for the lead role of the hell-raising, hard-drinking Morrison — known as The Lizard King — Kilmer learned to sing 50 Doors songs and recorded them in LA studios. He then brought the tapes to various members of The Doors to see if they could tell the difference between him and Morrison. Some members could not, according to Kilmer.
His method approach was not relegated only to singing. 'It's fun to jump on people and get paid for it — which [Morrison] did,' Kilmer told David Letterman during a 1992 appearance on 'Late Night.'
Later, he called the role the toughest he ever took on, writing, 'Jim was suicidal and when you spend over a year rehearsing inside someone's skin who is so deeply unhappy … it's tough. Also he just picked the wrong toolbox to make his creations. Booze is a classic dead end. But the poetry was glorious,' in a 2017 Reddit Ask Me Anything.
However, at the time of filming, Kilmer had found more stability in his personal life, in his relationship with British actress Joanne Whalley.
They had met in 1987 while filming 'Willow' in the UK. In his book, he describes wooing Whalley in an unusual way — by flying another woman, his then-girlfriend, who was 'the unequivocal idea of beauty, an American sweetheart.'
The plan was to impress Whalley by bailing on his squeeze, an eccentric stunt that worked.
The couple married in 1988 and had two children, Jack, now 29, and Mercedes, now 33. However, not long after the birth of their daughter in 1995, they divorced.
Kilmer was dumped as cheekily as Whalley was wooed. 'I learned about her decision to divorce while watching television in Ireland,' he wrote in his autobiography.
Still basking in the fame brought about by his starring role in that year's 'Batman Forever,' he wrote, 'It was broadcast on CNN as a hard news story.'
Coming onto the scene to soothe his broken heart: supermodel Cindy Crawford. Their relationship was another whirlwind, this one lasting two years. Of his time with her, he remembered how she used to prepare his favorite dish, salmon, at her home in Malibu. They first fantasized about how they'd decorate an imaginary ranch together; then they moved to a real one in New Mexico.
Kilmer maintained his relationship with the model was a 'cat and mouse game.' She was always on the go, while he wanted her to be around.
That relationship, he wrote, ended with a conversation. They were mannered and adult about it, but just incompatible. On the other side of things, his bust-up with Daryl Hannah was something else altogether.
They had met on the set of 'In God We Trust,' in which they co-starred in 2001. It was a superstar relationship where they attracted the flashbulbs wherever they went and attended the Grammys and the Oscars together, skied in Telluride and then retreated to the ranch in New Mexico, which he kept after the split from Crawford.
Through it all, though, Kilmer figures he was overly possessive. Their breakup is the one that hit him the hardest.
'Lord knows I've suffered heartache with women,' he wrote in his book. 'But Daryl was by far the most painful of all. Suffice to say, I would have done anything to win her back.'
Busted up as Kilmer's heart may have been, he still had room for one more great celebrity romance in his life. True to form, he met the beguiling Angelina Jolie on the set of 'Alexander.'
The 2004 movie may have boasted a heavily A-list cast — including Colin Farrell in the titular role as Alexander the Great and Anthony Hopkins — but is regarded as a bit of a trifle.
Reprising with Oliver Stone — who also directed him in 'The Doors' — Kilmer hatched another offbeat plan to romance Jolie.
She was playing Alexander's mother while he was the father, so Kilmer told Stone he'd take the role under one condition: He and Jolie needed to 'have flashbacks to falling hard for each other and storming the castle with passion, before turning against each other.'
Stone played along and the plan panned out. Kilmer and Jolie became an item. He described her as 'the most soulful and serious of them all.'
Ultimately, though, life imitated art. The relationship was short-lived and — despite the fact that Kilmer 'couldn't wait to kiss her' and 'buy her a Gulfstream jet' — he was no match for Jolie's next conquest: Brad Pitt.
Pitt — then the biggest actor on the planet, with much more star power than Kilmer — met Jolie on the set of 'Mr. and Mrs. Smith' (while he was still married to Jennifer Aniston). The rest of that story is Hollywood history.
After that leading lady, Kilmer's love life seemed to fizzle out and he instead decided to dedicate his time to his craft as an actor and painting suitably eccentric artworks as his focus in life. In 2020, he admitted he 'hadn't dated in 20 years.'
A practicing Christian Scientist, Kilmer's voice — one of his most valuable assets as an actor — took a hit after he was diagnosed with throat cancer in 2014.
He had started performing the one-man play 'Citizen Twain,' which he also wrote and directed, at various theaters around the country in 2010, to great reviews.
However, by 2015, audiences became shocked at his scratchy tone and diminished voice, and he had begun to hide his neck under scarves. Eventually he revealed his diagnosis in 2017.
Although his latter years were largely lived away from Hollywood, Kilmer did make 'Cinema Twain,' a movie version of his stage show, in 2019, and in 2021, a documentary on his life using years of archive footage, 'Val,' was released.
When a sequel to 'Top Gun' was finally made in 2022, Kilmer had a part, with his voice digitally created through AI trained on old clips.
Kilmer's art was also a dominating factor in his life. He maintained a warehouse where he provided space for younger artists, exhibited his work and did not relegate his painting surfaces to canvas. While working on 'I'm Your Huckleberry,' he proved as much to co-author David Ritz.
'David is bald,' the book's agent, David Vigliano, told The Post. 'At one point, Val took a magic marker and drew on David's head. I don't remember what he drew, but I do remember that David loved it.
'He thought it was funny and sweet and in keeping with Val's sweet, freewheeling nature.'
Thinking back on the time he spent with Kilmer and some of the elements that attracted women, from Cher to Daryl Hannah to Angelina Jolie, Vigliano added, 'Val was just a gentle, creative, loving guy.'