Val Kilmer had a string of high-profile relationships after soaring to fame in the 1990s but shared his upset over not finding love later in life.

The Hollywood icon died at the age of 65 on Tuesday after a long health battle, his daughter Mercedes Kilmer confirmed.

Following the sad news of his death, Kilmer’s heartbreaking comments about how ‘lonely’ he felt in his later years have reemerged.

In his 2020 memoir, I’m Your Huckleberry, Kilmer shared his desire for a relationship and revealed he had been single for around 20 years.

‘I haven’t had a girlfriend in 20 years. The truth is I am lonely part of every day,’ he emotionally wrote.

‘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 ʙuттerflies.’

Val Kilmer (pictured in July 2019) had a string of high-profile relationships after soaring to fame in the 1990s but shared his upset over not finding love later in life 

Kilmer was married to actress Joanne Whalley (both pictured in 1989’s Kill Me Again) from 1988 until 1996 and they share two children – a daughter Mercedes, 33, and a son Jack, 29

Kilmer was married to actress Joanne Whalley from 1988 until 1996 and they share two children – a daughter Mercedes, 33, and a son Jack, 29.

The couple reportedly struggled due to ‘constant rumors’ around his on-set romances and reputation as a heartthrob.

Their divorce was fiendishly expensive, with Kilmer dubbing it ‘the second most expensive in New Mexico’ and it came only two months after the birth of their son.

They cited ‘irreconcilable differences’ as the reason for their divorce and Joanne was the only woman he ever married, despite his star-studded relationship history. 

During his Hollywood heyday, Kilmer had notable relationships with huge stars including Cindy Crawford, Angelina Jolie, Cher and Daryl Hannah.

However, the high-profile flings were all short-lived, though he remained very close friends with Cher over the years and she supported him after his cancer diagnosis.

Cher revealed that Kilmer was one of the ‘few’ to have ever broken her heart, telling Howard Stern’s SiriusXM: ‘I was madly in love with Val Kilmer and he left.’

Cher revealed their age gap had come into play, admitting Kilmer was ‘really young’ as he was just 23 at the time of their two-year romance, while she was 36.

Kilmer was single ever since his devastating split from Daryl Hannah (pictured) and hoped for another relationship in his later life, admitting he was ‘lonely’ in his later years

Read More Hollywood stars pay tribute to ‘brave’ Val Kilmer in emotional posts after death at 65

But Kilmer also suffered much heartache during his life, describing Daryl Hannah as ‘by far the most painful of all’.

‘I knew I would love her with my whole heart forever and that love has lost none of its strength,’ he wrote in his memoir.

‘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.

Kilmer has been single ever since his devastating split from Hannah and hoped for another relationship in his later life.

He was diagnosed with throat cancer in 2014 and his ex-girlfriend and close friend Cher rallied around to support him at the time.

Kilmer was unaware he had throat cancer until one day he coughed up ‘coagulated blood’ and called for an ambulance before pᴀssing out.

He then woke up in a Santa Monica hospital after an emergency tracheotomy – where a hole is created in the neck and windpipe for a tube to be inserted to breathe.

During his Hollywood heyday, Kilmer had notable relationships with huge stars including Cher (pictured in 1990), who remained his close friend and supported him in his 2014 cancer battle

In his memoir, Kilmer told how ‘Cher stepped in and stepped up’ after he was hospitalized and was able to cheer him up even during the difficult time. 

‘Even in my grave condition, I saw her scanning the paramedic, who was Gregory Peck drop-ᴅᴇᴀᴅ handsome. Only in Hollywood, right?’ he wrote.

‘Despite the fact that I was covered in blood, I caught her eye and bounced my brows like Groucho Marx, hubba hubba. 

‘Cher was bashful to be busted but then couldn’t help laughing out loud at the audacity. 

‘Here we were, joking about beauty and desire, while I looked like a stunt man from Tarantino’s Reservoir Dogs and, yes, while my life seemed to be in mortal danger, we laughed out loud before they finished with my vitals and shut me up with an oxygen mask.’

After he was released from hospital, Cher allowed him to move into her Malibu guest house. 

‘Once Cher works her way inside your head and heart, she never leaves. For her true friends, her steadfast love and loyalty never die,’ Val added.

The cancer caused his tongue to swell and block his lymph pᴀssages and after the surgeries, Kilmer had to put a finger to the aperture in his throat to speak and be understood.

Kilmer underwent two tracheotomies amid his cancer battle, which affected his ability to speak. He had to use an electronic voice box to communicate afterwards 

The Hollywood icon died at the age of 65 on Tuesday after a long health battle, his daughter Mercedes Kilmer (both pictured in November 2019) confirmed 

Read More How Val Kilmer’s voice changed after throat cancer left him using voice box

Kilmer revealed he had been free of cancer for four years in 2020, but the tracheotomies permanently affected his ability to speak. 

He lost his natural voice and used an electronic voice box to communicate.

Kilmer died from pneumonia at the age of 65 in Los Angeles on Tuesday after a long health battle.

He is survived by his daughter Mercedes, 33, and a son Jack, 29, who he shared his his ex-wife Joanne Whalley. He was married to Joanne from 1988 until 1996. 

Kilmer was one of Hollywood’s most prominent leading men in the 1990s before numerous spats with directors and co-stars and a series of flops dented his career.

‘When certain people criticize me for being demanding, I think that’s a cover for something they didn’t do well. I think they’re trying to protect themselves,’ Kilmer told the Orange County Register newspaper in 2003.

‘I believe I’m challenging, not demanding, and I make no apologies for that.’

He made his film debut starring in the spy spoof Top Secret! (1984) before appearing in the goofy comedy Real Genius (1985). 

He then rocketed to stardom as Tom Cruise’s co-star in the smash 1986 hit Top Gun and was also famed for playing Batman/Bruce Wayne in 1995’s Batman Forever.

Despite his acclaimed career, Kilmer never received an Oscar or Emmy nomination, with his closest brush with a major award being a 2012 Grammy nomination for Best Spoken Word Album for The Mask of Zorro.