VAL Kilmer spent the last 24 years of his life single despite having a string of public relationships with some of Hollywood's brightest stars.
He made a heartbreaking revelation about his faltering love life in the years before his tragic death as he admitted to feeling "lonely every day".
The Batman and Top Gun star passed away at the age of 65 in Los Angeles on Tuesday after suffering from pneumonia.
He was surrounded by his family and friends when he was pronounced dead but a wife or close lover was notably absent from his bedside.
Kilmer spent almost two and half decades living alone without a partner despite having one whirlwind marriage and several other high profile Hollywood relationships.
He was always viewed as a Casanova to those who knew him with many of his on-screen flings turning into lovers in the 80s, 90s and even into the early 2000s.
In a heartbreaking admission later on in the book, he stated: "I haven’t had a girlfriend in 20 years.
"The truth is I am lonely part of every day."
Kilmer was once considered to be a Hollywood heartthrob with his most well known relationship ending up in a marriage and two children.
Kilmer met Joanne Whalley in 1987 when they paid acted alongside each other in the hit film Willow.
They started dating shortly after filming and quickly tied the knot just a year later.
Joanne, an actress from Salford, Greater Manchester, was seen to many as the love of Kilmer's life when the pair announced the birth of baby girl Mercedes in 1991.
Less than four years later, Joanne welcomed young Jack into the world.
A year later, the couple announced a shock split as they both amicably went their separate ways and divorced.
Kilmer would also date hit maker Cher, actress Michelle Pfeiffer and supermodel Cindy Crawford.
Despite the a-list names in his dating history, Kilmer always confessed to loving and missing one woman the most.
His short lived relationship with actress Daryl Hannah in 2001 was particularly impactful to the actor.
He said years after they split: “Lord knows I’ve suffered heartache. But Daryl was 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. I am still in love with Daryl.”
The breakup was so devastating that Kilmer even admitted: “I cried every single day for half a year.”
Hannah would go on to marry Neil Young in 2018 with the pair still together today.
After the heartache of his split from Hannah, Kilmer only managed to have one final foray in the dating pool.
In 2004, he again grew close to a co-worker on the set of “Alexander” when he met actress Angelina Jolie.
He described her as “perhaps the most soulful and serious of them all”.
Adding: “She’s like other women and other superstars but just more.
"More gorgeous. More wise. More tragic. More magic. More grounded.”
Their relationship faded shortly after Alexander was released when Angelina met Brad Pitt on the set of Mr & Mrs Smith.
Inside Kilmer's incredible career
The actor spent 38 years rubbing shoulders with some of the world's biggest movie stars from Robert De Niro and Al Pacino to Robert Downey Jr and Tom Cruise.
He first appeared in slapstick comedy Top Secret! in 1984 before landing a role in Top Gun two year later as his career took off.
In 1988, he played the lead role in Willow alongside his former wife Joanne before starring in a string of 90s classics.
He played Jim Morrison in The Doors in 1991 before featuring in Quentin Tarantino's second ever screenplay True Romance in 1993.
Kilmer arguably had the best year of his life in 1995 as he played the role of Bruce Wayne and Batman and starred in Heat alongside legendary duo Al Pacino and Robert De Niro.
Throughout the next 20 years, Kilmer started to play a range of role in musicals, TV shows and even doing voice overs for children's movies.
These included Knight Rider, Planes and The Ten Commandments before his final brief role back in the Top Gun universe in 2022.
He had to bravely fight to return to the big screen for Top Gun: Maverick after almost a decade battling with serious health issues.
In 2014, he was diagnosed with throat cancer and left needing a voice box to speak.
Kilmer underwent major surgery including a tracheotomy which significantly impacted his speech but ultimately helped him defeat the disease.
