The Woman Val Kilmer Loved Most Before His Death at 65 – He 'Cried Every Single Day' After Their Breakup

He dated some of the most iconic women in Hollywood, but only one left Val Kilmer truly heartbroken. In his memoir, released before his death, the actor opened up about the woman who changed his life — and the pain he carried long after she was gone.

He was once the face of Hollywood's golden boys — brooding, bold, and unforgettable in roles like Jim Morrison, Doc Holliday, and Batman. Val Kilmer attracted just as much attention off-screen, particularly for his love life.

But beneath the surface of his star-studded relationships was one romance that lingered long after it ended. In his memoir, Kilmer revealed a heartbreak that stayed with him for decades — one so raw he struggled to move on, even as the woman he lost found love again.

The Love Val Kilmer Couldn't Let Go

On April 1, 2025, the entertainment industry lost one of the greats as the news broke that Kilmer had passed away in Los Angeles at 65. According to his daughter, the cause was pneumonia.

Although he had been diagnosed with throat cancer in 2014, the actor later recovered and continued to work and open up about his health struggles.

In addition to being outspoken about his battle with throat cancer, Kilmer's love life drew nearly as much attention as his film career. Over the years, he was linked to some of Hollywood's most famous women.

Their relationship, the actor admitted, left a permanent scar.

Despite the headlines, the relationship that affected him most deeply was with actress Daryl Hannah. Hannah, who rose to fame in the 1980s, is known for her roles in some of the decade's most memorable films.

She played the mermaid Madison in the romantic comedy "Splash," starred as Pris in the science fiction classic "Blade Runner," and portrayed Elle Driver in Quentin Tarantino's "Kill Bill" series.

Her versatility and unique on-screen presence made her a fixture in mainstream and cult cinema. She and Kilmer began dating in 2001 after working together on the film "In God We Trust," and their bond quickly turned into something far more intense than a brief Hollywood romance.

In his memoir "I'm Your Huckleberry," Kilmer looked back on their time together with a sense of reverence and sorrow, writing:

"I would love her with my whole heart forever. That love — invisible, ephemeral, and infinite — has lost none of its strength. I made mistakes with Daryl. Maybe it was possessiveness. Maybe it was ego."

Their relationship, the actor admitted, left a permanent scar. "But Daryl was by far the most painful of all. Suffice it to say, I would have done anything to win her back. God's perfect plan of peace sometimes cannot be understood yet must be followed," he wrote.

Kilmer didn't hold back when writing about the depth of their connection, sharing, "Losing Daryl felt like the end of that whole piece of my personality. We loved deeply and fought deeply and every day with her was that unique once-a-decade spring when there's a beautiful storm followed by a priceless rainbow [...]."

He also described how the aftermath of their breakup consumed him emotionally, adding:

"I cried every single day for half a year at least, until I became very concerned about my kids seeing me that way. I thought, Grow up. I couldn't do it anymore, and I couldn't do it to them."

Years after their separation, Hannah remained a constant in his memory. The actor revealed, "I don't want to stop talking about Daryl. I want to remember the morning we awoke in her exquisitely refurbished barn in Telluride. Leaning against a wall was a remarkable piece of art, a long, wide plank of wood."

He spoke more broadly about his beliefs on love and the emotional qualities he admired most, saying, "I am a slave to Love. I am a hopeless romantic. I haven't had a girlfriend in twenty years."

For Kilmer, women were the more emotionally nuanced and engaging gender. He wrote, "The leading qualities of Love, empathy, compassion can be more easily found in a woman than a man or a feminine makeup than masculine. I've always found women infinitely more interesting than men."

In his memoir, released in 2020, Kilmer further revealed that he hadn't had a girlfriend in 20 years. Hannah, on the other hand, eventually moved on and built a life with Canadian rock musician Neil Young.

According to reports, the two met in 2014 and formed a bond through their shared dedication to environmental activism. Early in their relationship, they partook in protests, including a march in Washington, D.C., opposing the Keystone XL pipeline.

Their romance led to a private wedding on July 27, 2018, aboard Young's boat, the W.G. Ragland, anchored in Echo Bay near Sucia Island, Washington. Captain Ron Fugere, who was nearby at the time, recalled seeing what looked like a small ceremony on the yacht's deck.

From a distance, he spotted a woman in a white dress, flower petals being tossed, and an officiant leading what appeared to be a brief exchange of vows.

A second celebration reportedly followed on California's Central Coast, where the couple welcomed around 100 guests to a gathering at Santa Margarita Ranch in San Luis Obispo.

In the 1980s, Kilmer was romantically linked to music icon Cher.

Notable attendees included Joni Mitchell and Stephen Stills. While neither Hannah nor Young officially confirmed their marriage, speculation grew after the actress posted a photo of a white owl to Instagram with the caption, "Someone's watching over us…. Love & only love."

The relationship marked Young's third marriage, while for Hannah — whose past partners included John F. Kennedy Jr. and Jackson Browne in addition to Kilmer — it was her first.

Speaking about their connection during a press tour for "Paradox," a film she directed and in which Young starred, the singer expressed deep gratitude for their partnership, stating:

"We're very lucky to have found each other. I'm eternally thankful for the opportunity to share my life with her, and she feels the same."

A History of High-Profile Romances

While one love left a lasting scar, Kilmer's romantic history included several well-known names from the worlds of film, fashion, and music. Some of these relationships were brief, others spanned years, but all added to the mystique that surrounded his life off-screen.

In the 1980s, Kilmer was romantically linked to music icon Cher after they met at her birthday party. Their connection marked the beginning of a series of high-profile relationships that would follow him throughout the decade. Not long after, he began dating singer Carly Simon, deepening his ties to the music world.

He also developed a relationship with actress Ellen Barkin during this period. Their romance was one of several he reflected on warmly in later years, underscoring the emotional depth of many of his connections, even when they didn't last.

Despite his many relationships, Kilmer only married once. In 1988, he wed actress Joanne Whalley, whom he met while working on the fantasy film "Willow." Their marriage brought two children — daughter Mercedes in 1991 and son Jack in 1995 — before coming to an end in 1996.

Their divorce marked a turning point in Kilmer's personal life, but he remained devoted to fatherhood in the years that followed. After his marriage ended, Kilmer was linked to supermodel Cindy Crawford.

Kilmer's name also came up in connection with Paris Hilton.

Their relationship was followed by a longer-term romance with producer Jaycee Gossett, which lasted for about two years in the late 1990s and early 2000s.

In 2004, Kilmer worked alongside Angelina Jolie on the historical epic "Alexander." Their on-screen partnership sparked speculation about an off-screen connection.

In a more surprising pairing, Kilmer's name also came up in connection with Paris Hilton. Reports surfaced in 2006 that the two had been seen kissing years earlier during the production of "Wonderland," a film in which they both appeared.

In the end, Val Kilmer's life was filled with fame, talent, and notable romances, but one love stood apart. Despite the many women who came and went, he never stopped mourning the one who left the deepest mark — a heartbreak he carried to the very end.