Val Kilmer's death at 65 from pneumonia left the world in mourning. Though loved ones were by his side, Kilmer quietly battled loneliness for decades, admitting in his memoir "I'm Your Huckleberry" that he "hadn't had a girlfriend in 20 years" and "felt lonely every day."

Cher
Cher Dimitrios Kambouris/Getty Images/Enstarz

In the early 1980s, Kilmer fell for Cher, whom he described as captivating. "We both loved laughing and went on doing so for well over a year," he wrote. Cher once said, "I was madly in love with Val Kilmer and he left." Despite their split, they remained close.

49th Annual AFI Life Achievement Award Honoring Nicole Kidman -
HOLLYWOOD, CALIFORNIA - APRIL 27: Michelle Pfeiffer attends the 49th Annual AFI Life Achievement Award Honoring Nicole Kidman at Dolby Theatre on April 27, 2024 in Hollywood, California. Kevin Winter/Getty Images for Warner Bros. Discovery

Kilmer and Michelle Pfeiffer formed a deep connection while working together, sharing personal struggles. "The secret pain that Michelle and I shared created an intimacy between us," he wrote.

Ellen Barkin 1994
Ellen Barkin 1994 Getty Images

With Ellen Barkin, Kilmer recalled her laugh and gentle spirit. "I remember her wit, her sultry eyes, but mostly her laugh." Their romance was short-lived but fondly remembered.

Opening Night Of "Monty Python's Spamalot"
NEW YORK - MARCH 17: Singer Carly Simon attends the opening night of "Monty Python's Spamalot" at the Shubert Theatre March 17, 2005 in New York City. Evan Agostini/Getty Images

Meeting Carly Simon after the 'Top Gun' premiere, Kilmer wrote, "We talked all day about everything under the sun." He called her the woman he wanted to be with "for the rest of my life."

FRANCE-FILM-FESTIVAL-CANNES-PHOTOCALL
(From L to R), US actor Val Kilmer, British actress Joanne Whalley, US producer and director George Lucas, US director Ron Howard and British actor Warwick Davis pose during a photocall for the movie "Willow" at the 41th edition of the Cannes Film Festival in Cannes, southern France on May 23, 1988. Photo by AFP) (Photo by -/AFP via Getty Images

Joanne Whalley became Kilmer's only wife. They married in 1988 and had two children, but their union ended in 1996. Whalley cited irreconcilable differences.

Cindy Crawford
Robin Marchant/Getty Images for Cantor Fitzgerald

Following that divorce, Cindy Crawford became a comforting presence. Kilmer said, "I thought I could have died from her love because its delight was simply too much to bear."

Jaycee Gossett and actress Daryl Hannah
Jaycee Gossett and actress Daryl Hannah. Getty Images

Kilmer was later linked to Jaycee Gossett and actress Daryl Hannah. Of Hannah, he wrote, "I cried every single day for half a year."

"Alexander" Premiere In Dublin
DUBLIN - JANUARY 6: Angelina Jolie and Val Kilmer arrive at the Irish Premiere of "Alexander" at the Savoy Cinema on January 6, 2005 in Dublin, Ireland. Julien Behal/Getty Images

He also shared a bond with Angelina Jolie, writing, "I was recused from an icy inferno of solitude by another angel... Angelina."

Tags
Val Kilmer, Celebrity relationships