Val Kilmer’s Unexpected Connections to 50 Cent, Bob Dylan, Roy Rogers and … Charles Manson?!

(L-R) Actor Val Kilmer and Rapper 50 Cent arrive at Nokia Theatre L.A. Live on November 22, 2009 in Los Angeles, California
Jon Kopaloff/FilmMagic/Getty Images
Jon Kopaloff/FilmMagic/Getty Images

Val Kilmer has always been known as a renegade. From his friendships to his film roles and beyond, Kilmer’s life and career make a captivating blend of Hollywood fame, personal reinvention — and some truly curious connections.

Read on to learn more about Kilmer’s unexpected connections to some iconic (and infamous!) figures in entertainment, history and pop culture.

The Cowboy Connection: Kilmer and Roy Rogers

THE ROY ROGERS SHOW, Roy Rogers, 1951-1957

Everett Collection

Kilmer comes by his love for portraying Western figures honestly. He grew up on his dad’s San Fernando Valley ranch, where their neighbors were Roy Rogers, the King of the Cowboys, and his wife, Dale. “When Trigger died, they stuffed him — standing on his hind legs — and put him in the living room,” Kilmer told Architectural Digest. “Then their dog Bullet died, and they did the same thing to him. We were always afraid that if Dale died, we’d walk in one day and find her, stuffed and holding a tray, in the kitchen.” The senior Kilmer eventually brought the Rogers property too.

Wild, Horses:  Kilmer and Charles Manson

American criminal and cult leader Charles Manson (1934 - 2017) traveling on a police van to the Santa Monica Courthouse to appear in court for a hearing regarding the murder of music teacher Gary Hinman, Los Angeles, California, 25th June 1970.

Michael Ochs Archives/Getty Images

Rogers and Evans weren’t the Kilmer family’s only famous neighbors. Val told the LA Times that the family also lived “too close for comfort to Charles Manson” when the notorious cult leader and his followers lived on Spahn Ranch. Though the young Kilmer didn’t interact closely with Manson, he learned to ride horses on the ranch.

A Winning Pair: Kilmer and Mare Winningham

HARD PROMISES, Mare Winningham, 1991,

Columbia/courtesy Everett Collection


The hunky Kilmer dated a roster of Hollywood glamour girls, including Cher, Lesley Ann Warren, Angelina Jolie, Daryl Hannah and Ellen Barkin. But his very first girlfriend was St. Elmo’s Fire sweetie Mare Winningham. The pair — who eventually costarred in the primetime after-school special “One Too Many” — dated in high school, where they were both members of the drama club. In his biography, Kilmer said that, in typical teen fashion, he loved her because she was old enough to drive and he wasn’t. In 2022, Winningham married Kilmer’s Top Gun cast-mate Anthony Edwards.

KITT and Caboodle: Kilmer and David Hasselhoff

KNIGHT RIDER, David Hasselhoff, (1985), 1982-86

Universal TV / Courtesy: Everett Collection


Elsewhere star William Daniels famously voiced KITT (“Knight Industries Two Thousand”), the robotic supercar in the 1980s David Hasselhoff starrer Knight Rider. But when the series was briefly revived in 2008, featuring The Hoff as the dad of KITT’s new crimefighting partner, Kilmer voiced Knight Industries Three Thousand. Additional fun fact: Kilmer’s tech whiz Real Genius character also bore the last name Knight.

Does This Make Cents?: Kilmer and 50 Cent

(L-R) Actor Val Kilmer and Rapper 50 Cent arrive at Nokia Theatre L.A. Live on November 22, 2009 in Los Angeles, California

Jon Kopaloff/FilmMagic/Getty Images

Kilmer and his Tombstone costar Michael Biehn took over for Robert De Niro and Dylan McDermott in the 2009 thriller Streets of Blood. And while Kilmer’s own musical taste ran to Bob Dylan, the Beatles, Jimi Hendrix and Led Zeppelin, he became fast friends with another costar: rap icon 50 Cent. The pair bonded over their love of classic cars, and 50 Cent even gifted Kilmer a ’65 Chevy Impala.

A Simple Twist of Fate: Kilmer and Bob Dylan

Musician Bob Dylan performs onstage during the AFI Life Achievement Award: A Tribute to Michael Douglas at Sony Pictures Studios on June 11, 2009 in Culver City, California


Turns out Kilmer’s Dylan fandom went both ways. In an interview with Santa Monica radio station KRCW, Kilmer said that Dylan was a fan of Kilmer’s 1993 western Tombstone. When Kilmer found out, he enlisted a mutual friend to make an introduction. Dylan immediately called the starstruck actor, who invited the folk icon over and was stunned when he accepted.

To his lasting horror, Kilmer refused to talk about Tombstone, or even say the film’s most famous line, “I’m your huckleberry.” To make up for the slight, Kilmer made a tape of him singing Dylan’s “It’s Alright Ma, I’m Only Bleedin’” in his Tombstone character Doc Holliday’s voice, and gave it to the legend.

 

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