In Memoriam: Kris Kirstofferson’s Legacy Transcends Categorization

A STAR IS BORN: Kris Kristofferson performing on “The Johnny Cash Show” on Sept. 5, 1976. Photo by Bettmann / Getty Images

It was a surprise.

Kris Kristofferson was going to be inducted into the Country Music Hall of Fame, but he had no idea he was following his Outlaw mentors – Johnny Cash, Willie Nelson and Waylon Jennings – in receiving the format’s pinnacle achievement.

It was August 2004 and he had agreed to announce the final nominees for the CMA Awards, my former employer, on the CBS’ “The Early Show.” During the interview segment, segment host Hannah Storm would break the news, a coveted career milestone caught on camera for millions of viewers.

But there was a glitch. An overeager set designer filled the outdoor plaza with all the country tropes from barn doors to hay bales a la the TV show “Hee-Haw.” It was the sort of stereotypical display that made a publicist flinch and a country icon bristle.

When the segment producer came in for the pre-game, warm up and asked something along the lines of “How far has country music come during your career?” Kristofferson, who never broke stride, said, “Apparently, not far enough…”

The hay bales were dispatched to New Jersey.

Later, in a private car on the way to another media appearance, Kristofferson was genuinely moved. Not by being selected by the Hall of Fame nominating committee and voters, but by the artists who weren’t yet in the Hall including Tom T. Hall and Cowboy Jack Clement.

It was one morning in New York City comin’ down and laying bare the character and soul of a beloved figure in country music: authentic, humble and a fierce champion of the music and artists he revered and causes he believed in who could care less about accolades and hosannahs for himself.

He was everything you wanted your heroes to be. And now he’s gone. Kristofferson, 88, died Sept. 28 in his home in Maui, Hawaii, surrounded by family.

Born Kristoffer Kristofferson in the border town of Brownsville, Texas, on June 22, 1936, he grew up with a military dad and philanthropic mom. He graduated high school in San Mateo, California, in 1954, then attended Pomona College, where he played football and studied writing under Dr. Frederick Sontag, who pushed him to apply for a Rhodes scholarship. At Oxford, he wrote stories and studied the works of William Blake.

Kristofferson could have been a success in any number of disciplines. He was a defensive back, rugby player, bartender, Golden Gloves boxer, forest firefighter and an Army Ranger who flew helicopters. But when he was assigned by the Army to teach literature at West Point, he left the military in 1965 to become a Nashville songwriter.

A skilled and nuanced tunesmith, Kristofferson transformed country music by fearlessly excavating themes that were deeply personal, politically charged and socially progressive. Bob Dylan said in 2015, “You can look at Nashville pre-Kris and post-Kris – because he changed everything.”

It didn’t change immediately. Kristofferson, who was married to his Fran Beer (1961 until 1969), made ends meet flying for a commercial helicopter company and sweeping floors and emptying trash cans at Columbia Recording Studios.

Taking flying under the radar to new heights, he famously landed a helicopter on Johnny Cash’s front lawn to pitch him songs. Cash eventually recorded “Sunday Mornin’ Comin’ Down” (as did Ray Stevens) and in 1970 Kristofferson won CMA Song of the Year.

It was the same year his first solo album was released. It contained several classics including “Sunday Mornin’ Comin’ Down,” “To Beat the Devil,” “Help Me Make It Through the Night,” “Just the Other Side of Nowhere,” “Darby’s Castle,” “Best of All Possible Worlds,” “Blame It on The Stones” and “Me and Bobby McGee,” which became Janis Joplin’s signature hit.

The same year, Kristofferson’s “For the Good Times” was released and became a No. 1 for Ray Price, and Sammi Smith released Kristofferson’s “Help Me Make It Through The Night,” another chart topper.

The real-world gun slinger never looked back

In 1971, Kristofferson launched his acting career. He would go on to win a Golden Globe award for his role in “A Star Is Born.” He appeared in numerous films including “Semi-Tough,” “Songwriter,” “Pat Garrett and Billy the Kid,” “The Sailor Who Fell from Grace with the Sea,” “Convoy,” “Lone Star” and “Blade.”

He toured the world with his band and with Rita Coolidge, his wife from 1973 until 1980. He moved from Nashville to California. And he released seven solo albums between 1972 and 1979.

In 1983, he married Lisa Meyers and two years later, he joined Cash, Jennings and Nelson to form the supergroup now called The Highwaymen releasing three albums over a decade.

The milestone didn’t stop there. In 2003, Kristofferson received the Free Speech Award from the Americana Music Association. Following his induction into the Country Music Hall of Fame in 2004 he received lifetime achievement honors from BMI, the Recording Academy, the Country Music Association and the Academy of Country Music, among many others.

On his 80th birthday in 2016, Kristofferson released The Cedar Creek Sessions, which received a Grammy nomination for best Americana Album six months later. In total, he released 20 albums and won three Grammy awards.

Kristofferson claimed he couldn’t sing, but he could communicate with an audience. Until the pandemic in 2020, he toured constantly – often with Merle Haggard’s band The Strangers – or solo with his Gibson acoustic guitar and a harmonica. His last public performance was April 2023 at the Hollywood Bowl celebrating Nelson’s 90th birthday.

His Pollstar Boxoffice Reports date back to 1981 with a total gross of $21.4 million and 604,027 tickets sold on 348 shows, though he clearly played far more. His best box-office results came as part of the aforementioned Highwaymen (with Cash, Jennings and Nelson), which included 34 shows between 1990 and 1995 with a total gross: $5,626,558 (about $12.3 million in 2024 dollars) and 276,873 tickets.

Kristofferson is survived by his wife, Lisa; eight children, Tracy, Kris Jr., Casey, Jesse, Jody, John, Kelly, and Blake; and seven grandchildren.

Looking back on that August morning in 2004, Kristofferson was doing an interview from the car with a reporter from The Tennessean that seems as meaningful today as it did then. He said, “I wanted country music to be as proud of me as I was of being in country music. Over the years, I guess it happened.”