Highwayman: Remembering Kris Kristofferson
The film and music legend was 88
Kris Kristofferson, who passed away Saturday, September 28 at the age of 88, was one of those artists whose talent defied any preconceived boundaries.
He began his professional career as a songwriter, and if that’s all he had done throughout the remainder of his life, it would have marked him as an immeasurable talent all on its own. Nevertheless it quickly became apparent he wasn’t merely content to compose songs for others — although given the fact that he was one of the most covered writers of his era, he easily excelled. Instead, he transformed the emotion imbedded in his hard-luck stories into a personal mantra that was never immune to life’s difficult realities or misguided by an attempt to mask the pain and disappointment that can come when an initial prospect looks promising, but doesn’t go as well as planned.
Songs such as “Sunday Mornin’ Coming Down,” “Help Me Make It Through the Night” and “Born to Die Alone” captured that sense of despair and desperation left behind after dreams which were once imagined the night crash to their conclusion the morning after.
Kristofferson first rose to prominence when Ray Price covered his seminal song “For the Good Times” and Janis Joplin, with whom he was rumored to have had a romance, recorded a song that would become a classic, “Me and Bobby McGee.” A travel log of sorts, it was ostensively about a road trip taken in tandem by a pair of lovestruck drifters. It begins well enough, but eventually ends up on the rocks when the namesake character deserts her lover.
VIDEO: The Highwaymen perform “Me and Bobby McGee” at Nassau Coliseum
Like John Prine, an artist with whom he can most readily be compared in terms of attitude and approach, Kristofferson began his career in humble happenstances. Prine was a singing mailman while Kristofferson took his first step towards making music as a part-time janitor sweeping floors at Columbia Studios on Music Row in Nashville. However he was groomed for success in other realms well before that. An athlete of exceptional prowess, he made his mark in college as a Golden Gloves boxer and by playing team sports in both rugby and football. He wasn’t simply a jock however. He received a master’s degree in English Literature from Merton College at the University of Oxford in England where he famously became a Rhodes Scholar. Yet, because he was the son of an Air Force general, he felt obligated to enlist in the Army, flying helicopters before being promoted to the rank of captain. He was given an appointment to teach at the U.S. Military Academy at West Point, but turned it down in order to pursue songwriting.
It was while working as a janitor at Columbia Studios that he happened to meet June Carter Cash, whereupon he asked her to give her husband Johnny one of his tapes. When he didn’t hear back, legend has it that he landed a helicopter on Cash’s lawn to personally hand The Man in Black his tape. The story may have been exaggerated as an urban myth, but the supposed incident was well in keeping with Kristofferson’s oversized persona.
Although his eponymous debut album was a commercial failure until its rerelease as Me & Bobby McGee, the three that followed — The Silver Tongued Devil and I (which boasted one of his best-known early standards, “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)”), Border Lord and Jesus Was a Capricorn — established him as an artist to be reckoned with.
After subsequently connecting with singer Rita Coolidge, both personally and professionally, his singing career got a further boost courtesy of the initial album the pair recorded together, aptly titled Full Moon.
Nevertheless, while his success as as a songwriter continued to grow, his own stock as a recording artist began to flounder. Still he could bank on other advantages. Given his rugged good looks, he easily made a transition to films. He made his onscreen debut in Dennis Hopper’s 1971 low-budget effort The Last Movie, and then went on to score box office success to a great degree courtesy of Pat Garrett and Billy the Kid, Alice Doesn’t Live Here Anymore, Convoy, Heaven’s Gate, Lone Star and the Blade trilogy. However, he’s best remembered for the torrid love scenes he shared with co-star Barbra Streisand in the box office smash A Star Is Born, which earned him a Golden Globe Award for Best Actor in the process.
VIDEO: Kris Kristofferson talks about dating Barbra Streisand on Letterman
Kristofferson’s music career was rekindled to a great degree when he joined the supergroup The Highwaymen alongside such venerable colleagues and contemporaries as Willie Nelson, Johnny Cash and Waylon Jennings. The group put out three studio albums between 1985 and 1995 — their eponymous debut, Highwaymen 2 and The Road Goes On Forever — in addition to several live offerings and a compilation titled The Essential Highwaymen. As the forerunners of the outlaw country movement, those recordings served each member with good standing. Sadly, Jennings died in 2002 and Cash died a year later, leaving Nelson as the group’s sole survivor.
“I think I was different from the other guys in that I came in it as a fan of all of them,” Kristofferson told the Associated Press in 2005. “I had a respect for them when I was still in the Army. When I went to Nashville, they were like major heroes of mine because they were people who took the music seriously. To be not only recorded by them but to be friends with them and to work side by side was just a little unreal. It was like seeing your face on Mount Rushmore.”
Nelson returned the complement, telling those assembled for Kristofferson’s 2009 BMI Award ceremony, “There’s no better songwriter alive than Kris Kristofferson. Everything he writes is a standard and we’re all just going to have to live with that.”
Notably, after Kristofferson announced his retirement from performing, his final appearance took place in 2021 when he took part in Nelson’s 90th birthday celebration at the Hollywood Bowl in Los Angeles. He sang a duet with Rosanne Cash on “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” a song that became a staple in Nelson’s live setlist.
This reporter caught his performance at Merlefest in 2018 when he was backed by The Strangers (Merle Haggard’s original backing band, as well as Haggard’s son, Ben.) Sadly, Kristofferson didn’t appear to be in fighting form. He looked tired and haggard, and his voice clearly lacked the expressive energy it once had. Nevertheless, it was a thrill to catch a legend in concert especially since the setting provided such a rare opportunity.
VIDEO: Kris Kristofferson “Loving Her Was Easier (Than Anything I’ll Ever Do)”
As befits a legend, Kristofferson could claim any number of kudos throughout his career, ensuring a lasting legacy in the annals of essential Americana. His honors included multiple awards from the Academy of Country Music and the Country Music Association, as well as the Americana Music Association, a Grammy Award, the aforementioned Golden Globe Award, an Academy Award nomination and numerous other music award nominations also. In addition, he received a long-overdue induction into the Country Music Hall of Fame in 2004.
When he died at his home in Maui from a heretofore undisclosed ailment, he left behind a body of work that remains unrivaled, not only in the annals of country music, but the whole of popular music as well. A remarkable presence in every regard, his efforts still loom large as a true American icon.
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there is a fine Steve goodman documentary floating around YouTube with Kris, Prine, Marty Stuart and others.
Erally fine.
He tells the whole3 story of discovering Prine.
very nice.