Kris Kristofferson, a man who seemingly could have been successful at just about anything he tried, turned his cathedral-like mind and working man’s heart to the arts. He was a scholar, a soldier, a pilot, an athlete, an actor, and, as most people know, one of America’s greatest songwriters. He was a member of several exclusive societies, including Oxford University’s Rhodes Scholars and country music’s epochal Outlaws, as well as a free thinker and activist across decades. On Saturday, that exceptional life came to an end when Kristofferson died at home in Maui, HI at age 88.
For music lovers, Kristofferson was a profound wordsmith whose literary understanding and flair never overshadowed his ability to reach just about everyone with clear, insightful storytelling and observation. In “Me And Bobby McGee,” he minted the timeless wisdom that “Freedom’s just another word for nothing left to lose.” In “Sunday Morning Comin’ Down,” Kristofferson made us wince with recognition when his narrator reached for “his cleanest dirty shirt.” And in “The Pilgrim, Chapter 33,” the writer evoked a whole throughline of literature connecting his friends Johnny Cash and Dennis Hopper to Odysseus himself with the immortal lines, “He's a walking contradiction, partly truth and partly fiction/Takin' every wrong direction on his lonely way back home.”
Kristofferson’s songs topped the country and pop charts more often through interpretations by other artists than himself, but that didn’t obscure his impact or his fame. For years, writers of country and folk songs from the humble to the famous have cited the Texas native as an inspiration on par with Bob Dylan, Leonard Cohen, and Hank Williams. Steve Earle told NPR that Kristofferson "raised the bar single-handedly in country music lyrically to a place that writers are still aspiring to, and I still aspire to, to this day."
In June of 1936, Kristoffer Kristofferson was born into a high achieving family in Brownsville, TX, the southernmost tip of the state on the Mexican border and the Gulf Coast. His father was a hero of WWII aviation and an Air Force Major General who urged his eldest son to pursue the military. Kris did so, but only after forming literary ambitions and launching them by having essays published in the Atlantic Monthly while attending Pomona College in California. He continued his studies at Oxford University, studying Shakespeare and William Blake, earning a Bachelor’s of Philosophy in English literature in 1960. While there, he began performing his songs, but the English music scene wasn’t a match for him.
Kristofferson married back in California and joined the Army, becoming a helicopter pilot and achieving the rank of Captain. While stationed in Germany, he continued his songwriting and got a tip that he should reach out to Marijohn Wilkin, writer of “Long Black Veil” and a Nashville publisher. With her encouragement after a scouting visit to Music City, Kris made the most momentous decisions of his life - to leave the Army and give songwriting his full attention. On his first day in town, he met Cowboy Jack Clement, exactly the kind of dissident record and song man he needed to know in a fast-changing city. And with that, in 1965, the mythology of Kris Kristofferson truly begins.
Influential figures like Clement and Tom T. Hall recognized Kristofferson’s talents, but there was no quick path to success. Here’s where we hear about the handsome, accomplished man taking a job sweeping floors and emptying ashtrays at Columbia Records on Music Row, where he witnessed sessions by Bob Dylan and Johnny Cash, among others. He also took weeks away to make money flying helicopters to and from oil rigs in the Gulf of Mexico. For four scuffling years, his family let him know unequivocally that he was a grave disappointment to them. And then things began to break his way.
Trucker country star Dave Dudley recorded his surprisingly pro-war song “Vietnam Blues” in 1966. Billy Walker cut “From The Bottom To The Bottle,” a profile of “a down and outer waking up alone”. Both reached the Top 20. Then Roger Miller took up a song inspired by producer/publisher Fred Foster but penned by Kristofferson, the romantic road song “Me and Bobby McGee,” which neared the top 10 in 1969. A Gordon Lightfoot version went No. 1 in Canada. Then, on the day Janis Joplin died, Kristofferson was surprised to learn that the San Francisco blues rocker had recorded it. The posthumous single was a smash that wound up in the top 150 of Rolling Stone’s 500 Greatest Songs of All Time.
An even stranger sequence of events helped “Sunday Morning Comin’ Down” find its way to the pantheon. It was first cut by, of all people, Ray Stevens (of novelty song “The Streak”) in 1969, but fortunately Johnny Cash adopted the song for his TV show from the Ryman. A single of that live performance reached No. 1 on the country charts and was awarded Song of the Year by the CMA for 1970.
By then, Kristofferson was a respected writer in Nashville, and Foster’s Monument Records took a chance on him as an artist. His debut album, simply titled Kristofferson, included his big radio hits as well as his exceptional songs “Help Me Make It Through The Night” and “Darby’s Castle,” yet its sales were modest. A re-issue titled Me And Bobby McGee did better, reaching the country Top 10 and going Gold.
Following a bit part in a 1970 motion picture, Kristofferson made his debut as a leading actor in 1972’s Cisco Pike opposite Gene Hackman. It fared better with time than during its first run, but in the coming years, Kristofferson appeared in scores of wildly diverse film and television productions, including with directors Sam Peckinpah, Martin Scorsese, and John Sayles. His greatest film triumph and star turn came with Barbara Streissand in the 1976 box office smash A Star Is Born, for which he won the Golden Globe Award for Best Actor In A Musical.
While the movies helped Kristofferson achieve household name status, his songwriting was the fuel that confirmed him a musical legend in the years to come. Even Bob Dylan said that Nashville’s story has pre-Kris and post-Kris eras. “He changed everything,” says Dylan in the family’s official biography. While he struggled with depression as the 70s gave way to the 80s, he found stability after meeting and marrying Lisa Meyers, with whom he had five children and who was at his side when he died.
In 1985, Kris was back in the public eye in the best possible way as part of an outlaw supergroup that would become known as The Highwaymen, alongside Cash, Willie Nelson and Waylon Jennings. Over a decade they released three albums, toured as a star country music package, and starred in a western movie together.
Kris’s own solo recording career languished, but in a surprising turn, rock and pop producer Don Was helped the artist find himself again in the studio, playing a similar role to Rick Rubin’s contributions to Cash’s late career comeback. Was and Kristofferson made four well-received albums together between 1995 and 2013. His final album The Cedar Creek Sessions, his 22nd LP, came out in 2016 and earned a Grammy nomination for Best Americana Album.
Many accolades came Kristofferson’s way in his later years, including the Americana Free Speech Award (2003), induction into the Country Music Hall of Fame (2004), a Grammy Lifetime Achievement Award (2014), and a CMA Lifetime Achievement Award (2019).
Kristofferson told The Fader in 2009 about sticking to his vision when it seemed most improbable: “When I went to Nashville, I was a Captain in the Army and I’d been to Oxford, and I’d raised a lot of expectations, in my parents and some other people, and those expectations didn’t include being a songwriter or a janitor in Nashville. I feel really lucky that I stuck with it, because it’s what I love to do.”
