Country Music’s Philosopher King

A Nashville musician once offered Kris Kristofferson some feedback on “Me and Bobby McGee,” the 1971 Janis Joplin smash Kristofferson had written. The musician loved the song’s storytelling about young lovers on the road. But, he asked, “why do you have to put that philosophy in there?”

“That philosophy” was the line “Freedom’s just another word for nothin’ left to lose.” It sounded a little highfalutin, a little abstract, for a humble country tune—and, of course, it ended up becoming one of the most memorable refrains in the 20th-century American songbook.

Kristofferson, who died at age 88 in his Maui home on Saturday, was a guitar-toting stage performer, a ruggedly handsome movie actor, and an outspoken humanitarian and activist. But at base, he was a thinker-poet who pushed country music in existentialist directions. The songs he wrote for himself and others, including Joplin and Johnny Cash, built on the insight that music is philosophy: To write a song is to connect ideas and sound into one flowing whole, to hitch the small to the big, to help everyone see beyond themselves.

Born in Brownsville, Texas, Kristofferson grew up with ambitions of becoming a novelist. As an undergrad at Pomona College, he won a creative-writing contest held by The Atlantic; he went on to earn a Rhodes Scholarship to the University of Oxford. After a stint as a helicopter pilot in the U.S. Army, he turned down an offer to teach English at West Point to instead try to make a living as a songwriter in Nashville. His parents were horrified. “They knew I was going to be a writer,” he said in a 1970 interview with The New York Times Magazine. “But I think they thought a writer was a guy in tweeds with a pipe.”

Making the adjustment from writing for college seminars to writing for beer-soaked saloons took some practice. “His grammar was too perfect,” the songwriter Marijohn Wilkin, who signed him to an early publishing deal, said in a 2003 interview with Nashville Scene. “He had to learn the way people talk.” Kristofferson’s breakthrough hit, “For the Good Times,” performed by Ray Price, was as plainspoken as imaginable. Yet the song’s yearning, calming power arose from what would become his signature technique: placing an intimate moment in cosmic terms. Two lovers are breaking up—but they find comfort in the idea that “this old world will keep on turning.”

He got Cash’s attention with a grand gesture: landing his helicopter on the country star’s lawn with demo tapes in hand. In 1970, Cash made a smash out of one of his songs, “Sunday Mornin’ Comin’ Down,” an impeccable example of Kristofferson finding the profound in the picayune. The first verse sees the narrator joking about drinking beer for dessert, but then his point of view spirals out, from noting the quiet ennui of a hungover morning to reflecting on “the disappearing dreams of yesterday.”

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Another Kristofferson hit of that year, “Help Me Make It Through the Night,” performed by Sammi Smith, was written during a lonely night on an oil platform (he’d had a job helicoptering workers to the rig). Its lyrics were a consummate example of how his emotional-telescoping technique allowed him to create layers of meaning. The words turned a personal experience of solitude into a fantasy of companionship, and in turn offered listeners companionship through their own dark nights of the soul. “Yesterday is dead and gone / And tomorrow’s out of sight,” he sang.

After his early-’70s breakthroughs, Kristofferson became a genuine pop-culture fixture, appearing in big-screen hits (1976’s A Star Is Born) and flops (1980’s Heaven’s Gate). In 1985, he formed the successful “outlaw country” supergroup the Highwaymen, featuring Cash, Willie Nelson, and Waylon Jennings. But as his own music took on more and more explicitly political dimensions over the years, it cost him reach. “For a country singer to be writing songs about Martin Luther King and Mahatma Gandhi and Malcolm X, it’s not hard to see how some of the labels felt that I was unmarketable,” he said in a 2004 Pomona College Magazine interview. After the singer Sinead O’Connor controversially ripped up the pope’s photograph in 1992, protesting the Church’s sex-abuse cover-up, Kristofferson publicly embraced her onstage—a potent gesture for an exemplar of American heartland values to make.

Today, country music—and really any kind of music that prizes depth and authenticity in songwriting—is so in Kristofferson’s debt that his impact can be hard to discern. But in a 2015 speech, Bob Dylan tried to spell out his influence. Speaking in his allusive, meandering style, Dylan suggested that the genre’s onetime unbending fealty to the simple and concrete was revolutionized by Kristofferson’s talent for looking inward and outward. “Oh, they ain’t seen anybody like him,” Dylan said. “You can look at Nashville pre-Kris and post-Kris, because he changed everything.”