When Kris Kristofferson released his debut album in 1970, country music was practically defined by Merle Haggard’s “Okie From Muskogee,” a jingoistic anthem which condemned war protesters, drugs, and “long and shaggy” hair. The song was representative of a genre in an “astonishingly repressive” era, TIME would write a few years later: of cleanly picked guitars, lush orchestrations, and demure lyrics valuing authority and faith.
Then along came Kristofferson: long-haired, antiwar, singing about homelessness and alcoholism and depression and drugs and sex. His tackling of taboo themes startled many in the country establishment: the New York Times called him an “odd man out” in Nashville that year, and TIME labeled him the following year as the “most controversial country songwriter-singer of the day.”
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But Kristofferson’s individualism, contrarianism, and dogged brilliance not only made him a star, but helped kick down genre walls, lighting a path for outlaw country and many other rebels to find a home in both country music’s edges and its mainstream over the past half-century. In a genre often defined by conformity, Kristofferson, who died on Sept. 28 at 88, was proof of another way.
Kristofferson’s resume is perhaps the strangest of any country star’s. He was a Rhodes scholar at Oxford, where he studied the poetry of William Blake, and a Golden Gloves boxer. He served as an army helicopter pilot in Germany and then as a janitor cleaning up after Bob Dylan’s Nashville sessions while he tried to break into the music business. After a few years of pitching his songs around town, other country stars began cautiously recording them in the late 1960s, despite their depictions of racy scenarios and destitution—including Sammi Smith on “Help Me Make It Through the Night,” about a desperate one-night stand, and Ray Price on “For the Good Times,” which Kacey Musgraves later said “might be the saddest song of all time.”
The songs on Kristofferson’s debut album, Kristofferson, delved into even riskier territory, especially given the rightward bent of many country fans. He sang about police brutality and his experience of being arrested; about the state’s mistreatment of Black people and the poor. He mocked the moral hysteria surrounding rock stars like the Rolling Stones. And on his masterpiece “Sunday Mornin’ Comin’ Down,” he sang from the perspective of a dope-smoking vagabond in an existential crisis: “And there’s nothin’ short of dyin’/ Half as lonesome as a sound/ On the sleeping city sidewalk/ Sunday mornin’ comin’ down.” The album received some positive reviews but was a commercial flop.
But the project helped spur other country stars, like Willie Nelson and Waylon Jennings, to embark on their own experimentations and rebellions. This new wing of the genre, soon called outlaw country, was less polished, more prickly and turbulent, more prone to exploring gray areas of morality. These new stars wrote longer songs that broke the genre out of three-minute boxes; they displayed vulnerability and devilish instincts, embracing the dangerous contradictions of a post-Vietnam War, post-1960s America. In 1974, TIME ran a cover story documenting the changes happening in the genre, and quoted Kristofferson as saying: “There’s really more honesty and less bullsh-t in today’s music than ever before.”
After Kristofferson’s star began rising in the early 1970s, thanks in part to him becoming a Hollywood actor, he gave John Prine, another country-ish oddball genius who railed against norms and mindless patriotism, his big break in the business. Kristofferson befriended Muhammad Ali when the boxer was ostracized for his criticisms of the Vietnam War. And he influenced new generations of songwriters by showing them they didn’t have to create within neat genre lines: “His existence told us that we might be able to make some sort of a living from writing songs,” the alternative country legend Steve Earle wrote years later. “He was what I wanted to be when I grew up: a hyper-literate hillbilly.”
In 1985, Kristofferson formed the Highwaymen alongside Nelson, Jennings and Johnny Cash; they gave voice to those on the fringes of society. At a 1992 concert, when Sinead O’Connor was subjected to a torrent of “boos” for her protest against the Catholic Church, Kristofferson came onstage to comfort her and tell her: “Don’t let the bastards get you down.”
And in an industry in which stars are discouraged from voicing political opinions lest they anger potential customers, Kristofferson was fearless in speaking his mind. He criticized the Reagan government in harsh terms on a 1991 talk show, saying: “The fact that we got a one-party system, which is in control of all three branches of our government, and a lapdog media that’s cranking out propaganda for the administration, would make a Nazi blush.” He was a longstanding supporter of the United Farm Workers, playing many benefit shows for them and eventually receiving the Cesar Chavez Legacy Award from the Cesar Chavez Foundation. He said his benefit shows for Palestinian children cost him gigs in Los Angeles: “If that’s the way it has to be, that’s the way it has to be,” he is quoted as saying in a 2009 biography.
Kristofferson battled many demons: He struggled with alcohol addiction and was twice divorced. But he never held himself as a paragon of morality, instead embracing the mess of life, and taking stands where he saw fit. An unfettered approach to songwriting and truth made him a crucial inspiration for many country stars after him, from Travis Tritt to Miranda Lambert to Brandi Carlile, whose supergroup the Highwomen paid homage to Kristofferson’s supergroup. After his death, tributes also poured him from the film industry, including Barbra Streisand, who starred alongside him in 1976’s A Star Is Born.
But fittingly, no one describes Kristofferson better than Kristofferson himself, on the 1971 song “The Pilgrim, Chapter 33,” which he wrote as a tribute to his musical peers:
“He’s a pilgrim and a preacher and a problem when he’s stoned/
He’s a walking contradiction partly truth and partly fiction/
Taking every wrong direction on his lonely way back home.”
