Kris Kristofferson was a man to whom myth attached easily.
Did he once take control of a National Guard helicopter so he could land it at Johnny Cash’s house to present him with some songs to consider recording? (He sure did, though Johnny apparently wasn’t home.) Did he not know that Janis Joplin, whom he’d been dating, had recorded his song “Me and Bobby McGee” just a few days before her death? (He didn’t; the track, released posthumously, became her lone No. 1 hit.) Did he once confront Toby Keith, country music’s jingoist in chief, about his performative bluster and ask him, “Have you ever taken another man’s life and then cashed the check your country gave you for doing it? No, you have not.” (Depends whose account you believe.)
Beginning in the mid-1960s, when he arrived in Nashville as an aspiring songwriter, Kristofferson, who died Saturday at 88, evolved into something of a communal conscience for the town, and the country music business, while also helping to usher it into conversation with the rest of popular music.
He was best known as a songwriter, with compositions that bridged folky earthiness with a jolt of literary flair. When sung by some of the biggest country stars of the era — Cash, Ray Price, Roger Miller, Ray Stevens, Bobby Bare — they inexorably moved the genre away from polished and poised singers in sports coats toward thornier territory closer to the folk revival of the 1960s.
The protagonists of Kristofferson’s best songs were downtrodden victims of their own poor decisions — “Sunday Mornin’ Comin’ Down,” the best-known version of which was sung by Cash, finds the singer struggling to find “my cleanest dirty shirt” the morning after a Saturday night bender. “Once More With Feeling,” written with Shel Silverstein and sung by Jerry Lee Lewis, tells the story of a relationship that’s run out of gas through the pleas of a man desperate to be deceived, even for a moment: “Darling, make believe you’re making me/Believe each word you say.”
“Me and Bobby McGee” — initially recorded by Miller, but rendered indelible by Joplin — was the tale of two drifters who drift away from each other, anchored in the oft-repeated secular proverb, “Freedom is just another word for nothing left to lose.”
All of Kristofferson’s aura could obscure the fact that as a recording musician, he was popular but not astronomically so. His only solo albums to reach the Top 10 on the country chart were his first few, from the early 1970s. He had exactly one solo No. 1 country hit: “Why Me,” which filtered his trademark desperation in a gospel mode.
Most of the later part of his career was defined by acting more than music. Kristofferson, lean and handsome and with the cocksureness of a onetime athlete, was quickly upstreamed into movie stardom. Onscreen and onstage, he had the air of someone who knew much more than he was willing to tell, which made him a natural at playing troubled heartthrobs (“A Star Is Born”) and grizzled mentors (“Blade”).
And yet he still retained a certain power and gravity in country music, where his wise elder status carried well into the 1980s and beyond. He was a member of the Highwaymen — alongside Cash, Willie Nelson and Waylon Jennings. (Of the four, Kristofferson had been by far the least successful as a recording artist.) In an interesting twist, the former outlaws had become institutional icons, while retaining their ragged charm. Their first two albums, especially, were generation-threading love letters that slyly linked the rebels to the veterans, underscoring how blurry those lines had always been.
That Kristofferson would be one of the voices entrusted with that history was never a guarantee. His earliest encounters with Nashville’s old guard weren’t terribly encouraging. That tension was epitomized at the 1970 Country Music Association Awards, where he won song of the year for “Sunday Mornin’ Comin’ Down.”
In a room full of Nashville’s grinning old guard, Kristofferson, in a black suede jacket, and with shoulder-length hair dancing around his face, came down the aisle part-saunter, part-stumble. He received the award from Roy Clark, the “Hee Haw” host and an ultimate Nashville insider, who nudged a reluctant Kristofferson to the microphone to make his speech.
Did he ever once look at the camera? (He did not.) Was he stoned? (Many suspected yes, but he later said he was just nervous.) Did he walk right back into the crowd as if running from the spotlight? (He certainly did.)
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