The Unbroken Circle: Kris Kristofferson’s Sorrowful Inspiration

The Unbroken Circle is a recurring feature where I discuss classic country songs, though for this particular feature, I found it easier to write a collective essay about Kris Kristofferson and a few key cuts related to this piece.

With the somewhat recent news of Kris Kristofferson’s retirement, I think about the inevitable question that comes with it: How will we judge his entire career? How will we remember him?

The answer, of course, is fairly simple. He’s an accomplished songwriter who’s penned a slew of master-works and completely changed how songs in Nashville could be written. He’s a part of the Country Music Hall of Fame, he’s an accomplished movie star, and he made such shocking and controversial political statements in his time … for freedom, justice, human rights and other, you know, divisive ideals of yesterday and today. It sounds easy, and is, to group together the numerous accomplishments.

Granted, I obviously don’t know him, but there’s a part of me that simultaneously can’t help but feel like that doesn’t do him enough justice to leave at that and that he’d just hate that sort of basic summation. A lot of words were in Kristofferson’s dictionary – if anything, Rodney Crowell said it best when he remarked, in reference to “Sunday Morning Coming Down,” that, “Hey, all those words are in the dictionary, but nobody else before Kris knew what damn order they came in” – “easy” just wasn’t one of them.

But this isn’t the part where I shift over to a backstory filled with trials and tribulations of how he got to where he did; not yet, that is. I know, I know, it’s a story about a country music artist – to have it not be about that just doesn’t make sense. It’s kind of dangerous to assume that profound suffering is necessary for great art, though, you know? I don’t think Kristofferson ever received that memo. In truth, he was the – oh, let’s keep it thematic – textbook example of privilege. He was a Golden Gloves boxer, a college football player, a published writer, a competitive wrestler, an Army Ranger and a Rhodes Scholar … you know, among other things. It was the sort of sophisticated life his traditional, well-to-do (and strict) family wanted for him.

If anything, though, Kristofferson sought pleasure in the desperation and achievement, to be the best because he’d earned it, not because it was handed to him. One of his biggest delights as a youth came from a summer job, in which the superintendent of his construction crew told him he was the best man on the job. Competition fueled Kristofferson’s fire. I sound like I’m prepping a story that’s comprised of myth, but really, this could have had a much darker ending that wouldn’t have received nearly as much attention.

And there’s also an irony, really, in how his parents’ teachings both shaped him and pushed him away from his upbringing. From his father, Henry, a major general who served in World War II and Korea and later became a commercial airlines manager, he learned what true accomplishment meant – how to ignite that fire, in a sense. From his mother, Mary Ann, he learned from her lessons of social justice that would shape his yet-to-be written poetry. They were proud of the son who entered the prestigious Pomona College (his mother’s alma mater), even if it was to play rugby and football, rather than engage in academics. Well, that’s not entirely true. Along with joining the Reserve Officers’ Training Corps (a way of doing dear ol’ dad proud), Kristofferson graduated Phi Beta Kappa in English literature, before going on to Oxford, England, as a Rhodes Scholar to spend even more time with his beloved Romantic poets.

While in London, Kristofferson flirted with many creative ventures, including a novel and a short recording stint for the ill-fated Top Rank Records as “Kris Carson.” His main hero wasn’t of a musical variety, though he did grow up idolizing Hank Williams and other country icons as a child. Instead, it was William Blake, a poet whose main teaching was about how anyone who refuses spiritual acts in favor of worldly desires and the need for natural bread will be pursued by sorrow and desperation through life and by shame and confusion for eternity. This made Kristofferson ponder whether he was put on this Earth to write, and that if he refused, well, you know.

That thought slumbered as he earned his master’s degree, went back home to California, married his high school sweetheart, joined the army, and learned to fly helicopters. He still loved ol’ Hank, but he knew his parents didn’t think much of country music. Besides, he was more interested in being the next Hemingway anyway.

Bob Dylan

Bob Dylan convinced Kris Kristofferson that there was a way to combine the best of all possible worlds in music and poetry. Credit: Sony Music

Indeed, it wasn’t really country music that convinced him to take a different path – not initially, that is. It came via folk singer Bob Dylan, whose way with words convinced Kristofferson that there was a way to combine the best of all possible worlds in poetry and music. It presented a crossroads in his life only further amplified when upon trying to volunteer for Vietnam, he was rejected, because he was assigned to teach literature at the Academy, at West Point. The thought of what he’d have to do – teach to cadets formed in a semi-rectangle around him all while turning in lesson plans 24 hours before each class – sounded like hell to him.

Before he started, an impromptu trip to Nashville for a few days in 1965 helped him better understand his childhood dream. He was in a town that didn’t know the meaning of “lesson plans.” Songwriter Marijohn Wilkin, a cousin of Kristofferson’s platoon leader, agreed to show him around. She introduced him to Cowboy Jack Clement, who amplified the rambling spirit within Kristofferson he yearned to unleash. He took Kristofferson behind the scenes at the Grand Ole Opry, in which he introduced him to Johnny Cash, who Kristofferson recalls then was, “skinny as a snake” and “was going to end up like Hank Williams.”

Desperation. Cash had it, Kristofferson craved it, and he resigned his West Point position to move to Nashville and become a songwriter. A dream is just that, though, and Kristofferson initially started as a bartender, then as a janitor for Columbia Records, slipping demo tapes and lyric sheets to artists passing through; even Cash. He struggled, though. He divorced from his wife and was disowned by his family, seeing as how his parents couldn’t fathom anyone over the age of 15 liking country music (“rubbish” is how they put it). Clement told Cash about the letter, to which Cash came up to Kristofferson and said, “It’s always good to get a letter from home, isn’t it, Kris?” He was impressed with the songwriter’s gumption.

Again, we know how it ends, but that time may have marked Kristofferson’s darkest point yet. He had figured total immersion into Nashville’s hazy wildlife was the only way to understand its culture, its artists, and its music. Even he began to feel the pressure. Success came in spurts – like when Dave Dudley took “Vietnam Blues” to the top 20 in 1966 and when Billy Walker recorded “From the Bottle to the Bottom,” which impressed another songwriter, Tom T. Hall – but Kristofferson found success from the unlikeliest of places: himself. Publisher Fred Foster signed him on the basis that he’d bring him four songs worth hearing. One could just be a fluke, so, I guess, could two. But four was his magic number of determining whether or not an artist was truly a writer. Those four songs ended up being “Jody and the Kid,” “To Beat the Devil,” “Duvalier’s Dream,” “Best of All Possible Worlds,” all of which would make a self-titled debut album Kristofferson didn’t want to make. “I sing he like a fucking frog,” he said, to which Foster countered with, “yes, but one that can communicate.”

What should have marked a new chapter was instead just a reminder of the things Kristofferson had lost to get there. It’s from that melancholy that some of his best ever work came about.

Indeed, his biggest hits for others carried that balance of hope and despair. In a bachelor’s department one Sunday morning, frustrated by how was there nothing to do until the bars opened up, he wrote the words that communicated his complex decisions made thus far. They formed “Sunday Morning Coming Down” a song that became just as autobiographical for the artist who recorded it as it was for the person who wrote it.

Johnny Cash

Johnny Cash had a desperation that Kris Kristofferson wanted – needed. Credit: Hulton Archives, Getty Images

Of course, it’d apparently take more than a letter from home for Johnny Cash to take any further notice of Kristofferson. Those demo tapes and lyric sheets mentioned earlier that he slipped to artists? They made their way to Cash, only he’d throw them in the same pile as the others he’d received from aspiring artists, which would eventually make its way to Old Hickory Lake. So Kristofferson took a tape with him and piloted a National Guard helicopter onto Cash’s front lawn, convinced that he would like his music if given a chance. Like so many other parts of this story, it could have ended really badly, and did not, as the story famously goes, include Kristofferson stepping out with a beer in one hand and a tape in the other. It’d be impossible to fly like that.

Safe to say that Cash liked “Sunday Morning Coming Down,” and he recorded it live on his late ‘60s television show. The network objected to the line, “wishing, Lord, that I was stoned,” and insisted a change to, “wishing, Lord, that I was home.” Kristofferson was in the audience, and if you think Cash actually went through with the change, you haven’t been paying attention.

That friendship is echoed in another story, in which Kristofferson, then still a janitor, became friends with Larry Gatlin, an aspiring gospel singer who shared a kindred spirit with someone who craved success … on his own terms, that is. There’s darkness in that story, too, as while Gatlin kept his faith, he also struggled with drug addictions and alcoholism. He regularly attended the Evangel Temple just outside of Nashville, where the pastor was Jimmie Rodgers Snow, son of Hank Snow who owed his namesake to Jimmie Rodgers, his father’s idol. Kristofferson found his way to the same church one night, too, after driving through the night back to Nashville from a concert with Connie Smith, who convinced him to go. He was an outcast to nearly everyone but himself, as this story shows, and given that he wasn’t raised in the evangelical tradition, it’s a miracle he walked down when the preacher asked for those who needed to be saved. Same concept, I guess. Simply put, the experience had a profound impact on him, which prompted him to write “Why Me,” his highest-charting solo hit, and featuring Gatlin singing harmony.

Janis joplin

Janis Joplin died not long after recording “Me and Bobby McGee,” adding a deeper sadness to it for Kris Kristofferson. Credit: David Gahr, Getty Images

The idea for another classic, “Me and Bobby McGee,” first recorded by Roger Miller and made famous by Janis Joplin, started much more innocently. It was a phrase Foster used when he met Boudleaux Bryant’s new secretary, Barbara McKee, who everyone just called Bobbie. He simply told Kristofferson to write a song called “Me and Bobby McKee,” when the songwriter told him he was fresh out of ideas (I know, right?). He obviously misheard the intended title. He thought of the film La Strada, in which a man abandons his significant other after a long journey, leaving him, in the end scene, to get drunk at a bar, look up at the stars, and weep. He wanted to capture that same feeling of something that was good for a long time, but, like all things, eventually ends. Foster shared half of the writing credit for its title, and the rhythm was inspired by a Mickey Newbury song, “Why You Been Gone So Long.”

At this point, too, it’s worth noting the impact Kristofferson’s lyrical perspective was carrying in Nashville for the time. He focused more on being sensual and direct on something like “Help Me Make It Through the Night,” made famous by Sammi Smith, rather than skirting around and sanitizing the core. This came at a time when country music, if only for a moment, was attractive to an outside audience. Crossover hits of the ‘70s in “King of the Road,” “Harper Valley P.T.A.” and “A Boy Named Sue” all amassed huge sales and attention for the industry, and with Kristofferson’s own material standing alongside efforts from the aforementioned Tom T. Hall and Mickey Newbury, country music was getting dadgum sophisticated. He should have been on top of the world, yet regret lingered in the back of his mind. He reconciled with his mother, but not the fact that, despite his successes, he still wasn’t living up to his parents’ ideals. In truth, it was selfishness and irresponsibility that fueled his success, and that grand allure of living like a country star suddenly came with the addendum that maybe the payoff wasn’t worth the struggle to get there. Stories about him usually capture that burst of creativity that led to his aforementioned biggest (and, arguably, best) songs. But those dark complexities swirled around him long afterwards. On 1974’s Spooky Lady Sideshow, for instance, a concept album about reaching your peak and wondering what’s next, opener “Same Old Song” includes the line, “finding out the bottom ain’t so different from the top/Just a few more friends you’ll be losin’ when you drop,” and the rest of the collection is just as dark and cynical.

Maybe that’s why I was inspired to write this after a weekend viewing of A Star is Born for the first time, a wildly unhinged portrayal of hitting rock bottom that stars Kristofferson alongside Barbara Streisand and provides the zaniest version of its many adaptations through time (hey, it was the ‘70s). It’s also one that mirrors the person Kristofferson became in real life, albeit to a much more extreme degree. He became a writer, an actor, a star, a sex symbol … someone who came by things easy – again, too easy – and wanted to live up to his responsibilities as a human being as he became more outspoken (or, as the industry calls it, irrelevant). William Blake’s main lesson never quite left him, it just altered its form. Another irony: Despite mostly being known for his work in the ‘70s, Kristofferson’s legacy is mainly secure, almost to the point of not being able to accurately capture the walking contradiction he was then. Maybe it’s because the main takeaway is this: The best-known songwriters are empathetic human beings who write empathetic things about other human beings. Kristofferson wrote about himself probably even more than he knew, but to find the relatable aspects of the contradictions that shape us – both as humans and music lovers – that’s easy, and that’s timeless. Frogs that can communicate do tend to have that quality.

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