What Would Kris Kristofferson Do?

Remembering country music's Renaissance man

Welcome music lovers!

For this edition of ‘Listening Sessions,’ I wanted to put down some thoughts on Kris Kristofferson, who passed away on September 28 at the age of 88. To me, Kristofferson represents the ideal of the country-music singer-songwriter, the rebel of fierce principle, able to hold his own at a bar but also possessed of a deeply poetic streak. In a way, he embodied the Wyatt Earp of John Ford’s My Darling Clementine. While I am not as familiar with the entirety of Kristofferson’s discography as others, I do feel his debut album from 1970 is a profound artistic statement and it forms the focus of my essay.

There have been many fine tributes to Kris Kristofferson on Substack, including Dan Epstein, Michael Elliot and the good folks behind Don’t Rock the Inbox. I hope I have added something extra to these pieces.

Until next time, may good listening be with you all!

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In a response to a tweet obliquely asking for comment on the legacy of Kris Kristofferson, Tyler Mahan Coe, creator of the labyrinthine country-music podcast Cocaine & Rhinestones, had this to say: “Trying to use words to sum up the life of Kris Kristofferson feels abjectly insane. He said it all. The best we can do is listen.” And yet, some assemblage of them are required, whether through the obligatory newspaper obituary, a listing of his most notable performances or an essay to try to make sense, or perhaps more accurately I think, to attempt to explain why the news of his passing on September 28 is so affecting.

When I first saw a tweet that announced that Kris Kristofferson had died, I gasped as one often does when someone famous passes away. These are individuals whom we don’t know but there are a select few that actually know us more than just about anyone; family, friends and other loved ones included. This is no surprise. Someone writes a song or a book or a movie that reaches across the divide to speak directly to someone whose life and the circumstances surrounding it had absolutely nothing to do with its creation. This kind of cosmic connection is not to suggest that to feel it is to be like Travis Bickle (Robert De Niro) in Taxi Driver who is stymied when the presidential campaign worker Betsy (Cybill Shepherd) characterizes him as “a walking contradiction, partly truth and partly fiction,” and after she reveals that she was quoting the words of Kris Kristofferson, Bickle confesses he has no idea who he is.

Kristofferson embodied the contradictions that are a fact of life. To encapsulate his life in one sentence reveals not only how much he packed into 88 years of living but that within us all lie endless possibilities of where the journey of life can take us.

Of all the things that he did and achieved, the one I keep returning to is that Kristofferson had been a Rhodes Scholar. He studied English literature with a focus on the romantic poet William Blake at Oxford’s Merton College from 1958 to 1960, earning a Bachelor of Philosophy in English literature. Of course, the idea that he had once been a clean-cut prepster—in addition to his academic pursuits, Kristofferson played rugby and boxed—seems deeply at odds with the image he would cut at the dawn of the seventies in Nashville. But, it also spoke to the multitudes within the man, a depth that made him a paragon of fidelity to principle and integrity; the kind of person to buck the crowd and encourage Sinead O’Connor to “don’t let the bastards get you down” or, apocryphally, cut someone like Toby Keith down to size.

Comparisons to Johnny Cash are inevitable, not only because of the important role he played in Kristofferson’s musical career but also in how both represented an ideal in how to live. In Cash’s case, it was that one could be a rebel while also being devoutly and publicly religious (his life illustrates the day-to-day struggle to try to adhere to the Christian life). Kristofferson showed how one could be a rebel while cultivating an intellectual life—put simply, he showed it could be cool to be smart.

In 1965, he shunned an offer to teach English at West Point to see if he could hack it in Nashville. He put the stakes in the choice he made this way in Ken Burns’ documentary on country music: “I love William Blake…. William Blake said, “If he who is organized by the divine for spiritual communion, refuse and bury his talent in the earth, even though he should want natural bread, shame and confusion of face will pursue him throughout life to eternity. He’s telling you that you’ll be miserable if you don’t do what you’re supposed to do.”

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He took a job as a janitor at Columbia Records’ studio in Nashville, emptying the ashtrays while Bob Dylan recorded Blonde on Blonde and holding the bongos while Kenneth Buttrey played them on Dylan’s ‘Lay Lady Lay.’ He went to extraordinary heights to get Cash’s attention, including flying a helicopter and landing near the singer’s home to hand him a demo tape (Cash wasn’t there at the time and, despite the more exaggerated versions of the story, Kristofferson did not emerge from the chopper holding a beer in one of his hands).

He also went the more conventional route, pitching his songs on Music Row and here, he began to get traction and become part—many would say he became the leader—of a group of songwriters and performers who were writing sophisticated and personal songs that moved country music away from the polish of the Nashville Sound. In addition to Kristofferson, there were Townes Van Zandt, John Stewart, Jerry Reed, Mickey Newbury and Mac Davis, to name a few, becoming like, before them, Willie Nelson, Bill Anderson, Don Gibson, Hank Cochran and Roger Miller among others, singer-songwriters whose songs were expected to be covered frequently.

Miller was among the first to mine Kristofferson’s growing songbook, recording three of his songs for his 1969 album Roger Miller. Most notable historically was the first appearance on record of ‘Me and Bobby McGee’ but more notable musically was a lightly adorned interpretation of ‘Darby’s Castle.’

Miller thrived on the extremes of the musical spectrum. His maniacal side, as heard on something like ‘Dang Me,’ was balanced by the directness of something like ‘Husbands and Wives.’ ‘Darby’s Castle’ brought the latter out in Miller. He narrates the tragedy of Cecil Darby, who labours away to build a beautiful home for his wife, Helen Darby, and to lavish her with things until one night, he sees her with another man in their marital bed.

Setting aside Miller’s performance, and it is a remarkable one, ‘Darby’s Castle’ has Kristofferson treating his tale like a short story, using observations to imply things that in a lesser songwriter would be said outright. Instead of saying that the home Darby built was majestic, Kristofferson writes that “the silhouette was seen for miles around / and the gables reached as high as the eagles in the sky.” Instead of telling that Darby was ultimately neglectful of his wife, he shares that Darby “never heard young Helen Darby crying.” And, ultimately, instead of saying that Darby walked in on his wife having sex with someone else, he dedicates the fourth verse to cinematically revealing that moment.

‘Darby’s Castle’ may be a little too on the nose—as Kristofferson was honing his craft, he consciously tried to simplify his lyrics—but it illustrates that one doesn’t truly hear a song by Kris Kristofferson until one has heard and mulled over its lyrics. It was no surprise that on his passport, he listed his occupation as a writer.

Indeed, Kristofferson’s songs had a writerly bent, especially the ones he penned early on. ‘Shadows of Her Mind’ was first recorded by Ed Bruce in 1967. Similar in scenario to the Beatles’ ‘Norwegian Wood (This Bird Has Flown)’ and almost as cryptic, Kristofferson substitutes poignancy for Lennon and McCartney’s cynicism. The song outlines a brief affair that is not transactional but instead a parable on the inability of a man to be a woman’s saviour. They meet in “the slowly falling rain,” they walk together hand in “trembling hand” and as they caress, the man wonders about “all the secrets she was keepin’ / hidden somewhere in the silence of the shadows of her mind.” Whatever the secrets were, they will never be revealed. Kristofferson never says exactly what happens to the woman but the final imagery of the man tracing her footsteps into the sea makes it painfully easy to guess.

‘Jody and the Kid’ is laced with similar humanity. It’s the story of a young boy and the young tomboy who trails behind him as the townsfolk call out “looky yonder, there goes Jody and the kid.” They grow older. The kid becomes a woman. Their affection grows for each other. If my reading of the lyrics are correct, they have a child but the woman is soon gone (again, Kristofferson never tells what happened to her). The void she has left is achingly clear as Jody walks with his daughter behind and “it’s gets a little lonesome when I hear / looky yonder, there goes Jody and the kid.”

The song was initially recorded by Roy Drusky in 1968 and become the first song by Kristofferson to become a hit. Drusky was in the mold of country crooners like Jim Reeves and especially Eddy Arnold. Kristofferson’s songs were a bridge between the old Nashville that Drusky exemplified and the new Nashville that Kristofferson heralded.

It was two years after he began to get an eager audience for his songs that Fred Foster signed him to Monument Records, the deal being clinched after Foster had seen him perform at the 1969 Newport Folk Festival, an appearance that was of Cash’s doing who had to coax a reluctant Kristofferson onto the stage. At first, he thought that Foster had signed him as a writer. He was mistaken.

Kristofferson protested to Foster that his singing voice was like a frog’s. There is truth to this. His voice was limited technically. The tone was never as rich as that of Waylon Jennings or Gibson or Ray Price or as distinctive as Cash or Nelson or Merle Haggard. His ability to sustain a phrase was sometimes lacking—the line petering out before its natural conclusion. Whatever shortcomings his voice had, they were obliterated by Kristofferson’s ability as a communicator and in choosing to sing his own songs, he showed that there is a singer within us all.

His debut album, titled simply Kristofferson, was released in June 1970. Foster surrounded Kristofferson with a crack team of the second generation of Nashville’s A-Team: guitarists Chip Young, Jerry Kennedy and Jerry Shook, bassist Norbert Putman, Buttrey and jack-of-all-trades Charlie McCoy with Bergen White handling the string arrangements. What resulted is a recording that has continually gotten better with age. Its foundation is the four songs that shot Kristofferson to the top echelon of Nashville scribes: the aforementioned ‘Me and Bobby McGee,’ ‘Help Me Make It Through the Night,’ ‘For the Good Times’ and ‘Sunday Morning Coming Down.’ Each would become a hit in the hands of someone else: respectively Janis Joplin, Sammi Smith, Price and Cash with innumerable covers versions of each to follow.

The power of Kristofferson, its durability if you like, comes from the songs that surround the quartet of classics. Several point to Kristofferson’s subversion of a Nashville and of a country music that was solidly conservative or, at the very least, agnostic politically. ‘The Law is For Protection of the People’ functions as a response to anyone who took Haggard’s ‘Okie from Muskogee’ as a literal hymn to square America. It scoffs at those who value security over the golden rule, ultimately implicating them in the crucifixion of Christ himself. It’s a message that still resonates—some may even argue that what Kristofferson rails against here is the true definition of “lawfare.” ‘Blame It on the Stones’ also sticks it to those who indulge in cheap moral panic, laced with several Rolling Stones-related musical jokes, but in a more dated menner.

‘The Best of All Possible Worlds’ join them as part of an informal trio of songs of cultural criticism. Here, Kristofferson amalgamates the surrealism of Dylan with the humour and wordplay of Miller and also throws in a reference to Voltaire’s Candide.

Then there are the song portraits. An understated ‘Darby’s Castle’ is here. ‘Duvalier’s Dream’ turns the scenario of ‘Seasons of Her Mind’ on its head. Instead of an affair resulting in unresolved desolation, a connections is made. ‘Casey’s Last Ride’ turns to the down and out, a drunk wandering the subways. The combination of Kristofferson’s roughened voice against a tough accompaniment evokes the grit of the New Hollywood emerging in 1970. It is contrasted by the almost-baroque lilt of the passages from the perspective of the woman powerless to turn Casey away from the ignominious end that surely awaiting him.

A need for some sort of deliverance is an underlying theme of many of the songs on Kristofferson. There is none to be found on ‘Just the Other Side of Nowhere’ where the people are colder than the weather. ‘Help Me Make It Through the Night,’ offered by Kristofferson in a version that lightly applies the sweetening of background vocals, narrows the runaway to one night—”let the devil take tomorrow / ’cause tonight I need a friend.” More than most, Kristofferson was able to see deeply into the truth of everyday life; that taking existence day by day was not simply a slogan but the only option available to get to the other side of midnight alive. There’s also that sometimes we need to say goodbye and, as such, ‘For the Good Times’ is about as clear-eyed about this unfortunate fact of life as can be and that’s why it’s as moving as it is.

Kristofferson’s recording of it is direct. Its truth speaks for itself. ‘Me and Bobby McGee,’ about appreciating the good in whatever situation one finds oneself, has a rustic feel—McCoy’s harmonica especially—and when I hear it, I think of movies like Cool Hand Luke or Bonnie and Clyde as opposed to La Strada which was the song’s primary inspiration.

‘Sunday Morning Coming Down,’ which closes Kristofferson, is as desolate as it is direct. Of a second beer in the morning for dessert and rummaging around for the “cleanest, dirty shirt” and of “[stumbling] down the stairs to meet the day.” The song is a punch in the gut, particularly in the context of hearing it as part of his debut album. The third and final verse has two pieces of religious imagery—children singing during Sunday school and the peal of a bell—signs of a possible redemption and, in a way, foreshadowing what happened to Kristofferson at a church service presided by Jimmie Rodgers Snow, son of Hank Snow, that would be immortalized in ‘Why Me.’

On ‘To Beat the Devil,’ Kristofferson writes about an encounter with the devil at a tavern who taunts him about the futility of trying to reach people through song, those whose “voices has been scattered by the swirlin’ winds of time / ’cause the truth remains what no one wants to know.” He rebuffs the devil and underlining Kristofferson as a stand-up-and-be-counted rebel, “I ain’t sayin’ I beat the devil / but I drank his beer for nothing / then I stole his song.” He then twists the devil’s words to affirm his purpose as an artist. He sings, “I was born a lonely singer and I’m bound to die the same / but I’ve gotta feed the hunger in my soul / and if I never have a nickel, I won’t ever die ashamed / ’cause I don’t believe that no one wants to know.”

Kris Kristofferson wouldn’t be a hungry singer for very long after Kristofferson was released. When he decided to spurn a more conventional life, that he may scuffle forever was not outside the realm of possibility but certainly the years Kristofferson spent in academia and other pursuits provided the backbone to give his songs a hard-earned and well-honed authority. There’s a guide to living in his music that provides an answer to any particular moment that may beg the question, “what would Kris Kristofferson do?”

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