I wasn’t the kind of kid who cut school. I was always too much at odds with the world to cause that kind of trouble. I knew better than to squander what grace I was given. But he was too … what? Sexy? Hot? I didn’t really have the words for that commodity of lust, but I knew. And so, somehow, Tisha Floyd—or was it Lynn Steingass?—and I dodged school that day in 1976, took the Cleveland Rapid Transit, paid our money, and bought some popcorn. Nervously laughing, waiting for the roar of music that was the opening sequence of A Star Is Born, my heart was racing. And then: Kris Kristofferson in all his pepper-with-a-little-salt bearded and wavy-haired glory, sweaty and shirtless, brazen and reckless. 

I had long known about Kris Kristofferson. I watched him on The Johnny Cash Show in my Dr. Denton jammies as my father tried to decide whether he was a commie, a hero, or a bum. It was the early ’70s, and my father, a problem drinker who loved Tennyson, recognized the poetry and the stillborn shame in songs like “Sunday Morning Coming Down,” “Help Me Make It Through the Night,” “For the Good Times.” But Kristofferson had long hair, wore buckskin, had been a janitor—and, well, “those damned hippies.”

Before Waylon Jennings and Willie Nelson joined Cash and Kristofferson to become the Highwaymen, before the “outlaws” were a movement, I knew Kristofferson was trouble but honorable in his insurrection. Kristofferson’s biography was already legend by the time I saw A Star is Born: Rhodes Scholar, Phi Beta Kappa. He resigned his Army commission and gave up his Norman Rockwell American dream to go to Nashville to be a janitor at Columbia Studios where Dylan was making Nashville Skyline, while also flying helicopters to oil rigs in the Gulf of Mexico to make ends meet.  Eventually, the story goes, he landed one in Johnny Cash’s yard to hand him the demo of “Sunday Morning Coming Down.”

I was a kid, but even I knew that. And by 14, I found myself sucked into a tunnel of songs: “Angel from Montgomery,” “Green, Green Grass of Home,” “Fountain of Sorrow,” “Willin’.” They said what I couldn’t, what I didn’t know how to say, what I didn’t even know I was feeling. How much can be revealed in a simple melody carrying a few hundred words. 

Stories of drinking on credit at Tootsie’s Orchid Lounge, on Nashville’s seedy Lower Broadway and across the alley from the Ryman Auditorium, and wild times with Johnny Cash and Willie Nelson were writ as large as his image on the movie screen. For all the high jinks, he was mythic more than anything. 

After all of it, Kristofferson never lost his manners or his kindness. On the phone with a fledgling 19-year-old rock critic who had over-researched her assignment in the Miami Herald’s morgue and didn’t quite understand what she had read, he fielded a nonsensical question with grace. After the young lady again asked about “studying with William Blake,” the low rumble of gentle laughter came down the line like thunder on a summer afternoon. Then the legend gently explained, “Oh, honey … he’s dead.”

Did my silent scream register? Ever the gentleman, he finished the interview, considering my questions thoughtfully and offering answers that were perfect and quotable. When it was over, he insisted I have the promoter bring me backstage and he left passes to let me know he was serious. That night before he went onstage, he laughed a little bit about my interview, but more to lighten the horror than to make me feel small. He said he was surprised that a kid like me even knew to ask about William Blake, and his smile was like sunshine after a bad storm. He was smaller in person than he had seemed up on the screen of the Van Aken Center movie theater, but he was sinewy, solid, virile without being macho. He killed me.

The years came and went, and Kristofferson’s fortunes rose and fell. He drew lines and held them, and made decisions that some people thought were sketchy or career-destructive—that notorious spread in Playboy with Sarah Miles, Heaven’s Gate, songs about Sandinistas—but he never backed down. Watching him I learned to tell the truth, at all costs. 

It was thrilling to see him onstage in his plain black t-shirt, a Stratocaster slung low, with a craggy bunch of musicians, including the now-deceased Stephen Bruton, singing unadorned culture clashers like “Blame It on the Stones,” “Don’t Let the Bastards Get You Down,” “If You Don’t Like Hank Williams (Kiss My Ass),” “Shipwrecked in the Eighties,” and the tawdry “You Show Me Yours (And I’ll Show You Mine).” Kristofferson knew that “Jesus Was A Capricorn” and compared the great savior to the hippies the good Christians were decrying. He skewered his own Lothario tendencies with “The Silver Tongued Devil and I.” 

Few things are as sexy as integrity. In a world of pretty boys, it was Kristofferson’s convictions that took the girls’ breath away. A heartthrob named Connie Smith took the hard-living songwriter to church, where he approached the altar, dropped to his knees, and shortly thereafter wrote “Why Me” as he pondered all his blessings. And there was Janis Joplin, dead and gone, yet topping the charts posthumously with “Me and Bobby McGee,” singing “Freedom’s just another word for nothing left to lose …” If ever there was a siren’s song for a generation, that was it.

Long before Feeling Mortal, his new album-length meditation on the inevitable tapering of life, Kristofferson celebrated the battered dignity of the vulnerability, the bust-ups, and the failures that come with living life on one’s own terms. 

Just look at the canon, and its declarations. 

In “For the Good Times,” the singer refuses to buckle under, and appeals for one last moment of closeness from the woman he’s loved and lost: “Lay your head upon my pillow/Hold your warm and tender body close to mine/Hear the whisper of the raindrops blowing soft against the window/Make believe you love me … one more time/For the good times …”

“Help Me Make It Through the Night” shows us the same sort of broken man seeking comfort from a woman he knows he can’t keep. With the same elegance, he requests the woman take the ribbon from her hair, exulting in the sensual pleasure of watching it fall “soft upon my skin.” But this is more than savoring beauty, it is saving one’s own life. As the arrangement ramps up from bare to sweltering, the singer cries, “I don’t care who’s right or wrong, I don’t try to understand/Let the devil take tomorrow, Lord, tonight I need a friend.” After that extreme sentiment, the intimate scale that has always defined Kristofferson’s lyricism kicks in, “Yesterday is dead and gone, and tomorrow’s out of sight/And it’s sad to be alone, help me make it through the night.”

Somehow he always understands what exists beneath the surface of the moment, knows how to say it so we feel it, too. That’s what makes Feeling Mortal so poignant. Without liking it, he has come to terms with the dwindling of his time and the loss of some of his life force. It is not a weepy album, but a feisty look at the inevitable, and when you listen, you can only consider what is, and through these songs hold it a little closer. And so it has always been with Kristofferson: the hard road traveled with reverence, laughter at the absurdity of it all, and the love that underscores everything.

Sitting in my car listening to the raw-edged instruments, that voice like a creaky floor covered with gravel, I close my eyes and sink inside the songs. With the opening lines, he stares down the inevitable, and maintains the dignity that’s always been his benchmark. “Wide awake and feeling mortal, at this moment in the dream/That old man there in the mirror, and my shaky self-esteem/Here today and gone tomorrow, that’s the way it’s gotta be …” 

Once again, I’m gob-smacked. Gutting what is perhaps the gravest universal fear like a fish, he recognizes reality and meets it on his own terms. With a watchful eye, he considers the future, the life he’s lived, the morality he’s learned. His ultimate realization is found in “Bread for the Body,” a lean pirate shanty. With that familiar gravel-croak, Kristofferson professes, “I’m living my life by the lesson I’ve learned/And not looking back at the bridges I’ve burned/Cause the time that we travel from cradle to grave/Was meant to be spent and not meant to be saved.”

Like this story? Subscribe to the Oxford American.