Kris Kristofferson’s songs felt as big and nuanced as life itself

Forged in patience and courage, his songbook captured life and death in staggering detail.

Singer-songwriter and actor Kris Kristofferson at the 1971 Schaefer Music Festival in New York City. (Don Paulsen/Michael Ochs Archives/Getty Images)

Column by Chris Richards

September 30, 2024 at 3:06 p.m. EDT

Imagine writing a song as good as “Sunday Mornin’ Comin’ Down.” It must have felt like building the Brooklyn Bridge with your bare hands. “There’s something in a Sunday that makes a body feel alone,” the ballad’s demolished narrator sings through his hangover as he embarks on a weekend stroll in the direction of the void.

Instantly, your body feels everything his body feels. The dull agony of simply waking up. The relief of dousing a headache with two beers — one for breakfast and “one more for dessert.” The cool tingle of that “cleanest dirty shirt” on your back. The sound of your shoes plodding down an empty sidewalk, their forsaken rhythm mingling with the laughter of children, and the clang of church bells, and the smell of home cooking as it twists out of a kitchen window in Looney Tunes contours. If you’re really listening to all this, you’ll feel desolation, then wonderment. How does a song about falling apart feel this sturdy, this colossal, this magnificent?

When people use words like “magic” and “genius” to explain the provenance of great art, what they’re usually talking about is “experience,” which is something Kris Kristofferson had loads of. The Texas-born singer-songwriter, who died Saturday at 88, seems to have lived nearly half a dozen lives before he even got to Nashville. In college, he was a Golden Gloves boxer who wrote short stories that were published in the Atlantic. In 1958, he went overseas on a Rhodes Scholarship to study literature at Oxford but left before earning his degree to become a helicopter pilot in the U.S. Army. He finally relocated to Nashville in the mid-’60s, patiently waiting for the perfect moment to make the impossible leap from janitor to professional songwriter.

He was good at everything, which was a strange way of being lost. Fortunately, he touched down in Tennessee when the minds of Johnny Cash and Willie Nelson were approaching full bloom, when the songwriters of Music Row were beginning to think more like poets, when the listening public had decided to broaden its notions of how much life and death a country song could convey. Also fortuitous: The mop that Kristofferson pushed for a living had been sloshing across the floors of the Columbia Studios. This reportedly allowed him to float a demo in the direction of Cash, who eventually recorded “Sunday Mornin’ Comin’ Down” in 1970. In Cash’s godly baritone, the song sounded indestructible. More like the pyramids at Giza than some bridge. But when Kristofferson recorded his existentially lonesome rendition for a self-titled debut that same year, God was nowhere to be found.

Loneliness and togetherness, living and dying. These are common paradoxes in country music. But very few songwriters explored their symbiotic balance with greater nuance than Kristofferson. Yes, “freedom’s just another word for nothin’ left to lose,” he sang, plain-voiced and righteous, on his signature hit, “Me and Bobby McGee” — but why does that line sometimes sound silver medal profound compared with “them windshield wipers slappin’ time,” their soggy friction so perfectly capturing our messy, mundane journey through existence? Forget about freedom for a second. Is death when it stops raining?

All these layers of philosophical detail made Kristofferson a songwriting giant in country music, just as his onstage charisma quickly caught the attention of various Hollywood directors (Sam Peckinpah, Martin Scorsese) who cast him in their films throughout the 1970s. So his big life somehow grew wider. In the ’80s, he began pushing his political beliefs to the fore, speaking out against U.S. involvement in Central America both in the press and in song. In 1985, he settled into legend status as a member of the Highwaymen, the storied outlaw supergroup with Cash, Nelson and Waylon Jennings, in which Kristofferson emerged as the most outspoken pacifist of the four. In a 1991 Highwaymen interview, when asked about the state of the nation on the brink of the Iraq War, Kristofferson said, “It reminds me a lot of the flag-waving and choreographed patriotism that we had back in Nazi Germany a half a century ago … [with a] lap dog media that’s cranking out propaganda for the administration that’d make a Nazi blush.” Nuance was a resource he saved for his songs.

Inside his music, though, his fearlessness felt delicate, even when he seemed to be facing down death. Kristofferson spent the final decades of his life touring through various health problems, and at a concert in 2017, upon finding his “cleanest dirty shirt” for the thousandth time while strumming the aching chords of “Sunday Mornin’,” he flashed an intimate grin and told the audience, “I’m wearin’ it.”

This was a laugh line, a tether for us to grab onto as we circled the darkness, and most certainly a lie. There’s no way this beautiful man had retrieved that beautiful shirt out of his hamper. But what’s really clean in this dirty world? Where does our living end and our dying begin? Are we ever truly alone, or are we always? If you can’t hear the answers in a Kris Kristofferson song, try the windshield wipers.