In a Kris Kristofferson Song, a Hard Life Never Made You a Loser

David Hinckley
5 min readOct 1, 2024

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Let’s just say Kris Kristofferson didn’t have the typical country music resume.

Kristofferson, who died Saturday at the age of 88, was a Rhodes Scholar and a political progressive. When he put a touring band together in 1970, he recruited Zal Yanovsky, late of the Lovin’ Spoonful, as his lead guitarist. Some years down the road, what coaxed him out of performance retirement was the chance to sing Elvis’s “All Shook Up” and the Beatles’ “Paperback Writer.”

But when it came to writing songs, which is what Kris Kristofferson did best, he nailed the essence of country music: Tell a good story and set it to a tune that sounds good even when you sing along out of tune.

Like Hank Williams, Harlan Howard and, to be fair, the best songwriters in popular music, Kristofferson needed only a couple of verses to paint a picture that could tell you everything about a single moment (“Help Me Make It Through the Night”) or a whole life (“Sunday Morning Coming Down”).

He wrote a lot of songs, not all of them great. No one writes all great. But his best songs, from big hits like “Loving Her Was Easier Than Anything I’ll Ever Do Again” and “Please Don’t Tell Me How the Story Ends” to less-remembered gems like “Stranger” and “Come Sundown,” nailed the world that intrigued him the most, the world of restless drifters trying to figure it out.

Hank Williams distilled that world into “I’m So Lonesome I Could Cry,” and country music long ago made an art form out of songs about crying in your beer.

Kristofferson gave the premise a twist. His drifters haven’t given up or given in. They understand what’s happened and while they may be helpless to stop it, they don’t surrender. They focus on getting from tonight to tomorrow morning, or noon to midnight. One foot in front of the other, however low their expectation for what’s ahead on the path.

In “Stranger,” a №4 hit for Johnny Duncan and Janie Fricke in 1976, Janie takes a one-nighter because the alternative is a no-nighter, and she will not be let down because neither she nor he has illusions about more.

“Maybe you got all you got together,” she tells Johnny. “Maybe you keep rollin’ like a stone / Maybe some old lonesome song’ll take you by surprise / And leave you just a little more alone.”

If this leaves the story floating in the mist, that’s one of the things Kristofferson was really good at. His songs, like life, rarely wrapped anything up.

That was even true in “Come Sundown,” where the singer knows exactly what will happen next and how powerless he is to stop it:

“And I curse the sun for rising

’Cause the worst, Lord, is yet to come

This morning she’s just leaving

Come sundown, she’ll be gone.”

He could throw curveballs. Two years after his smoking-and-drinking picker made the most cursory passing note of church hymns in “Sunday Morning Coming Down,” the singer in “Why Me” was on his knees at the front of the congregation.

“Why Me ” was Kristofferson’s only solo №1 hit. In fact, it was his only solo song to crack the top 60, which correctly suggests his greater impact came as a writer. Not a problem. By the time Roger Miller, Jerry Lee Lewis, Johnny Cash and Ray Price were recording his songs, around the late ’60s, lines were forming to get Kristofferson material.

Happily, most songs ended up with the right singers. Lewis was far more appropriate than Price for the stomping “Once More With Feeling.” Price’s smooth style worked better than Lewis or Cash on “For the Good Times,” which conjured two people in a quiet room with a final glass of wine.

Then, too, more than 250 other artists have recorded “For the Good Times,” so it’s had a variety of treatments.

Roger Miller, no amateur himself with song lyrics, didn’t sound like Janis Joplin doing “Me and Bobby McGee.” They both, in their own way, nailed it.

Lyrically, “Me and Bobby McGee” may have helped explain why Kristofferson and Bob Dylan had a long-running mutual admiration society. Two famous lines in “Bobby McGee” — “I’d trade all my tomorrows for a single yesterday” and “Freedom’s just another word for nothing left to lose” — would make you roll your eyes if you heard them from a slightly tipsy college sophomore. For the song, they form perfect cornerstones.

Kristofferson also sprinkled his songs with wit, though songs like “Help Me Make It Through the Night” didn’t really lend themselves to laugh lines. He did wedge at least one into “Sunday Morning Coming Down”: “The beer I had for breakfast wasn’t bad, so I had one more for dessert.”

With Sinead O’Connor at MSG.

Kristofferson eventually became known for a variety of things beyond songwriting. He joined Cash, Willie Nelson and Waylon Jennings in the Highwaymen, a rough-edged living history quartet that recorded, toured and was a lot of fun to listen to. He carved out a pretty successful acting career, playing opposite Barbra Streisand in a remake of A Star Is Born, popping up in all three Blade movies and turning Shake Tiller into a skinny wide receiver in Semi-Tough. He also had a cameo in Sinead O’Connor’s famous non-performance for the 1992 Dylan “Bobfest” concert at Madison Square Garden. When she paused because she felt the audience was getting hostile, he came on-stage to whisper, “Don’t let the bastards get you down.”

That was, not coincidentally, the title of a song he had recorded two years earlier, after he had decided to write some overtly political material.

At one point during that period he was on a talk show and the conversation turned to Laura Ingraham’s book Shut Up and Sing, in which she laments artists interjecting politics into their music. “I am singing,” he said. “Shut up and listen.”

As with most artists, we get to pick the parts of Kris Kristofferson we like best. He didn’t sing “My Way,” praise the Lord, but he kind of lived it.

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David Hinckley

David Hinckley wrote for the New York Daily News for 35 years. Now he drives his wife crazy by randomly quoting Bob Dylan and “Casablanca.”