Kris Kristofferson: Top 5 (or Maybe More) Essential Tracks
Kris Kristofferson remained humble regarding his abilities.
He was not fond of being referred to as a poet and enjoyed it more when others would perform his songs instead.
He once confessed to record producer Fred Foster, 'I croak like a bullfrog.'
Indeed," Foster responded, "a bullfrog capable of communication.
Kristofferson's straightforward vocals might not have shown much range, yet they conveyed something far more crucial: conviction.
Whenever he performed about heartbreak, romance, melancholy, wild evenings, and remorseful dawns, you found yourself believing each syllable.
This was partially due to his refusal to coerce a song into being — as he stated, "I always waited for inspiration to strike before writing it" — and also because he possessed an ability to delve into the fundamental essence of emotions.
Although his songwriting wasn’t particularly intricate, the way he used simple chord progressions along with clever turns of phrase sparked a revolution in country music.
"You can observe Nashville before Kris and after Kris, as he transformed everything," Bob Dylan once stated.
These are some of his most notable tracks.
1) Me and Bobby McGee
One of Kristofferson's most lasting hits, Me and Bobby McGee It began as a songwriting challenge.
The founder of Monument Records, Foster, developed a liking for his secretary, Barbara "Bobbie" McKee, and sought out a song he believed would make an impression on her.
Kristofferson accepted the assignment - but finding inspiration took time.
He mentioned in 1973 that he steered clear of Foster for about three or four months due to the constant barrage of thoughts swirling in his mind.
I was driving back to New Orleans one evening when the windshield wipers were on, and everything began coming together.
He drew inspiration for the song from the final scene of Fellini’s movie "La Strada," where a disheartened, intoxicated man gazes despondently at the ocean, lamenting how his existence has unraveled and the affection he has squandered.
Kristofferson transformed that narrative into the story of two wanderers who discover love while traveling, only for their romance to be ultimately torn apart by death.
It includes one of his most remarkable lyrics: Freedom is merely another term for having nothing left to lose / What has no value isn't worth anything — except it doesn't cost a thing.
Initially performed by Roger Miller, the song achieved top billing as a number-one hit for Janis Joplin, who recorded it just weeks prior to her passing in 1970.
2) On Sunday Morning, It's Coming Down
When I woke up on Sunday morning, every movement made my head throb.
"And the beer I had for breakfast wasn't bad, so I had one more for dessert."
The bleakness conveyed by Kristofferson's somber performance indicates that this track delves deeper than just being about a mere hangover.
As it advances, the main character gradually discloses more information regarding the reasons behind his alcohol-filled life.
The aroma of fried chicken brings back memories of "something I had lost."
He pauses near a Sunday school simply to listen to the children's singing.
The intense feelings of isolation and self-hatred are portrayed powerfully — Kristofferson mentioned that he penned the lyrics during his days as a struggling musician residing in an apartment building after his parents rejected him, and when his spouse and child left for California without him.
He remarked that Sunday was the most difficult day of the week for those without family.
As the story goes, Kristofferson piloted a helicopter into Johnny Cash’s yard, insisting he wouldn’t depart until Cash had heard his demo tape.
Cash was so impressed that he featured the song on his American television show.
The Country Music Association awarded his recorded song of the year in 1970.
Kristofferson's own version emerged on his first studio album the same year.
3) Assist Me in Surviving the Night
Kristofferson, alongside fellow musicians like Willie Nelson and Waylon Jennings, was an integral part of the "outlaw country" movement that challenged Nashville’s commercial dominance and creative constraints.
In 1970, when discussing his position within the nation's political landscape, He informed The New York Times I am not anyone’s closest confidant.
Everyone insisted that I wouldn't succeed in Nashville and advised me to move to California or New York instead.
He had angered the powers that be with tracks like "Blame It on the Stones" and "The Law Is for the Protection of the People," both of which criticized American conservatism.
His most famous song Additionally, it caused controversy due to its frank portrayal of sexual longing, particularly when it was recorded (and reached number one) by the female country artist Sammi Smith.
Kristofferson mentioned that the inspiration for the lyrics came from an interview with Frank Sinatra.
When questioned about his beliefs, Old Blue Eyes replied: "Alcohol, women, or a holy book... whichever gets me through the night."
Smith’s sensual performance marked a rebellious advance for country music, yet Kristofferson’s rendition—marked by his hoarse voice and palpable longing—is equally exhilarating.
4) Jody and the Child
"The initial great song I penned," Kristofferson stated regarding Jody and the Kid, which he created during his time as a janitor at Columbia Records in the 1960s
Similar to "Me and Bobby McGee," this piece is filled with nostalgia and longing, as the artist recounts a girl he once walked everywhere with, mentioning "her little blue jeans folded up above her knees."
Over time, they fall in love, and grow old, still walking hand in hand everywhere they go.
When the music stops, the storyteller walks along familiar routes with his daughter—yet upon meeting neighbors who approach him, he mourns that his spouse can’t be part of this moment.
Kristofferson's solemn, emotionally charged voice is mesmerizing and wrenching.
It’s equally worthwhile to listen to his 1999 re-recording of the song on the album "The Austin Sessions," as his more mature, rugged vocals add an extra layer of emotion to it.
5) Why Me?
If the character from Sunday Mornin' Comin' Down was experiencing a dip, this illustrates them hitting an all-time low.
" Lord, what have I ever done / To deserve even one / Of the pleasures I've known? "
After participating in a service at Jimmie Snow's church in Nashville, Kristofferson felt inspired to pen the song.
Everyone was on their knees when Jimmy remarked, 'Anyone who can’t find their way, lift your hand.' he said .
I rarely attend church, and lifting my hand was completely off-limits.
When suddenly I noticed my hand raising, I thought, 'I can’t fathom who might be behind this.'
Following his conversation with the preacher, Kristofferson mentioned, “I ended up crying in public” and experienced a sense of forgiveness he hadn’t realized was necessary.
The song serves as a response to that instant—a poignant, sorrowful acknowledgment of his previous actions, coupled with an earnest plea for absolution.
Recorded alongside his future spouse, Rita Coolidge, the song was produced. gospel-infused ballad resonated deeply with listeners in 1973, earning the lead performer their sole top spot on the country music charts.
Additional Listening: Five More Essential Tracks
6) I Dislike Your Unattractive Appearance - The initial song penned by Kristofferson when he was 11 years old. This sarcastic dismissal of common country music themes showcases the early signs of his skill in narrative writing.
7) They Killed Him - A tribute to Kristofferson’s icons—Jesus, Gandhi, and Martin Luther King Jr.—later revisited by Dylan. "Getting Dylan to perform one of your songs is akin to writing a play and having Shakespeare star in it," according to Kristofferson.
8) Loving Her Was Simpler (Than Any Other Thing I Will Ever Experience Again) - This song stands out as one of his most romantic tracks and was Kristofferson's initial entry onto the charts in 1971. It was revisited years later when he performed it again alongside The Highwaymen, an influential supergroup comprising outlaw country musicians including Cash, Jennings, and Nelson.
9) There Goes That Rainbow Once More Inspired by a passage from John Steinbeck’s novel *The Grapes of Wrath*, this poignant ballad revolves around how minor acts of generosity can come full circle. Cash himself remarked that it might be his favorite song penned by any author.
10) Please Don't Reveal How the Tale Concludes - A pair of lovers share one final evening together, holding onto their cherished recollections and each other, praying that their unavoidable separation will not occur. Composed in the early '70s, Kristofferson first offered this song to Billy Bare before revisiting it alongside Rita Coolidge when their own union was disintegrating. The resulting collaboration between them is profoundly moving.
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