Kris Kristofferson remained humble regarding his abilities.

He didn't like 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 sing like a bullfrog.'

Indeed," Foster responded, "a bullfrog capable of communication.

Kristofferson's straightforward vocals might not have shown much range, but 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 approach of not coercing songs into being — as he stated, "I would have to wait for inspiration to strike before I could write,” — but 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 alongside 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 long-lasting hits, Me and Bobby McGee It began as a songwriting challenge.

The founder of Monument Records, Foster, harbored a secret admiration for his secretary, Barbara "Bobbie" McKee, and sought out a song he believed would captivate her attention.

Kristofferson agreed to take on the task, yet discovering motivation proved elusive for him.

He stated in 1973 that he stayed away from Foster for about three or four months due to the constant stream of thoughts occupying his mind.

I was driving back to New Orleans one evening when the windshield wipers were moving, 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 once had been irretrievably lost.

Kristofferson transformed that narrative into the story of two wanderers who encounter love during their travels but are ultimately parted by death.

It includes one of his most remarkable lyrics: Freedom is merely a term for having nothing else to lose / What has no value isn't worth anything — yet it's free.

Initially performed by Roger Miller, the song achieved top billing as a number-one hit for Janis Joplin, who recorded it shortly before she passed away 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 through 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-fueled life.

The aroma of fried chicken makes him think of "something that I've lost."

He pauses outside a Sunday school merely to listen to the children's singing.

The intense feelings of isolation and self-hatred are clearly conveyed—Kristofferson mentioned that he penned these verses during his time as a struggling musician residing in an apartment building following his parents' rejection and when his spouse and offspring relocated to California without him.

He remarked that Sunday was the most difficult day of the week when one lacked a family.

Legend has it that Kristofferson delivered the song directly to Johnny Cash by piloting a helicopter into his yard and insisting on staying until he agreed to hear his demo tape.

Cash was so impressed that he played 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 that very year.

3) Assist Me in Surviving the Night

Kristofferson, alongside musicians like Willie Nelson and Waylon Jennings, was a key figure in the "outlaw country" movement, which challenged Nashville’s commercial dominance and creative constraints.

Talking about his position in the nation's sky, back in 1970, He informed The New York Times I am not anyone’s closest buddy.

Everyone insisted that I wouldn’t succeed in Nashville and advised me to move to California or New York instead.

He had offended the established order 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 performed (and reaching number one) by the female country artist Sammi Smith.

Kristofferson mentioned that the lyrics were inspired by an interview with Frank Sinatra.

When queried about his beliefs, Old Blue Eyes replied: "Alcohol, women, or a holy book... whichever gets me through the evening."

Smith's sensuous delivery was a subversive step forward for country music but Kristofferson's own version - croaky-voiced and dripping with hunger - is just as much of a thrill.

4) Jody and the Child

"The initial great song I composed," 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 imbued with nostalgia and longing, as the artist recounts a girl who once roamed about with him, "wearing her tiny blue jeans folded up above her knees."

As time passes, they develop feelings for each other, growing older together while continuing to walk hand in hand wherever 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 as well as heart-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 extra emotional depth.

5) Why Me?

If the character from Sunday Mornin' Comin' Down were at their lowest ebb, this depicts them as being utterly devastated.

" God, what have I possibly achieved / To be worthy of just one / Of the joys I've experienced? "

After participating in a service at Jimmie Snow's church in Nashville, Kristofferson felt inspired to compose the song.

Everyone was on their knees when Jimmy remarked, 'For anyone who’s misplaced, please lift your hand.' he said .

I rarely attend church, and raising my hand was completely out of the question.

I was thinking, 'I cannot fathom who might be behind this,' when unexpectedly my hand started rising.

Following his conversation with the preacher, Kristofferson mentioned, “I ended up crying in public” and experienced a sense of “forgiveness that I wasn’t aware I required.”

The track serves as a response to that instant—a poignant, somber acknowledgment of his previous actions, and an heartfelt plea for absolution.

Recorded alongside his future spouse, Rita Coolidge, the 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. It humorously dismisses common country music themes, showcasing the nascent growth of his narrative skills.

7) They Killed Him - A tribute to Kristofferson’s icons—Jesus, Gandhi, and Martin Luther King Jr.—later revisited by Dylan. "When Dylan covers one of your songs, it feels as though you’re a playwright and he’s Shakespeare performing in your production," Kristofferson remarked.

8) Loving Her Was Simpler (Than Any Other Thing I'll Ever Experience Again) - This song stands out as one of his most romantic tracks and marked Kristofferson's debut on 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 gestures of goodwill can come full circle. Cash reportedly referred to it as "possibly my favorite song written by any author."

10) Please Don't Reveal How the Tale Concludes - In what could be their final evening, two people hold onto each other tightly, cherishing every memory they've shared, praying for an end to this impending separation. Composed during the early '70s, Kristofferson first offered this song to Billy Bare before revisiting it alongside Rita Coolidge when their own union began falling apart. The resulting duet is profoundly moving.

• Kris Kristofferson, the singer and actor known for "Special," has passed away.
• View the best moments from Kris Kristofferson's performance at Glastonbury in 1997.