Kris Kristofferson has left an indelible mark on the world of country music with his profound lyrics and soulful melodies. His songs are testaments to his exceptional ability to convey poignant stories through music.
In this article, we reflect on some of the timeless tracks by the legendary songwriter, who passed away at the age of 88. We explore the impact and stories behind five (or maybe 10) of his most memorable songs.
Me and Bobby McGee
One of Kristofferson’s most enduring songs, Me and Bobby McGee, started out as a songwriting challenge. Monument Records founder Fred Foster had a crush on his secretary, Barbara ‘Bobbie’ McKee, and wanted a song that would impress her. Kristofferson accepted the assignment, but inspiration took time to come.
‘I avoided him [Foster] for three or four months because there were only thoughts running through my head,’ Kristofferson said in 1973. ‘I was driving back to New Orleans one night, the windshield wipers were going, and it started falling together.’ He based the song on the last scene of the Fellini film La Strada, turning it into a story of two drifters separated by death.
Originally recorded by Roger Miller, Me and Bobby McGee became a number-one hit for Janis Joplin, who recorded it weeks before her death in 1970. The song is revered for its poignant lyric, ‘Freedom’s just another word for nothin’ left to lose / Nothin’ ain’t worth nothin’ – but it’s free.’
Sunday Mornin’ Comin’ Down
The desolation of Kristofferson’s downbeat delivery in Sunday Mornin’ Comin’ Down tells you this song is about much more than a bad hangover. As the song progresses, the protagonist reveals more about his booze-soaked existence, with the smell of fried chicken reminding him of ‘something that I’d lost.’
The song paints a vivid picture of loneliness and self-loathing. Kristofferson wrote the lyrics as a struggling musician living in a tenement, after his parents disowned him and his wife and child moved away.
According to legend, Kristofferson got the song into Johnny Cash’s hands by landing a helicopter in his backyard. Cash was impressed enough to play the song on his TV programme, and it was named the Country Music Association’s song of the year in 1970.
Help Me Make It Through the Night
Kristofferson was part of the ‘outlaw country’ scene that resisted Nashville’s commercial and creative constraints, with Help Me Make It Through the Night becoming one of his most famous songs. The lyrics were inspired by Frank Sinatra, who said he believed in ‘Booze, broads, or a bible… whatever helps me make it through the night.’
Sammi Smith’s recording of the song took it to number one, and her sensuous delivery was a subversive step forward for country music. However, Kristofferson’s own version—croaky-voiced and dripping with hunger—is equally compelling.
Kristofferson had previously upset the establishment with songs like Blame It on the Stones and The Law Is for the Protection of the People, which critiqued American conservatism. In the context of these other works, Help Me Make It Through the Night stands out as a raw portrayal of human desire.
Jody and the Kid
Jody and the Kid is the first good song Kristofferson said he wrote, composed while working as a janitor at Columbia Records in the 1960s. It captures nostalgia and loss, describing a girl who used to walk everywhere with him, eventually falling in love and growing old together.
As the song ends, the narrator traces their old paths with their daughter, now lamenting the absence of his wife. Kristofferson’s sombre, emotional vocal is both spellbinding and heartbreaking.
Listeners often find deeper meaning in Kristofferson’s older voice, as heard in his 1999 re-recording of the song on The Austin Sessions album, which adds additional pathos to an already emotional track.
Why Me?
Why Me? stands out as a soul-cry for forgiveness and a reflection of Kristofferson’s rock-bottom moment. Inspired after attending a service at Jimmie Snow’s church in Nashville, Kristofferson felt a ‘forgiveness that I didn’t even know I needed.’
The song’s mournful realisation of past behaviour resonated with audiences, with Kristofferson recording it alongside his soon-to-be wife, Rita Coolidge. Why Me? became his only number one hit on the country charts in 1973.
The gospel-infused ballad captures a moment of profound personal reckoning and has since become a staple in Kristofferson’s repertoire, offering insight into the depth of his songwriting and personal journey.
Further Listening: Five More Essential Songs
For those who wish to delve further into Kristofferson’s catalogue, five additional songs are essential. I Hate Your Ugly Face, written at age 11, showcases early storytelling talent.
They Killed Him is a lament for his heroes, later covered by Bob Dylan. Loving Her Was Easier (Than Anything I’ll Ever Do Again) is one of his most romantic songs and first chart hits, later re-recorded with The Highwaymen.
Here Comes that Rainbow Again, inspired by John Steinbeck’s The Grapes of Wrath, reflects small acts of kindness being repaid. Please Don’t Tell Me How the Story Ends explores the hope of clinging to memories amidst the pain of an inevitable breakup.
Kris Kristofferson’s songs are a testament to his remarkable talent and ability to connect with listeners on a deep emotional level. His legacy lives on through his timeless music.
From poignant ballads to groundbreaking hits, Kristofferson’s work has left an enduring impact on the country music landscape. His songs will continue to be cherished and celebrated by fans for generations to come.
