Kris Kristofferson was the songwriter who helped country music grow up

As I delve into the captivating tale of Kris Kristofferson, a man whose life has been as tumultuous as a stormy sea, I find myself utterly enchanted by his journey. A songwriter par excellence, he redefined the boundaries of country music and left an indelible mark on the genre.


I can’t help but think that Kris Kristofferson might have been his own worst enemy with his extraordinary good looks, intelligence, and passion. These qualities are undeniably admirable, yet at times, they may have hindered rather than helped his songwriting journey. His struggles with alcohol and women were more self-inflicted setbacks, though.

While I was on a trip, far from my computer, the news of Johnny Cash’s passing at 88 years old became public. Upon returning to write about him just thirty-six hours later, I found that heartfelt tributes had already flooded in from various parts of the cultural sphere. Country music artists were among those who shared their thoughts most poignantly.

It could have been confusing for the younger Kristofferson, who moved to Nashville at age 29 in 1966 with just his rugged charm and an unconventional approach to lyrics. For several years, he struggled as a songwriter and had to take on jobs like cleaning one of Nashville’s numerous recording studios.

Kris Kristofferson was truly one of a kind

If you were born around the 1970s like me, with a lean towards rock & roll over country music, Kris Kristofferson might not have seemed particularly impressive as an artist back then. However, he was quite popular in several successful films during that decade due to his good looks. It’s important to note that this doesn’t mean he was a terrible actor; rather, he simply didn’t excel at it. He possessed an innate charisma that made him suitable for roles that complemented his personality. He was known for his sharp wit and sex appeal.

However, despite his eagerness to take on the role of a “movie star,” Kristofferson found it challenging when required to deliver subtle performances or steps outside his character. His intelligence was too keen to let him believe he was a top-tier actor. At times, it appeared as though he felt somewhat awkward being involved in Hollywood’s blockbusters.

It wasn’t until later we suburban teens realized that this man was extraordinary. He was a Rhodes scholar and ex-Army Ranger, who had narrowly escaped death during military training due to a malfunctioning parachute. Instead of letting it deter him, he saw it as a warning sign. Kris Kristofferson declined an opportunity to teach English at West Point, a role that seemed tailor-made for him, to follow his true love: composing country songs.

He had neither the look nor the temperament for the job. And he sure didn’t have the connections. This is how he came to be 29 years old, with a wife and family, working as a janitor in Nashville.

The town, its past, and its residents stirred him deeply. On one occasion, he found Bob Dylan laboring tirelessly on song lyrics at 4 in the morning, all by himself in the recording studio. Being able to pilot a helicopter, he transported some lyrics to Johnny Cash’s property from above. He was determined to make an impact and resorted to various strategies. Regrettably, for quite some time, none of his attempts bore fruit. (Paraphrased from your original text)

Eventually, people started to tune into the early tunes. Sharp-eared listeners soon realized that this rough, unpolished young man, who was merely average on the guitar and had a voice that only sounded pleasant when viewed through squinted eyes, was composing the most outstanding songs amidst a sea of songwriters in the city. And it wasn’t even a close call.

Kris Kristofferson was among the pioneers who initiated a divide within the country music scene that became more pronounced in the early ’70s and continues today. Initially, there was a traditional, conservative form of country music that focused on love songs and ballads about heartache, typically performed by polished session musicians, enveloped in strings, backed by choirs, and sung by neatly groomed artists with pristine voices.

In contrast, a more unconventional and rebellious style of country music emerged, shaped by young, progressive artists who had been nurtured on rock music. These artists didn’t fit the stereotype of a traditional country star in appearance or sound. Kristofferson served as their symbol.

He wrote songs about having sex, about not having sex, and about getting drunk when you weren’t having sex. He wrote them with the attention to detail and sense of narrative that are the hallmarks of great authors. Kris Kristofferson was a scholar, and he knew the classics, whether it was William Blake or Hank Williams.

In the early days, Nashville had reservations about songs like “Help Me Get Over,” “Mature Times,” “Sober Sunday Mornings,” and “Laws Are for the People.” They found these tunes to be overly candid, mature, and politically charged. Country radio stations refused to air them, and record labels hesitated to let their artists record them. However, the songs were still produced due to their exceptional quality. Artists with influence in the industry took a stand and released these records, regardless of label approval. The country music audience eagerly embraced these grown-up tunes, indicating that they deserved serious consideration.

Kris achieved his greatest triumph as a lyricist when tasked to compose a tune about the receptionist at Monumental Records, the company where he initially secured a contract. Her name was Bobbie McKee; Kris slightly altered the last name to create “Me and Bobby Maggie.” The song garnered widespread interest, with many artists eager to perform “Me and Bobby Maggie.

Janis Joplin, his occasional girlfriend, produced the iconic rendition of the song shortly before her untimely demise. Kris Kristofferson didn’t get to listen to that recording until after Joplin had passed away. The lyric “Freedom’s just another word for nothing left to lose” would eventually become one of the most poignant lyrics of a particularly tumultuous period in history.

Kristofferson penned all his own songs, yet wasn’t widely recognized as an exceptional vocalist. He acknowledged this fact, as others found success with his tunes. One of these singers was Rita Coolidge, whom he married in 1973 after she recorded a few of his songs. Their duet on “From the Bottle to the Bottom,” one of Kristofferson’s compositions, earned them a Grammy in 1974. This was approximately when the entertainment industry started showing interest in him.

Kristofferson, similarly to Willie Nelson and Waylon Jennings, departed Nashville at approximately the same period. Unlike Willie and Waylon who predominantly settled in Austin, however, Kris chose Los Angeles as his new home. The excessive drinking and womanizing that had been a significant aspect of his life escalated alongside his growing fame as a movie star. It became all too effortless for him. Consequently, his songwriting lost its luster, and his marriage disintegrated.

Subsequently, about ten years passed, and he teamed up with Willie, Waylon, and Johnny Cash to create one of the legendary musical ensembles – the Highwaymen. They were four veterans from the country music battlefield, four companions, four adversaries. Four men who had endured a lot, in terms of their careers and personal lives, now decided to collaborate for some enjoyment. The traditionalist Jennings and the outspoken progressive Kristofferson frequently found themselves on the brink of a fight, but the underlying affection and admiration – coupled with a timely joke from Willie Nelson – kept their friendship intact.

In one of his statements, Waylon Jennings expressed about Kris Kristofferson, “He has a shabby appearance, yet, my goodness, what a gifted songwriter.” I discovered many insights about Kristofferson, together with his fellow Highwaymen members, from Brian Fairbanks’ remarkable book “Willie, Waylon, and the Boys,” published in 2024. Cash is quoted by Fairbanks as saying upon hearing “Help Me Make it Through the Night” for the first time, “That man is a poet. It’s unfortunate he can’t sing well.

And he quotes Willie, now the last remaining Highwayman, as saying about Kris, “He shows more soul blowing his nose than the ordinary person does at his honeymoon dance.”

Initially, many believed that some of Kristofferson’s soul was lost after his early songs – songs that significantly altered the essence of what country music could encompass. However, it’s also widely thought that his collaborations with Coolidge and the Highwaymen kept him relevant in the music industry. To a certain extent, there is validity to this perspective.

Kris Kristofferson didn’t simply lose his knack for composing magnificent songs; furthermore, his ardor for significant matters never waned. What many young audiences might recognize most is his defense of Sinead O’Connor, penned in 2009, a time when it was thought he had ceased to be influential in the music world. Remarkably, many songwriters would envy crafting a chorus as poignant and sublime as this one.

Perhaps she’s not all there, perhaps she is sane

Now that he’s departed, it’s clearer than ever that the songs Kris Kristofferson penned, whether consciously or subconsciously, were not only about Sinead O’Connor. Instead, they mirrored his own experiences.

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2024-10-01 16:00