Subscribe to our newsletter

(Credit: Alamy)


How 1985 defines Kris Kristofferson forevermore


The term “renaissance man” is a little long in the tooth. The idea that an artist can flit between medium and style at the drop of a hat is now something that we expect of our musicians, filmmakers and writers. We want to see our favourite singers, actors or novelists lend their hand to projects and titles that are out of their expected reach. But while the idea is now perhaps a little out of fashion as an outlier of an industry, there is one man who can rightfully take the accolade with glee — Kris Kristofferson.

Born in Brownsville, Texas, Kristofferson isn’t just a wildly talented songwriter, nor simply a wonderfully gifted actor and sincere writer; he is also the founder of one of the greatest supergroups of all time. By 1985, with many of his artistic objectives completed, Kristofferson decided that he needed a few more friends alongside him to go on tour and invited Willie Nelson, Waylon Jennings and Johnny Cash to create perhaps the finest supergroup ever; The Highwaymen.

Kristofferson was always destined for greatness. It would appear that he was as gifted, intelligent, committed, and determined as anybody could’ve expected. He won prizes for his writing at an early age, featuring in The Atlantic Monthly with several of his essays. It didn’t take long for fame to find the naturally buoyant Kristofferson. In 1958, he was featured in the Sports Illustrated feature ‘Faces in the Crowd’, which picked out the singer for his huge achievements in collegiate sport. Studying literature, Kristofferson was beginning his long path to glory.

Having studied at Pomona College in California, Kristofferson was then provided with a decisive turning point in his life as he was offered the prestigious Rhodes Scholarship to Oxford University. It was here that he connected with Larry Parnes, who pushed Kristofferson into songwriting as a way of achieving his end goal of becoming a novelist. Labelled as “a Yank at Oxford” and recording under the alias Kris Carson, it was the first taste of the singer’s impressive career.

Before it would take full flight, Kristofferson enrolled in the US Army under pressure from his family. Commissioned as a second lieutenant, he attained the rank of captain and even became a helicopter pilot while in service. In 1965, Kristofferson was offered the opportunity to teach English literature at the famed US academy West Point but turned it down to pursue music.

Kristofferson moved to Nashville and began pursuing the life of a musician as he struggled to make ends meet and pay the medical bills for his son who was suffering from a defective oesophagus. Kristofferson soon got a job sweeping floors at Columbia Recording Studios and even met June Carter there, where he asked her to pass on a tape to Johnny Cash. Sadly, it found itself thrown on a heap of demos and was never given a second look.

Instead, Kristofferson went about continuing his work wherever he could get it, including a job as a helicopter pilot for Petroleum Helicopters International, which was based in Lafayette, Louisiana; it provided the budding musician with a chance to pen some song, about which Kristofferson said: “That was about the last three years before I started performing, before people started cutting my songs. I would work a week down here [in south Louisiana] for PHI, sitting on an oil platform and flying helicopters. Then I’d go back to Nashville at the end of the week and spend a week up there trying to pitch the songs, then come back down and write songs for another week. I can remember ‘Help Me Make It Through the Night’ I wrote sitting on top of an oil platform. I wrote ‘Bobby McGee’ down here, and a lot of them [in south Louisiana].”

Flying helicopters would also land Kristofferson his big break. The rumours surrounding this moment are rife, but there’s one thing we can guarantee: Kris Kristofferson landed a helicopter in Johnny Cash’s garden so that he could get the singer’s attention and ensure his next tape was given directly to him. Ideas that Kristofferson arrived with a beer in one hand and his demos in the other is unlikely as the man himself admitted: “It was still kind of an invasion of privacy that I wouldn’t recommend. To be honest, I don’t think he was there… John had a pretty creative memory.”

However it happened, after Cash heard ‘Sunday Mornin’ Comin’ Down’, he knew how talented Kristofferson was. He recorded the song, and that year Kristofferson won Songwriter of the Year at the Country Music Awards. From then on, Kristofferson became hot property. Dave Dudley released his song ‘Viet Nam Blues’ to widespread acclaim, later Jerry Lee Lewis. Ray Stevens and Roger Miller would all find success with Kristofferson originals, perhaps most famously from Janis Joplin, who produced her own wailing take of ‘Me and Bobby McGee‘. But, unlike his contemporaries, it was clear that Kristofferson wasn’t just happy to act as a musician.

Having released a few albums under his own name and found some success as a songwriter for the country’s finest, Kristofferson set himself a new challenge and began taking on acting roles. Within a few short years, Kristofferson had already amassed a heap of impressive roles including Sam Peckinpah’s Pat Garrett and Billy the Kid and Blume in Love from Paul Mazursky. He took roles in Martin Scorsese’s starring in Alice Doesn’t Live Here Anymore, Vigilante Force from 1976 as well as another hit from that year A Star Is Born.

For many, this is where the story would end. Countless musicians have tried their hand at Hollywood and usually fall out of love with the craft within a few years, normally as their star and novelty begins to fade. Kristofferson, however, stuck at it and continued starring in films such as Blade and Planet of the Apes up until 2006’s Disappearances.

But perhaps Kristofferson’s finest moment, aside from all the starring roles and wonderful songs, is how he joined Willie Nelson, Waylon Jennings, himself and Johnny Cash together in the autumns of their careers to form The Highwaymen. It was a serious line-up that demanded the attention of the music newspapers of the day. The band’s signature songs include ‘Highwayman,’ ‘Desperados Waiting for a Train’ and ‘Silver Stallion’, all of them the dusty western classics you’d hope them to be, are a perfect reminder of the potency of each member.

The band formed in 1985, and it proved to be a year full of impressive achievements for Kristofferson. The actor starred in Alan Rudolph’s Trouble in Mind and released an album filled with dark political anthems titled Repossessed, which once again proved that Kristofferson is the undoubted “renaissance man” of rock and roll. It may not have been the singer’s vintage year, nor necessarily a moment that signified the dwindling of a career. No, 1985 was a moment in Kristofferson’s life where he was entirely firing on all cylinders.

As the acclaimed songwriter, actor and novelist settles into his 85th year on this planet, it seems only fitting that we should celebrate the life and times of one of America’s finest artists by reflecting on the myriad of ways he has enriched our lives.