I Was Thinking About…The Interesting Life of Kris Kristofferson
By Andy Lee
Kris Kristofferson has lived one of the most fascinating and unorthodox lives in music history. Guided by fierce creativity and individualism, his incredible journey twisted and turned through many chapters on the path to becoming an acclaimed singer-songwriter and actor.
Born in Texas in 1936, Kristofferson came from a military family but was destined for creative endeavors. He excelled as a student-athlete, playing football and running track while also writing essays and poetry. His impressive academic achievement gained him selection as a Rhodes Scholar at Oxford University.
At Oxford, Kristofferson graduated with a BPhil (Bachelor of Philosophy) in English literature. He was a standout on the rugby pitch and football field. He also competed as a boxer, becoming a Golden Gloves champion. During this time, Kristofferson first began writing songs, inspired by Romantic poets like William Blake who resonated with his independent spirit.
After Oxford, Kristofferson joined the U.S. Army as expected of him. He completed Ranger training and became a helicopter pilot, eventually achieving the rank of Captain. Kristofferson volunteered to be a helicopter pilot in Vietnam, but the Army assigned him to teach English at West Point instead.
Restless in the rigid military culture, Kristofferson left the Army in 1965 to bravely pursue songwriting in Nashville – a decision that caused his family to disown him. The scholarly Oxford graduate then took on humble work as a janitor in a recording studio to chase his dreams.
During this period, Kristofferson also worked as a commercial helicopter pilot in the Gulf of Mexico, servicing offshore oil rigs. His experiences among marginalized laborers informed songs vividly capturing their lives. To get Nashville producers to listen to his demos, Kris famously landed a helicopter in Johnny Cash’s yard unannounced. Reluctantly, Cash gave the tapes a chance and immediately loved “Sunday Morning Coming Down,” recording it in 1970 and kickstarting Kristofferson’s career.
Kristofferson’s stellar 1970 debut album earned him massive success and Grammy nominations. More acclaimed records cemented his pioneering status in country and folk music. His introspective storytelling helped develop the raw “outlaw country” sound.
Beyond music, Kris flourished as an actor, winning a Golden Globe starring opposite Barbra Streisand in the 1976 remake of A Star Is Born. On screen and off, he lived an adventurous life using his helicopter skills for daring rescues while also passionately supporting global human rights struggles.
In 1985, Kristofferson joined fellow legends Johnny Cash, Waylon Jennings, and Willie Nelson to form the supergroup The Highwaymen. Their single “Highwayman” won Single of the Year from the ACM Awards. To date, Kristofferson has been inducted into the Songwriters, Country Music, and Nashville Songwriters Halls of Fame.
Now 86, few artists have embodied the restless American spirit like Kris Kristofferson. Raised a scholar and Army captain, he traded it all for music glory. His boldness in bucking expectations to follow his creative passion remains an inspiration.
Kristofferson’s introspective lyrics gave country music a bold new voice through deeply personal storytelling. As one of the pioneers of “outlaw country,” he fearlessly tackled topics like poverty and addiction and moved the genre in a more progressive direction.
The sincerity of Kristofferson’s rugged yet sensitive voice keeps his classic songs timeless. Numbers like “Help Me Make It Through the Night” and “Sunday Morning Coming Down” remain beloved country standards. In fact, over 450 different artists have covered Kristofferson’s prolific catalog of introspective story songs over the decades. His heartfelt music conveys the empathy and humanity behind the words.
In his later years, Kris Kristofferson continues imparting wisdom, even as he confronts health issues. His incredible life story demonstrates how creative determination can transform someone from humble beginnings into a legendary artist who stays true to himself.
Kristofferson has said he would like the first three lines of Leonard Cohen’s “Bird on the Wire” on his tombstone:
“Like a bird on the wire
Like a drunk in a midnight choir
I have tried in my way to be free.”
These lyrics epitomize his spirit of independence and longing for grace. Like his heroes Johnny Cash, Willie Nelson and Janis Joplin, Kristofferson nurtured his gift despite the risks. His bold artistry enlightens music and gives voice to the wild, searching soul.
Stay curious, keep exploring. 😊
I was thinking about... 