Kris Kristofferson: The Incredible Life Of Country Music’s Most Interesting Man

Kris Kristofferson country music singer
Rick Diamond/Getty Images

If I was to blindly give you the following resume that someone racked up by the age of 30, what career do you think its owner would have chosen?

Rhodes Scholar, award winning essayist, three sport letterman in college, Golden Gloves boxer, cadet commander of ROTC, sports editor of a newspaper, helicopter pilot, Army Ranger, dredging contractor, and even… record label janitor?

Truthfully, the list would be endless, as they could have pursued any number of careers, including professional athlete, ranking military officer, journalist, novelist, corporate executive, heck it’s almost not worth trying to figure out all the possibilities that come with being a Rhodes scholar alone.

But what about country music singer/songwriter?

As strange as it may seem, that’s exactly what the person in question chose to do with his life, leaving all of those opportunities, including an offer to teach at West Point, to chase a dream.

Kris Kristofferson is truly a once in a lifetime character whose elaborate backstory adds to the already enormous legacy he built in the country music world.

Born to a military family in 1936, his first dream in life was to be a writer, which seems like it would have been a viable path, as two of his earliest stories, “The Rock” and “Gone Are The Days” won some awards and were published in the prestigious The Atlantic Monthly. 

After graduating high school, he enrolled at Pomona College to further pursue his writing aspirations. There he racked up a ton of achievements, including membership in the senior honor society, Cadet Commander of the school’s ROTC program, sports editor of the school newspaper, excellence in three varsity sports (football, rugby, and track and field), became a Golden Gloves boxer, and as a very big cherry on top, was selected as a Rhodes Scholar, one of just 32 American’s invited to study at the iconic Oxford University in England that year.

He was profiled in Sports Illustrated for these accomplishments in 1958 as part of their Faces In The Crowd series.

Certainly makes my college resume look pretty puny…

He continued his pursuit of excellence while at Oxford, earning a “Blue” in boxing (the highest athletic honor one can achieve), continued his rugby career, and began writing songs. He graduated in 1960 with a Bachelors in Philosophy.

But he didn’t rest upon leaving Oxford.

He felt pressure from his family to continue their tradition of military service, so he joined the US Army, where he eventually earned the rank of captain. During his time, he became a helicopter pilot and completed one of the hardest programs in the entire military, Ranger School. He was then stationed in West Germany, where he formed a band.

Despite the incredible success he had in the military, he never quite felt at home. After his deployment, he was offered a teaching job at West Point (yet another phenomenal opportunity), but turned it down to chase what he now knew his passion was: Music.

He moved to Nashville, Tennessee, in 1965, a move that caused his family to disown him and it’s not clear if they ever fully reconciled.

He took a job as a janitor at Columbia Recording Studios, where he happened to met June Carter and gave her a demo tape to give her husband, Johnny Cash. Kris then landed a helicopter in Johnny’s yard to give him another demo. While nothing came of it at first, we know that Johnny eventually refused to record until Kris was allowed to sit in on the session, and the rest, as they say… is history.

Throw in a handful of appearances as an actor and man, what a life Kris lived.

Just goes to show you, no matter what other skills and talents a person may have, they don’t mean a thing unless you have the passion to back it up.

While it certainly was risky to throw away all he had earned before that, safe to say, he made the right decision.

“Sunday Morning Coming Down”

A beer bottle on a dock



A beer bottle on a dock