The Many Lives of Kris Kristofferson

Rhodes Scholar, Boxer, Helicopter Pilot, Actor, Hall of Fame Musician, and that’s just scratching the surface.

Jeff Cunningham
3 min readFeb 6, 2024

The story of the legendary Kris Kristofferson is punctuated with expressions like “no ways,” “seriously,” and “you’ve gotta hear this.”

So, let’s dive into the whirlwind of a man who’s lived several lifetimes in one.

Born to a military family on June 22, 1936, in Brownsville, Texas, Kris became the ultimate nomad, as his father moved from town to town until the family settled in sunny San Mateo, California. There, he transformed into the quintessential brainiac, bagging essay prizes and getting his mind stretched at Pomona College, where he became a Golden Gloves boxer and a rugby player.

Every year, Oxford chooses 32 of the most promising of America’s college graduates to become Rhodes Scholars. This list includes Bill Clinton, Ronan Farrow, Susan Rice, George Stephanopoulos, and in 1958, Kris Kristofferson. He studied at Merton College and in his spare time was awarded a Blue for boxing, played rugby, and began writing songs. Okay, he got lucky, right?

Kristofferson in U.S. Army Ranger School

Before fame and the footlights became his gig, Kris took off to the skies as a helicopter-flying Army captain. The Army preferred that he teach English at West Point. A short while later, he pulled a U-turn toward Nashville with guitar strings. The family was not throwing a party.

Kris flew commercial helicopter work to pay the bills and became a janitor at a Nashville studio. His night job put him in contact with Johnny Cash, who was not interested in the sweeper’s singing — until Kris landed a helicopter in Cash’s backyard.

Cash eventually recorded Kristofferson’s stirring hangover hymn, “Sunday Morning Coming Down.” It hit №1, crossed over to the pop chart, and won the Country Music Association’s Song of the Year Award in 1970.

“I pitched John every song I wrote when I was working as a janitor, and he was real supportive but never cut anything,” Kristofferson said when called at his Hawaii home. “When he cut that, he blew me away. It became a record of the year, and I never had to go to work again.” Cash also got Kristofferson to open for him at the Newport Folk Festival 1969.

“That started my whole performing career,” said Kristofferson.

Soon enough, Kris was crafting classics like “Me and Bobby McGee,” serenading his way into Janis Joplin’s heart.

Flash forward to 1985, and Kris is shoulder to shoulder with the country’s finest rebels — Waylon, Willie, and Johnny — as The Highwaymen. Together, they redefined Nashville, proving that country could rock just as hard as any genre.

But why stop at music? Kris dove headfirst into acting, snagging roles as outlaws, lovers, heroes, and even slayers of the undead in movies like “Pat Garrett & Billy the Kid,” “A Star Is Born,” and those kick-ass “Blade” movies.mY person favorite, a Steven Seagal movie, Fire Down Below.

And yes, he snagged a Golden Globe because, of course, he’s Kris.

Finally, 2004 rolled around, and boom, the Country Music Hall of Fame. Because when you’re Kris Kristofferson, legends are for Tuesday.

So, there you have it — the whirlwind saga of Kris Kristofferson, a man who’s defined every label but remains undefinable.

Kristofferson has said that 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