He was a Golden Gloves boxer.
The Golden Gloves meant that Kristofferson was a talented amateur boxer. But to add to his tough-as-nails persona, he also was skilled at rugby and track, and was even featured in Sports Illustrated for his natural talent playing American football.
He was a Rhodes Scholar.
While studying literature at Pomona College in California, he was selected for a Rhodes scholarship to study literature at Merton College. While there, he continued boxing, performing at the highest levels. Remember: there’s no shame in getting knocked out by Kris Kristofferson. It doesn’t matter if he’s 18-years-old or 81-years-old.
He earned a Ranger tab.
Kristofferson goes Airborne.
The younger Kristofferson was the son of an Army Air Forces officer who went into the service himself as an officer. He was a helicopter pilot who also finished Ranger training and Airborne school. He opted to get out of the Army in lieu of taking an assignment to teach at West Point.
He moonlighted as a janitor… while working on oil rigs.
Kristofferson would sit on oil rigs, flying workers around in Louisiana one week. Then the next week he would moonlight as a janitor in Nashville recording studios so he could drop demo tapes on unsuspecting country music artists like June and Johnny Cash.
In one interview, he recommended having patience if you’re pursuing a career as an artist. Sweeping floors at age 30 might not seem glamorous for a former Army Ranger officer, but ask Kris Kristofferson if it was worth it.
He landed a helicopter on Johnny Cash’s lawn.
The oft-told tale is true: Kristofferson really did land a helicopter on the Man in Black’s lawn. He was trying to get Cash’s attention so Cash would give that demo a listen. What isn’t true is that Kristofferson wasn’t actually drinking a beer at the time… and Cash wasn’t even home.
Unfortunately his boozing is what led to him no longer working the controls of helicopters.
All that and he fought forest fires.
One of Kristofferson’s most often-offered pieces of advice is writing from your own experience. As if football, rugby, being an Airborne Ranger, and working on oil rigs weren’t manly enough, he also worked in construction and fought wild fires in Alaska.