For a man who spent more than five decades shaping country music, Kris Kristofferson gave surprisingly harsh advice to anyone dreaming of following in his footsteps.
“Don’t do it.”
In a 1985 interview with a young fan, Kristofferson laughed as he delivered the line — but he wasn’t joking. Beneath the humor was hard-earned truth.
“The only reason to devote yourself to this kind of life is you have no other choice,” he explained. “That you’d be miserable doing anything else.”
Kristofferson knew exactly how difficult the road could be. Before success came, there were years of uncertainty. He left a promising military career, worked odd jobs in Nashville — even as a janitor at Columbia Recording Studios — and endured rejection after rejection before songs like “Sunday Mornin’ Comin’ Down” and “Help Me Make It Through the Night” changed his life.
Even after the hits came, the pressure never eased.
“It’s a risky business,” he warned. “You have to show a lot of yourself. You have to be willing to take rejection, and criticism and abuse.”
That vulnerability defined his songwriting. Kristofferson wrote about loneliness, doubt, faith, failure — subjects that required emotional exposure. But exposure comes at a cost. Fame invites scrutiny. Audiences judge not only the songs, but the person singing them.
“You gotta be real lucky to be able to do it,” he said. And luck, in his mind, was as necessary as talent.
Yet what makes his warning so powerful is that it came from someone who had succeeded beyond measure. Kristofferson wasn’t bitter. He was honest. He had earned Grammy Awards, penned classics recorded by legends, starred in major films, and stood alongside Willie Nelson, Johnny Cash, and Waylon Jennings as part of The Highwaymen. Still, he viewed the business with clear eyes.
He also remained deeply humble about his influence. In interviews from the late 1970s, he deflected praise that labeled him a leader of the outlaw movement. He insisted he had been a fan of Willie, Waylon, and Cash long before anyone knew his name. He even credited Bob Dylan with reshaping Nashville’s image more than he ever did.
“It’s kinda weird for me to try and take credit for helping my heroes,” he once said.
In the end, Kristofferson’s blunt advice wasn’t discouragement.
It was a test.
If you can walk away from the dream, he implied, you probably should. But if you can’t — if music is the only thing that makes sense — then you might be built for it.
Because for Kris Kristofferson, the only reason to chase the stage…
Was that he simply had no other choice.