For country music fans there are few names that so completely embody the Country and Western genre as Kris Kristofferson.
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Rolling Stone called him “one of America’s finest songwriters.”
“Kris Kristofferson ruined my education” Turk Pipkin wrote proudly in Esquire in 2014.
Kristofferson trained as a Ranger and a helicopter pilot, eventually reaching the rank of Captain while stationed in Germany. But then he received orders to West Point to teach English.
A Rhodes Scholar educated at Oxford, Kristofferson was more interested in creative writing and music than the military, so, rather than accept orders to West Point, Kristofferson chose to leave the Army.
The move allegedly caused his family to sever ties with him, and he is rumored to not have spoken to his mother for over twenty years as a result.
Leaving the Army did not immediately pay off for Kristofferson. He found himself struggling to make ends meet in Nashville and working as a janitor at a recording studio. It was there that Kristofferson first came across June Cash. He gave her a demo tape and asked her to pass it on to Johnny Cash, which she did…but the tape went unheard.
Kristofferson, struggling to support his growing family, then briefly served in the Tennessee National Guard.
That’s when Kristofferson did something that would land most service members today in the brig:
He stole a helicopter.
“I flew in to John’s property,” Kristofferson recalls. “I almost landed on his roof.”
The country music legends Kris Kristofferson (left) and Lyle Lovett (right) performed in the East Room of The White House for D.C. schoolchildren on Nov. 22, 2011. (Image by Flickr user John Arundel | (CC BY-NC 2.0)
Kristofferson notes that he was lucky Johnny Cash didn’t shoot down the old helicopter with his shotgun.
The risk payed off, though, as Johnny Cash wound up recording the song Kristofferson was trying to get him to listen to: “Sunday Morning Coming Down.” That recording “lifted me out of obscurity,” Kristofferson admits.
Cash was a fan of Kristofferson’s bravado, and the two would go on to work together many times. With publicity help from Cash, Kristofferson penned dozens of hits, including “Vietnam Blues,” “Help Me Make it Through the Night,” and “Me and Bobby McGee.” Together with Willie Nelson and Waylon Jennings, Cash and Kristofferson completed the group “Highwaymen.”
Kristofferson wrote songs for the likes of Waylon Jennings, Jerry Lee Lewis, Johnny Cash, Sammi Smith, Ray Price, and Janis Joplin (with whom he had a brief relationship before her death).
(Johnny Cash & Kris Kristofferson — “Sunday Morning Coming Down” | YouTube)
His bravado served him well on screen, too, and Kristofferson has enjoyed a long running acting career in addition to his music career.
He appeared with Wesley Snipes in the “Blade” movies and even had a song on “Grand Theft Auto.” Kristofferson worked alongside Martin Scorsese, starring in “Alice Doesn’t Live Here Anymore,” and with Barbra Streisand in “A Star is Born,” for which he won a Golden Globe for Best Actor.
Kristofferson went on to work with Matthew McConaughey, Mel Gibson, and Tim Burton.
In 2014, Kristofferson received a Lifetime Achievement Grammy Award to go along with his many awards, gold records, and top 40 hits.
Also in 2014, Kristofferson’s son, Jesse Kristofferson, enlisted in the Coast Guard.
To think, it all happened because he bucked his family military tradition, got disowned, and stole a military helicopter.