Kristofferson scuffled in Music City for four years, working as a commercial chopper pilot and sweeping out Columbia Records’ local studio (where he reputedly first crossed paths with his future “Pat Garrett” co-star Bob Dylan, in town to record “Blonde on Blonde”). It took some convincing to get one of country music’s most prominent performers to pay attention to his songs, in an incident that became a Nashville legend.
Johnny Cash later recalled, “I didn’t really listen to them until one afternoon, he was flying a National Guard helicopter and he landed in my yard. I was taking a nap and June said, ‘Some fool has landed a helicopter in our yard. They used to come from the road. Now they’re coming from the sky!’ And I look up, and here comes Kris out of a helicopter with a beer in one hand and a tape in the other.”
As recorded by Cash, live on “The Johnny Cash Show,” Kristofferson’s “Sunday Morning Coming Down” became one of the writer’s first significant hits, and it was honored as song of the year by the Country Music Assn. He accepted the award in a famously bleary televised appearance.
Now legitimized as one of country’s most distinguished hit-crafting writers – with notable covers by such other top talents as Ray Stevens, Bobby Bare, Roger Miller and Waylon Jennings to his credit – he was signed to Monument in a long-term pact. His 1970 debut LP “Kristofferson” saw meager sales, but it rose to No. 10 on the country charts in 1971 after the label retitled the set “Me and Bobby McGee” in the wake of Joplin’s hit rendition.
A country music outlaw even before the term attained currency, Kristofferson racked up eight consecutive ‘70s albums in the country top 25. His mix of laconic charm and cool danger brought him a run of starring roles in Hollywood vehicles that included “The Sailor Who Fell From Grace With the Sea” and “Semi-Tough.”
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