Kristofferson had already spent several modestly successful years in Music City’s song mills by the time he broke through as the author of such No. 1 country hits as “For the Good Times” (Ray Price, 1970), “Sunday Morning Coming Down” (Johnny Cash, 1970) and “Help Me Make It Through the Night” (Sammi Smith, 1971). His song “Me and Bobby McGee” became a posthumous No. 1 pop hit for his former paramour Janis Joplin in 1971.
His first four albums for Monument Records, which showcased his rough, unmannered singing and poetically crafted, proto-outlaw country songs, all reached the country top 10, and 1972’s “Jesus Was a Capricorn,” which contained his No. 1 country hit “Why Me,” topped the country LP chart. He won three Grammys: for best country song (“Help Me Make It Through the Night”) and a pair of duets with Rita Coolidge, to whom he was married from 1973-80.
Bill C. Malone noted in “Country Music, U.S.A.,” the standard history of the genre, “Kristofferson’s lyrics spoke often of loneliness, alienation and pain, but they also celebrated freedom and honest relationships, and in intimate, sensuous language that had been rare to country music.”
Kristofferson could be the first to knock his own voice. “I don’t think I’m that good a singer,” he said in a 2016 Rolling Stone interview. “I can’t think of a song that I’ve written that I don’t like the way somebody else sings it better.” But with many of his signature songs, fans would not have wanted them channeled through any other voice, least of all one that smoothed out their raw sentiments.
