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Written by Kris Kristofferson and first recorded by Roger Miller. Fred Foster shares the writing credit, as Kristofferson wrote the song based on a suggestion from Foster. Roger Miller was the first artist to have a hit with the song, peaking with it at No. 12 on the US country chart in 1969.
Gordon Lightfoot's version hit No. 13 on the pop chart and No. 1 country in his native Canada in 1970, and was also a top 10 hit in South Africa in 1971. Lightfoot sang the song after a detailed tribute to Kris Kristofferson in a CBC broadcast from the summer 1969 Charlottetown Festival.
Joplin also covered the song for inclusion on her Pearl album only a few days before her death in October 1970. Kristofferson had sung the song for her, and singer Bob Neuwirth taught it to her. Kristofferson did not know she had covered it until after her death. The first time he heard her recording of it was the day after she died. Janis Joplin topped the U.S. singles chart with the song in 1971 after her death, making the song the second posthumous number-one single in U.S. chart history after "(Sittin' On) The Dock of the Bay" by Otis Redding.