Kris Kristofferson originally wrote this in the 1960s with the late Shel Silverstein when he was a struggling musician with a helicopter pilot sideline job. "I probably wrote more with Shel than anybody," he recalled to CMT News. "I didn't co-write much and not much even with Shel. He'd give me the idea for a song, and I'd go down to the Gulf of Mexico, where I was flying every other week, and try to work on the song. Then we'd come back, and I remember laughing about it. Shel had even convinced himself that he co-wrote the song, but actually I'd written the whole song. He'd given me the idea for it. But we did co-write some songs together."

Country vocalist Connie Smith originally cut this tune for her 1967 album Downtown Country.

Regarding the writing of the song, Kristofferson recalled to CMT News: "I was just writing about heartbreak that I was going through and doing it the way the people I admired like Hank Williams would've handled it."