Songfacts®:

• Ostensibly about Kristofferson's folk-singing friend Ramblin' Jack Elliott, Kristofferson approached the song as something of a self-penned co-write, inspired and begun by his younger self and finished in the present and mortal day. "Ramblin' Jack's one of those people whose whole life was music," he said. "He's like William Blake and Bob Dylan and other people who just believed and lived for whatever poetry they could come up with. That's probably the thing I was trying to be."
  
  Ramblin' Jack Elliott (b 1931) is an American folk singer and performer whose guitar and his mastery of Woody Guthrie's material had a big impact on the young Bob Dylan when he lived in Minneapolis. When he reached New York, Dylan was sometimes referred to as the 'son' of Jack Elliott, because Elliott had a way of introducing Dylan's songs with the words: "Here's a song from my son, Bob Dylan."
  
  Elliott's album, South Coast, won him his first and only Grammy Award for Best Traditional Folk Album in 1996.
• Asked by CMT News how much the man he describe in this song is himself, Kristofferson replied: "I was writing about Ramblin' Jack, but it was the same as when I was writing (The Silver Tongued Devil track) 'The Pilgrim (Chapter 33).' I was writing about Chris Gantry and other people, but I was really writing about me, too, I guess. People thought I was writing about myself. I think we all just have something in common. We're people who are singers and songwriters, and that's just what they are, and it's not contrived or put on. It's the real thing."