From Tom Paxton's book "The Honor of Your Company", 2000:

One night in 1963 I brought a pocket notebook with me to work at the Gaslight and wrote three lyrics between shows. The first and third lyrics were totally forgettable but the middle one was called "My Rambling Boy", which was quickly shortened to just "Rambling Boy".

I came to realize that in writing this song I was responding to a song I'd been hearing both Dave Van Ronk and Bob Dylan sing - a traditional song called " He Was a Friend of Mine". My words were different, of course, and the tune as well, but the theme was the same.

Phil