There's a lot of pathos in this song, as the various characters presented (Lonesome Sue, Jimmy) deal with cheating and heartbreak. The singer finds himself in Jamaica, where he lets it all go.
Bishop didn't write this from personal experience. He told us: "I write from titles usually. I was walking down to the corner grocery store in Silverlake where I was living at the time and I came up with the idea of 'On and On.' My landlady had a lot of exotic flowers all around the house and I wanted to write something from somewhere else like Jamaica." (Thanks to Stephen for the info. Check out his website at stephenbishop.com