I consider Paul Simon one of the best rock guitarists and songwriters of his generation. I have been learning the guitar for about forty years with little progress to show but I keep trying and the Simon and Garfunkel oeuvre is what I often work on, especially the song Mrs. Robinson from the film The Graduate.
The lyrics of his songs abound in non-sequiturs and can take weird turns. In this 1970 interview with Dick Cavett, Simon explains that he writes lyrics in a stream of consciousness mode, putting down whatever comes into his head at that moment, with only a minor effort at producing a coherent narrative, hoping that some meaning will emerge later. He gives Mrs. Robinson and the cryptic line about Joe DiMaggio as an example of how he writes.
Here is the full song performed live for those not familiar with it.