Paul Simon started recording this song when he went to South Africa in 1985. He had been listening to a bootleg tape of music from the country, and wanted those sounds for his Graceland album. He recorded with dozens of musicians in his 17 days there, and he had a great experience with members of a popular South African group called Stimela - drummer Isaac Mtshali and guitarist Ray Phiri. When Simon returned to America, Mtshali and Phiri joined him for more recording sessions (this time at The Hit Factory studios) and a Saturday Night Live appearance. Bits of the South African sessions were edited together with the New York recordings to complete the track. Simon says that the song ended up sounding more like the music of Malawi and Zimbabwe, rather than South Africa.
Paul Simon isn't big on political lyrics, so despite the myriad political issues he saw in South Africa, he wrote lyrics for the Graceland tracks that told little stories (this one about a love gone bad), and more importantly, matched the music. This wasn't easy, and Simon became frustrated when he couldn't get the lyrics to fit. The breakthrough came when he listened to the tracks again. In the Under African Skies documentary, he said, "I realized that the guitar part was playing a different symmetry than I assumed, and the bass was doing something that was much more important, and I might be better off following what the bass was doing. I started thinking about the lyrics and what effect that would have on storytelling, and I began to raise the bar on my own writing."
As Simon explained in an interview with SongTalk magazine, there are two reasons for the "Vol. II" in the title. One is that Simon wanted to differentiate his "Crazy Love" from the Van Morrison song of the same name. The other is that he is talking about a love that has started and stopped more than once.
The same guy who played the pennywhistle on "You Can Call Me Al
" played soprano saxophone on this song. His name is Morris Goldberg, and he's a white South African who had moved to New York.
The opening line mentions Fat Charlie the Archangel. This character came completely out of nowhere. Says Simon: "It doesn't represent anyone."