The most clever thing about the song is that the chorus—with its plan/Stan, coy/Roy, bus/Gus nursery school rhyming—isn't the real hook of the song; it's session drummer Steve Gadd's marching pattern on his snare against the time-keeping hi-hat/tambourine and syncopated kick drum. That funky drum pattern was what always captured my ear as a kid every time the song came on the radio, often prompting me to go marching around our living room.
The icing on the cake is Simon's intricate chord changes in the verse. The melody skirts the line between the melancholy of an Eastern European folk tune and the soulful, blue melodicism of cool jazz. In fact, the chord changes remind me a bit of John Lewis's composition "Django"—an homage to the late Gypsy jazz guitarist Django Reinhardt—as first recorded by the Modern Jazz Quartet.
Lyrically, "50 Ways..." is a snapshot of a man who's having an affair. He's discussing ideas with his girlfriend—who almost takes on a kind of psychiatrist/analyst role to Simon's patient—about how to ditch his other lover.
Only in recent years did I really get to thinking about the structure of the song—the weighty, emotional subject matter of the verses juxtaposed with the kiddie rhyming in the chorus. It seems to suggest that, here are two adults, engaged in very adult matters, who aren't really thinking things through. They're feigning a clinical and logical approach to solving the "problem." However, they're really acting like little children, having their fun without really considering the consequences.
Pretty smart on Simon's part.
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