Mrs. Robinson (The Graduate)

The acoustic guitar enters with a kind of practiced casualness, all nimble fingerpicking and easy momentum, and Paul Simon's voice follows with the same quality — conversational, unhurried, as if the song is simply continuing a conversation already in progress. But beneath that breezy surface "Mrs. Robinson" is doing something fairly savage: using the syntax of a folk-pop song to anatomize an entire civilization's disillusionment. The song arrived in the context of The Graduate, a film about a young man seduced by and drowning in exactly the suburban prosperity that was supposed to represent American success, and Simon and Garfunkel understood the assignment completely. The "Jesus loves you" refrain lands with layered irony — simultaneously sincere, absurd, and deeply sad, suggesting a culture that has maintained the language of its values while hollowing out their content. The production is lively and propulsive, which is part of the trick: the critique slips in through a song that sounds like it's just having fun. Culturally it stands as one of the more precise documents of the late-sixties moment when optimism and disillusionment first started openly cohabiting. It's a song for watching the world from a distance and feeling simultaneously amused and bereft.