10. "You Could Drive A Person Crazy"
In some ways, "You Could Drive A Person Crazy" is the quintessential Sondheim song. The music evokes a particular movement in pop culture, perfectly embodying it while simultaneously turning it on its head — in this case the girl groups of the Andrews Sisters era. The lyrics make use of this almost dizzily bouncy, almost deliriously cheerful aesthetic to disarm the listener in a monologue that is first fun, then cutting, and surprisingly vulnerable. Yes, monologue. Sondheim songs, even terrific out-of-context numbers like "You Could Drive A Person Crazy," always function dramatically as words out of the character's mouth.
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