1. "Send In The Clowns"
I hesitated to include "Send In The Clowns" at all, let alone as the #1 Sondheim song, but ultimately I'm paying homage to the fact that on a list of Sondheim songs that work out of context, you can't argue with the track record of "Send In The Clowns." After debuting in A Little Night Music in 1973, "Send In The Clowns" was a legitimate pop hit for both Frank Sinatra and Judy Collins (on the pop charts twice for the latter). The song has been so ubiquitous in popular culture that when Krusty the Clown sang it on "The Simpsons," millions of American school-age children thought not, "What is this strange, sophisticated Sondheim aesthetic unfamiliar to my young ears?" but rather, "Oh, that old chestnut." And the reason is clear. Lots of songwriters go for the jugular for effect, but Sondheim only goes there when it's integral to the story he's telling, and that makes all the difference. The result is heartbreaking.
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