Wordplay is never just a pyrotechnic aftereffect in Sondheim’s shows—it’s foundational, crucial to the plot and the characters’ emotional development. And his work continually reminds you that playfulness (in poetry, in music, in lyrics, in visual art) can be most essential when the subject is deadly serious. Sondheim includes a multiple-choice quiz in a love song—“Now/Later/Soon” from A Little Night Music: “(A) I could ravish her / (B) I could nap”—and likewise in a paean to the uses of a gun, sung from the rotating points of view of the actual and would-be assassins of U.S. presidents: “Remove a scoundrel / Unite a party / Preserve the Union / Promote the sales of my book.”
Of course, as Sondheim often pointed out, he studied under the wondrously kind Oscar Hammerstein II, whose son was his best friend at the George School. Hammerstein was to all intents and purposes Sondheim’s surrogate father.