Stephen Sondheim proved that musical theater could adapt to any era. A favorite composer and lyricist of those suspicious of melodrama—and of musicals in general—the native New Yorker brought a revolutionary's spirit to Broadway, and his stylistic daring left an unmistakable stamp on everyone from Lin-Manuel Miranda to indie-pop maestro Stephin Merritt. Sondheim grew up studying the Great American Songbook masters, learning their seat-filling tricks as a precocious theater-goer in the '40s, but he was already yearning to push into new political, musical, and emotional territory when he made his own debut in the '50s. His lyrics smuggled the social dramas of the day into seemingly escapist entertainment (West Side Story), merging the slang-infused wit of city life with a love of finely wrought poetry. He had a range like no one else; his shows could be formally audacious (Assassins), emotionally wrenching (Company), or uproariously farcical (A Funny Thing Happened on the Way to the Forum), yet his melodies were both instantly memorable and subtly radical. And his sophisticated modern standards, like "Send in the Clowns,” reached far outside Broadway’s orbit, having been endlessly reinterpreted by rockers, folkies, and soul singers. The key to his success? As Sondheim told Miranda when he was workshopping Hamilton: “Variety, variety, variety, Lin. Don’t let up for a second. Surprise us." Sondheim died on November 26, 2021, at the age of 91.