The dawn of the twenty-first century marked a turning period for American Yiddish culture. The 'Old World' of Yiddish-speaking Eastern Europe was fading from living memory - yet at the same time, Yiddish song enjoyed a renaissance of creative interest, both among a younger generation seeking reengagement with the Yiddish language, and, most prominently via the transnational revival of klezmer music. The last quarter of the twentieth century and the early years of the twenty-first saw a steady stream of new songbook publications and recordings in Yiddish - newly composed songs, well-known singers performing nostalgic favourites, American popular songs translated into Yiddish, theatre songs, and even a couple of forays into Yiddish hip hop; musicians meanwhile engaged with discourses of musical revival, post-Holocaust cultural politics, the transformation of language use, radical alterity and a new generation of American Jewish identities. This book explores how Yiddish song became such a potent medium for musical and ideological creativity at the twilight of the twentieth century, presenting an episode in the flowing timeline of a musical repertory - New York at the dawn of the twenty-first century - and outlining some of the trajectories that Yiddish song and its singers have taken to, and beyond, this point.