Queer Yiddishkeit—a cluster of works in literature, journalism, filmmaking, and performance art—constitutes one of the most revealing and provocative developments in contemporary Jewish culture. These works all juxtapose queerness and Yiddish in some way and do so as a means of challenging some cultural status quo. Queer Yiddishkeit epitomizes how, a half-century since the Holocaust, cultural engagements with Yiddish have been reconceiving the possibilities of the language and its relationship to culture and peoplehood. Several examples of Queer Yiddish culture are examined herein, especially performances that link Yiddish with drag, focusing on the different ways that they interrelate Yiddishness and queerness. This essay then considers what the practices of Queer Yiddishkeit suggest for the theorizing of Yiddish now, at a crucial juncture in the language's history, marked, on one hand, by the imminent passing of the last speakers who used Yiddish as a vernacular before World War II, and, on the other hand, by the expansion of what the author terms postvernacular engagements with Yiddish.