Since the mid-1970s, the emigration of Jewish-Israelis to overseas destinations has become a recurring issue of acrimonious discussion and debate in the Israeli public sphere. This article traces historical anxieties about emigration, provides political frameworks for understanding related discussions and debates, and examines their popular cultural expressions. By analyzing three songs performed by Israeli singers Arik Einstein, Oshik Levi, and the indie group Shmemel, the historical, political, economic, and cultural elements of this debate are situated and explored. We argue that these songs reflect elements of the public debate about the angst of the Israeli, sabra, Ashkenazi middle-class émigré.