This paper focuses on the musical discourse of nostalgia evidenced in the songs of Dana International, an Israeli transsexual singer who took First Prize in the 1998 Eurovision Song Contest. It is organised around several songs featuring various compositional strategies, beginning with remakes of older songs and leading into new ones. Through quotation of music and/or lyrics, and the alteration and departure from the original, Dana premiers, transforms and renews songs in a way unique to her: she forces the audience to rethink what is natural and what is historically constructed, blurs distinctions between the sexes, past and present, the national and international, and draws on nostalgia as a powerful device to unsettle and question received truths. Her songs often mock and parody the masculinist, nationalist myths of mainstream Israeli culture, exposing the ideology of its artefacts. By promoting various types of blending, Dana challenges the notion of fixed borders. Despite the musical surface of popular song, which sounds international and without specific identity, the deep structures of these songs are in fact very much about complex questions of identity.