Eminem's emergence as one of the most popular rap stars of 2000 raised numerous questions about the evolving meaning of whiteness in U.S. society. Comparing The Slim Shady LP (1999) with his relatively unknown and commercially unsuccessful first album, Infinite (1996), reveals that instead of transcending racial boundaries as some critics have suggested, Eminem negotiated them in ways that made sense to his target audiences. In particular, Eminem's influential single “My Name Is,” which helped launch his mainstream career, parodied various representations of whiteness to help counter charges that the white rapper lacked authenticity or was simply stealing black culture. This “rearticulation” of whiteness in hip hop paralleled a number of other ideological realignments in the 1990s, many of which pit questions of class against those of race in the service of constructing new political and cultural authenticities. Eminem's performances provide us with a mirror in which numerous questions surrounding whiteness's significance come into focus.