This chapter examines the evolution of the rapper, producer, fashion designer, and reluctant reality television personality Kanye West. An artist whose subject matter addresses personal anxieties and self-doubt in ways seldom seen in mainstream rap, West engages fame and celebrity in conflicting and often incongruous ways. Through the amateur creation and distribution of memes, gifs, hashtags, and other “viral” cultural articles, the public plays an unprecedented role in the construction—and destruction—of celebrity. Exploitation of this process, in which West consciously engages, constitutes a unique enactment of celebrity work. West’s interaction with the notion of celebrity—as an antihero, an activist, and an icon—speaks both to the changing role of hip hop in mainstream American culture and to the ongoing racial microaggressions of “post-race” America toward influential black celebrity.