This is the first article written on the work of Gordon ‘Doc’ Anderson, a self-taught photographer and entrepreneur who shot photographs of Harlem’s famed Apollo Theater between 1949 and 1976. Although Anderson created the largest body of work documenting the theater, he was neither a paid employee of the Apollo nor a member of the press. Instead, he made a living selling commemorative photomontages directly to the Apollo’s visiting performers for a few dollars apiece. The homemade compositions occupy a middle ground between the vernacular snapshot and the mass-mediated image, adapting a graphic treatment of celebrity pictures akin to those found in fan magazines and tabloids. The souvenirs, with their ever-changing configurations, can also be viewed as a kind of musical composition. Anderson’s montages represent his attempt to formulate a commercial response to Harlem’s musical milieu, making images that might look as the Apollo Theater sounded. Combining extensive biographical research with visual analysis, this paper seeks to recover meaning from Anderson’s montages in relation to popular music, celebrity culture and fandom in midcentury Harlem.