The Smilin' Buddha Cabaret operated at 109 East Hastings Street in Vancouver's Downtown Eastside (DTES) neighbourhood from 1952 until the late 1980s. Over its forty year history, this club hosted variety shows, striptease dancers, and musicians from the city's jazz, rhythm and blues, and punk rock music scenes. Today, the building that was home to the Smilin' Buddha sits in the middle of a neighbourhood undergoing a contested transformation as new upscale develops redefine the historically low-income, working-class neighbourhood. At the same time, the club is being creatively reinterpreted as a symbol of the city's postwar prosperity and rich entertainment history where it was once described primarily as a skid row dive bar. This thesis traces the changes through the history of the Smilin' Buddha to understand how the club and its entertainment evolved in relation and in opposition to the development of the neighbourhood's built environment, geography, and identity. Through this, I argue that the development of the Smilin' Buddha and the wider DTES has never been the result of natural market forces; instead, it has always been a site of negotiation and contestation among multiple overlapping interests who do not have equal access to power. At the same time, it has been a site of cultural vitality, even if it has not been a site of economic vitality.