After nearly 450 years of colonial administration, Portugal returned the territory of Macao to the People's Republic of China in 1999. Following the handover, Macao's postcolonial government dismantled the forty-year-old local gambling monopoly and opened Macao to investment by gaming companies from North America, Australia, and Hong Kong. These companies are collectively spending $25 billion to tap the increasingly affluent and mobile market of tourists just across the border in mainland China. This investment has prompted remarkable economic development in the tiny city as well as a phantasmagoric transformation of the cityscape and a concomitant transmutation of Macao's social landscape. Understanding contemporary Macao requires attending to how the legacies of Portuguese colonialism and fascism and Chinese communism and market socialism merge in the spaces of the city today. Drawing inspiration from Walter Benjamin's dialectical analysis of the obsolete commodities of mass culture, this paper meditates through text and photographs on four copresent moments of Macao - socialist fossil, colonial ruin, capitalist dream, and utopian wish. A form of physiognomic urban 'dream analysis' rescues these multiple contradictory meanings of Macau and investigates the city's crucial role in both China'.s economic reforms and its utopian desires.