How are city and culture—the space of the city and the “mind space” of the cultural artifact— connected or disconnected? Contemporary Macao poetry and installation art demonstrate that not only has local culture continued to thrive despite outside pressures on the city’s regional position (a part of “one China” with a localized function) but that the need to produce a critique of these pressures has itself been productive of a politically interested (and interesting) literary and visual culture—a creative culture that demonstrates an opportunistic ambivalence toward identity options. Macao (a city in southern China and, until 1999, sleepy Portuguese possession) is today undergoing unprecedented development. Since the 2002 “liberalization” of casino licensing, the cityscape has taken a monumental turn, with the addition of a number of remarkable landmarks.Today, Macao is promoted as a tourist destination that offers ultramodern casinos and luxurious hotels as well as World Heritage—listed architecture. In recent years, the people of Macao have sometimes felt themselves the victims of contradictory forms of recolonization—by Beijing on one hand and by Vegas-style casino capitalism on the other. Between these gigantic pincers, what chances of survival have local culture and custom had? This article takes a close look at some contemporary Macao poetry and installation art, dealing with themes of monumentality and their meaning for the “new” Macao.