By the 1830s, the urban renewal project discussed in the previous chapter only further revealed the intractable messiness of the urban landscape. A decade of gentrification exacerbated anxiety about whether the city’s sites and edifices could compete with surrounding topographical and human congestion. The champions of improvement sought to ease their doubts by commissioning images that abstracted, obscured, or shrank into insignificance the disorder surrounding urban landmarks. Yet even as these ideal representations of the city proliferated, Bostonians questioned whether their fellow spectators saw moral landmarks as intended. A middle-class culture of novels, guidebooks, periodicals, plays, and other sources introduced a new typology of spectators—the connoisseur and the poseur, the vista seeker and the speculator, the libertine and the sentimentalist—who revealed their true characters through their divergent reactions to the city’s monuments, parks, galleries, paintings, and sculptures.