Robert Venturi’s Complexity and Contradiction in Architecture of 1966 is an architectural, not an urban book. Its compositional principles and analysis focus on individual buildings, with the city in only a minor role. Yet urbanism was a central theme in Venturi’s second book, Learning from Las Vegas, co-authored with Denise Scott Brown and Steven Izenour in 1972. Moreover, Complexity and Contradiction originated as an urban study. Its genesis was Venturi’s proposal for an American Academy Rome Prize, refined in three applications from 1952–54, all on urbanism. Was Venturi’s first book merely a detour from his early urban interests, which re-emerged later? Or does it sublimate ideas about the wider built environment? His well-known interest in Townscape during the 1950s shaped his early research into context and two early essays, one on the Campidoglio’s surroundings in Rome, and another on Frank Lloyd Wright’s integration of buildings and landscape. This research remained at the core of Complexity and Contradiction. Although the book pulls architectural issues into the foreground, “crypto-urban” themes connect it to ideas about how to see and experience the broader built environment.