“I do not believe that anything has ever come closer to imitating reality.” So wrote Baldassar Castiglione upon first viewing Girolamo Genga’s scenografia (stage setting) for Calandria, the landmark work by Bernardo Dovizi from Bibbiena. These words attest to the innovative push toward realism brought about by commedia erudita (learned comedy) in the sixteenth century. The connection between learned comedy and realism is at the basis of this chapter, which examines the key role played by the learned theatrical productions in establishing new ideas of space and the city through stage setting, and how these new ideas were informed by the technique of perspective developed in the fine arts during the Renaissance. By introducing perspective in stage design, the commedia erudita opened a game of interrelations between texts, visual set, and performance that engaged the viewer in drawing connections between his personal experience and the artificial representation of the city. Beyond drawing these connections, I further argue that the way the city was represented on stage suggests a changed conception of society overall. As the Renaissance court (whether it be a ducal or a prince court, or an oligarchic higher middle class) used learned comedies and art to promote its political and social functions, the use of the city in these performances emphasizes a tension between a search for an ordered and fixed image of the public space and the chaotic and disorderly perception of everyday life.