The era name "Kansei" meant "lenient rule." Paradoxically, however, the Kansei era (1789-1801) was marked by a series of strict moral and economic reforms. Through these restrictions, the Tokugawa shogunate sought to restore its authoritative image and clamp down on the decadence and unruliness of the bourgeoisie chōnin (townspeople). In particular, prohibitions were aimed at the chōnin cultural art of ukiyo-e woodblock prints. These images embodied the Edo aesthetic of ukiyo (the Floating World) with its pleasure-seeking entertainments, fashionable tastes, and passion for spectacle. I look at the prints of Kitagawa Utamaro (1753-1806), renown as the connoisseur of women, and examine how prohibitions served to increase the creativity of Utamaro and fellow artists/literati. By adopting the practice of mitate, loosely defined as parody, Utamaro created layers of meanings in his artwork that both celebrated chōnin culture and covertly refuted the shogunate's Confucian ideology through inverted political structures. Edoites love for play and taste for the fantastical and erotic allowed Utamaro and other artists to develop prints with coded interpretations only intelligible to their chōnin clientele. The conflict between the shogunate's aspirations for a well-ordered society and the urbane realm of the chōnin sets up the fault line which Utamaro cleverly exploits in his prints. Building on Mikhail Bakhtin's idea of carnival and post-modern "safety-valve" theories, I argue in this thesis that Kitagawa Utamaro uses the art of spectacle and literary appropriations to negotiate shogunal powers. I will not only examine political imagery, but reinvented allusions to classical texts (mitate) and popular forms of theatricality (kabuki and bunraku puppet theater) as well. Utamaro's utilization of popular literary and theatrical tragic love, particularly giri-ninjō (the conflict between one's duty to society and one's true feelings), suggests resistance to the shogunate's attempt to rein in the chōnin and systematize the human experience.