This article provides a historical overview of the development of urban, location-based, and hybrid-reality mobile games. It investigates the extent to which urban spaces have been used as playful spaces prior to the advent of mobile technologies to show how the concept of play has been enacted in urban spaces through three historical tropes of urbanity: first, the transformation of Baudelaire’s flâneur into what Robert Luke (2006) calls the “phoneur”; second, the idea of dérive as used by situationist Guy Débord; and last, the wall subculture called parkour. The authors present a classification of the major types of mobile games to date, addressing how they reenact this older meaning of play apparent within these former tropes of urbanity. With this approach, they hope to address two weaknesses in the current scholarship—namely, differentiating among a range of types of games mediated by mobile technologies and assessing the important effects of playful activities.