In this paper, I propose that virtual worlds, based as they are on game design and architecture, demonstrate a capacity for meaningful experience in the midst of a largely routinized and bureaucratic modernity. I suggest that game-like virtual worlds reveal an aspect of the human condition that has largely been obscured under modern conditions — that of the human engagement with the unpredictable or contingent. Max Weber and his definitive account of bureaucracy and the state formed the backdrop for a century-long inquiry into the vanishing sources of meaning under the advent of rationalization; for Weber, charismatic leadership provided the only answer to the iron cage of rationality. But a consideration of bureaucracy, games, and virtual worlds alongside one another fills in this bleak picture. If bureaucratic projects are driven, at root, by an ethic of necessity (in their procedures and logic of consistency), games, and the virtual worlds based on them, are driven by an antithetical commitment to (contrived) unpredictability. As socially legitimate spaces for cultivating the unexpected, games and their virtual worlds provide grounds for the generation of meaning that is not ultimately charismatic. Virtual worlds like Second Life have largely retained this open-ended quality, and they rely on game architecture to create a domain with wide opportunities for success, failure, and unintended consequences, and it is this that makes possible the emergent effects we witness today. What remains to be considered is the extent to which institutions are beginning to make use of these features of games to develop new means of pursuing their interests.