Hermes on Two Wheels shows the dynamic world of the bicycle messenger through a sociological lens, based on a five-year participant observation study. Beginning with the experiences of messengers themselves and moving to describe the structural settings of those experiences, the research shows how messengers work within a political-economic system that devalues semi-skilled labor and strips people of emotional fulfillment. The voluntary risk-taking of messengers becomes a means of achieving such emotional fulfillment as well as making a living, while their stylistic expressions pay dividends in cultural scrip rather than money. Through their work, messengers help to reproduce and maintain the structures of society while also constructing a vibrant, rebellious, politicized subculture that has come to represent the new urban hipster, an image continually under threat of co-optation.