Storytelling has a strong tradition in inner-city American communities. In this article, we examine patterns of storytelling among a sample of drug-using women from New York City who engage in street-based sex work. We consider two particular formats of storytelling for analysis: “street smarts” and “urban myths.” Street smarts are stories of survival, and urban myths are compilations of street legends spread by word of mouth. The narratives are filled with tales of extreme risk across situations. The women used the stories to delineate the boundaries of risk as well as to rationalize risks they deemed to be inevitable but temporary in their lives. Few of the women capitalized on the greater instructive quality of the stories toward increased risk reduction, which may relate to the women’s distance from an identity of “sex worker.” If properly harnessed, the strength of storytelling suggests new avenues for risk-reduction interventions.