Three hundred and sixty homeless youth in Toronto, Canada were asked to report how they made money in order to survive. Income generation among this marginal population was conceptualized by fusing theory and research in the fields of the informal economy and the "underclass" and sociological criminology. While economic activity was found to be flexible, our analysis also reveals that work on the street is stratified on the basis of worker backgrounds and job/situational conditions. In terms of policy, our key theme in this paper is that successful strategies to move young people off the streets cannot rest simply on low paying employment as a solution.