Six weeks of field research on 14 poor youth who sell services or products on the opulent Paulista Avenue in Sao Paulo, Brazil, explored their work, play, aspirations and childhood outcomes. Comparing the 12 younger children to the two older youth workers who supervised them and to the few Brazilian longitudinal accounts of street youth, the authors seek to understand the longer-term prospects for young street workers. Placing the findings within two dominant theoretical contexts - the study of children's daily interactions, emphasizing their role as agents, and a structural sociology of childhood - the research joins those who combine these perspectives for an understanding of poor youths' childhoods and childhood outcomes in urban Brazil.