Although adolescents in poor urban areas often assume independent, adult-like roles, relatively little is known about the relationship between these roles and other adolescent behaviors. This research examines the association between independent roles occurring within different contexts (e.g. family, peer, work) and aggressive behavior among 516 low-income, urban middle school students. Overall, adolescent employment is related to increases in aggressive behavior. However, associations that familial and peer independent roles have with aggression differ by the extent of youth involvement in paid work. Greater engagement in familial independent roles is associated with decreased aggression among employed adolescents, but with increased aggression among unemployed youth. Also, peer independent roles are related to significantly greater increases in aggression among unemployed, compared with employed, adolescents.