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This article presents the results of an investigation of the following questions: How do low-income African American and Latino youths negotiate the boundaries between school and peer group contexts? Do variable forms of negotiation exist? If so, what are they, and how do they manifest? In addressing these questions, the author posits two arguments that directly challenge the “acting white” thesis. The first is that black and Latino students' academic, cultural, psychological, and social experiences are heterogeneous. This article examines three groups of low-income African American and Latino students who differ in how they believe group members should behave culturally—the cultural mainstreamers, the cultural straddlers, and the noncompliant believers. Second, this article returns to the sociological signification of four dimensions of the phenomenon of (resistance to) acting white and highlights the varied responses of the three groups to the social boundaries that collective identities engender and that status hierarchies in schools produce. Straddlers appear to traverse the boundaries between their ethnic peer groups and school environments best. The analyses are based on a combination of survey and qualitative data that were collected from a series of in-depth individual and group interviews with an interethnic, mixed-gender sample of 68 low-income, African American and Latino youths, aged 13–20.