This article reports findings from a nationally representative, cross-sectional study of American high school students on the putative influences of work of more than 20 hours per week and adolescents' perceptions of family closeness on school behavior and grades. As previous research has been inconsistent regarding the relations among these variables, participants' self-reported closeness to their family of origin was examined as both a potential mediator and moderator of the relationship between work intensity and school disengagement. Next, work intensity was modeled as a moderator of the relationship between family closeness and concurrent school adjustment. For boys, the family closeness mediational model provided the best fit for the data. For girls, the moderator models provided a significantly better fit. Results imply that indirect models of work intensity, school outcomes, and the influence of the familial context in which adolescents are embedded may best clarify the relations among these variables.