In this paper we address five questions. First, how do individual- and labor-market-level factors influence high school students' paid employment behaviors? Second, to what extent is student employment associated with high school dropout net of these factors? Third, does the association between student employment and dropout vary by students' race/ethnicity and other socio-demographic characteristics? Fourth, to what extent do local labor-market opportunities influence high school dropout? Fifth, does the association between student employment and high school dropout vary by local labor-market circumstances? Using data from the National Educational Longitudinal Study of 1988 and the 1990 US Census, we find that several individual- and labor-market-level factors influence students' employment behaviors; that adolescent employment and dropout are strongly associated, even after adjusting for individual- and labor-market-level factors; that this association does not vary by individual-level attributes; and that this association does not vary across labor markets. We end by describing two perspectives on the mechanisms linking adolescent employment and dropout.