Adolescent employment during high school has become the norm in the United States, but studies of associated outcomes have yielded mixed results. These discrepant findings may be partly attributable to study methods, including differences in how adolescent employment is measured and how selection factors are taken into account. The present study, based on data from the Child Development Supplement of the Panel Study of Income Dynamics, aims to continue untangling these complexities by (a) examining whether the strength of theoretical predictors varies when predictors are assessed in a comprehensive model that simultaneously controls several psychological, family, and community factors; (b) determining whether the strength of predictors varies depending on how adolescent employment is measured (work status, work duration, and work intensity); and (c) assessing whether race moderates some of these relationships. Results indicate differences in how each predictor is related to each dimension of adolescent employment, as well as a moderating effect of race on the relationship between educational expectations and number of hours adolescents worked each week.