Academic failure and drinking are both problematic aspects of the adolescent stage of the life course, and the connection between these two behaviors can disrupt the basic functioning of individuals and schools. Drawing on theories of problem behavior from multiple disciplines, this study attempted to determine whether academic failure was a risk factor for adolescent drinking, and vice versa, and then to identify the mechanisms underlying these two longitudinal associations. Cross-lagged models of data from 11,927 middle school and high school students in the National Longitudinal Study of Adolescent Health revealed that the number of classes failed in one year predicted alcohol use a year later more than early alcohol use predicted later class failures. Aspects of social bonding (e.g., attachments to adults) and symptoms of general maladjustment (e.g., delinquency) did more than opportunity structures (e.g., peer norms) to explain the connection between these two behaviors over one year of secondary school.