This study examined relationships among gender, perceived parental monitoring, externalizing behaviors, and adolescent alcohol use in a 2-wave longitudinal study. Females reported more perceived parental monitoring and less alcohol use than males. Perceived maternal and paternal monitoring were related to less alcohol use over time. Increases in alcohol use were associated with increases in externalizing behaviors over time. Perceived maternal monitoring mediated the relationship between gender and youth drinking and was also a significant predictor of changes in adolescent drinking over time. Perceived paternal monitoring was not a predictor of adolescent drinking in the context of perceived maternal monitoring and externalizing behaviors. The importance of gender in implementation of prevention programs is discussed.