A number of studies have revealed that low birth weight children have a heightened risk of various maladaptive outcomes, including academic challenges and delinquent involvement. However, very little research to date has examined whether the relationship between low birth weight, poor academic performance, and delinquent peer affiliation is moderated by genetic risk. Using data from the National Longitudinal study of Adolescent Health, the present study examines whether male adolescents born at very low birth weights are significantly predisposed to poor academic performance and delinquent peer affiliation. Moreover, we test whether the effect of birth weight on these outcomes is conditioned by level of genetic risk. We find no evidence that very low birth weight males are more likely to affiliate with delinquent peers or perform poorly in school during adolescence. However, upon examining gene–environment interactions, we find that being born at a very low birth weight does significantly increase the odds of poor academic performance and delinquent peer affiliation among males who possess a higher level of genetic risk. Limitations are noted and the implications of the findings are discussed.