Working from a life course perspective, this study examined the paradoxical association between academic status and drinking across the transition to young adulthood with multilevel modeling and a nationally representative sample of young people from the Add Health data project (n = 6,308). Taking academically advanced courses in high school was associated with lower rates of current drinking and binge drinking during high school (grades 9-12) but higher rates of both after high school (age range: 20-26). This positive longitudinal association between academic status and drinking was explained partly, but not completely, by educational, family, and work circumstances in young adulthood. The association was less likely to occur among students who attended high schools in which high achievement was the norm. Thus, the association between academic status and drinking behavior reverses across the transition to young adulthood, especially in certain types of peer environments within the educational system.