This study aimed at assessing developmental trajectories of risk behaviors from adolescence into young adulthood and their associations with outcomes in young adulthood (i.e. education, employment). Data of the TRacking Adolescents' Individual Lives Survey (TRAILS) including 2,149 participants (mean age = 13.6, SD = 0.5, 51% girls) were used to examine the development of alcohol, cannabis, smoking, and externalizing behavior. The results showed that the associations between these risk behaviors varied with age, and revealed varying developmental patterns throughout adolescence. Most notably alcohol use did not covary strongly with the other risk behaviors. The often assumed peak in risk behavior in adolescence was only found in a small group, and only for alcohol (7.4%) and cannabis use (3.4%), but not for smoking or externalizing behavior. Most adolescents revealed only low involvement in risk behavior, with the largest differences between low and high trajectories emerging in late adolescence (> 19 years). Clustering of risk behavior throughout adolescence is rather the exception than the rule and depends on age and type of risk behavior. Differences in risk behavior between individuals become the largest in late adolescence, possibly influencing successful transition into adulthood visible in educational attainment and employment.