Puberty is marked by substantial increases and emerging sex differences in psychological disorders and risky behaviors. However, few studies have examined these effects beyond adolescence, and the previous literature has been dominated by samples of White girls. The current study examines the broadest known set of health sequelae related to traditional pubertal markers and peer-relative pubertal timing in a representative sample of 14,545 U.S. youth from the National Longitudinal Study of Adolescent to Adult Health. Maturational timing was assessed by age at menarche for girls and physical development for boys (e.g., facial hair, voice change), and then categorized as early (1 SD below mean), on-time, or late (1 SD above mean) within-sex. Early and late peer-relative timing was assessed by a self-report of looking “much older” or “much younger” than one's peers. We examined psychological (depressive symptoms, antisocial behavior), behavioral (number of sex partners, drug use, physical activity, screen time, sleep hours), and physical health (self-reported health, BMI) outcomes during adolescence and young adulthood in a series of sex-stratified regression analyses using survey weights and a comprehensive set of sociodemographic covariates. Results indicated that, overall, earlier pubertal timing (i.e., maturational timing and peer-relative timing) put both girls and boys at risk during adolescence, while later timing was protective. However, longitudinal models revealed mixed results. For instance, early maturational timing was associated with higher young adult BMI (girls: β = 0.139, p < .01; boys: β = 0.107, p < .01), but later timing for boys was associated with both risky (e.g., more screen time; β = 0.125, p < .05) and health promoting (e.g., more sleep; β = .296, p < .01) behaviors. Analysis of this holistic set of outcomes with sex differences in mind allows for more careful evidence-based recommendations for adolescent health promotion.