U.S. trends in population health suggest alarming disparities among young adults, who are less healthy across most measureable domains than their counterparts in other high-income countries; these international comparisons are particularly troubling for women. To deepen our understanding of gender disparities in health and underlying behavioral contributions, we document gender-specific clusters of health behavior among U.S. young adults using nationally representative data from the National Longitudinal Study of Adolescent to Adult Health. We find high levels of poor health behavior, but especially among men; 40 percent of men clustered into a group characterized by unhealthy behavior (e.g., poor diet, no exercise, substance use), compared to only 22 percent of women. Additionally, women tend to age out of unhealthy behaviors in young adulthood more than men. Further, we uncover gender differences in the extent to which sociodemographic position and adolescent contexts inform health behavior clustering. For example, college education was more protective for men, whereas marital status was equally protective across gender. Parental drinking mattered for health behavior clustering among men, whereas peer drinking mattered for clustering among women. We discuss these results in the context of declining female advantage in U.S. health and changing young adult social and health contexts.