Theories and prior research have outlined a constellation of adolescent risk behaviors that tend to co-occur, reflecting a general pattern. Although their generality has largely been supported, there is some question about how to best study and portray the relationship among these behaviors. This study used data from a survey administered to high school youth (n = 2549, 38 schools). The general population sample comprised an even split between boys and girls, averaged roughly 16 years of age, and was 59% White and 10% Hispanic/Latino. Using latent class analysis, four subgroups, comprised of varying types and degrees of risky behavior, were identified. Specifically, there were two groups that "abstained" and "experimented" with risky behaviors and two others that had higher, but somewhat distinct, patterns of such activities. These groups were then examined in relation to youth characteristics (e.g., mental and physical health, school performance) and socio-environmental factors (e.g., social support, parental monitoring) that may be useful for better understanding "problem behavior syndrome" and development of prevention strategy.