In a midwestern community sample, we tested for evidence of "hardening" of adolescent cigarette smoking between 1980 and 2001 by comparing adolescent smokers and nonsmokers at these two times on measures indicative of "deviance proneness" in Jessor and Jessor's [Jessor, R., & Jessor, S. L. (1977). "Problem behavior and psychosocial development: A longitudinal study of youth." NY: Academic Press] problem behavior theory. Results produced support for some "hardening" of adolescent smoking, but this was largely confined to younger cohorts. Changing social norms that are reflected in a lowered prevalence of adolescent smoking may have restricted smoking behavior to a somewhat more "deviance prone" segment of the adolescent population. Results illustrate the potential utility of considering changes in the larger social and historical context when studying the development of adolescent risk behavior.