We examined historical change in the association between adolescent deviance proneness and marijuana use using 26 years (from 1979 through 2004) of national 12th grade data from the Monitoring the Future (MTF) study. “Deviance proneness” was measured using a latent factor model of behavioral and personality characteristics that underlie both substance use and antisocial disorders. Marijuana use was measured both in terms of annual frequency of use and degree of involvement with marijuana. Separate within-gender structural equation models were used to determine whether links between deviance proneness and marijuana use were consistently significant and invariant in magnitude across 13 two-year historical cohorts. Overall results affirmed the established association between adolescent deviance proneness and both the frequency of marijuana use as well as regular use. Among male youth, the size of the association between deviance proneness and marijuana use was significantly smaller at the cohort of lowest population prevalence (1991/92) compared to cohorts marking peaks in marijuana use prevalence, thus suggesting a “softening” historical trend. By contrast, the prediction of female marijuana use from deviance proneness was not consistently related to historical shifts in population prevalence of marijuana use. Study findings point to the utility of risk-focused prevention programming that targets early precursors of both antisocial and substance use disorders.