Two studies examined the consistency of associations between specific components of psychopathy and two indices of drug use: (a) abstinence and (b) severity (i.e., counts) of lifetime substance use disorder (SUD) symptoms. Participants were 418 male county jail inmates in Illinois (Study One) and 354 male state prison inmates in New Mexico (Study Two). Across samples, lifestyle and antisocial trait ratings were associated with a reduced likelihood of abstinence from most substances. Lifestyle traits were also uniquely associated with severity of substance dependence ratings. Consistent with prior research, interpersonal traits were uniquely related to cocaine indices in both samples. Furthermore, analyses revealed negative associations between the affective features of psychopathy and alcohol dependence in one sample (Study Two), and illicit substance use across samples. These findings demonstrate the robustness of the associations between the interpersonal and affective features of psychopathy and specific aspects of substance (mis)use.