and substance use has received some attention (Hart & Hare, 1989; Smith & Newman, 1990), gender differences have not been thoroughly assessed. The current study examined whether gender modified the relationship between two criminally-relevant constructs, a) psychopathy and its factors and b) drug use. A sample of 318 participants with criminal histories and recent substance use was assessed for psychopathy using the Psychopathy Checklist: Screening Version and for illicit drug use using the Structured Clinical Interview for the Diagnostic and Statistical Manual of Mental Disorders. As expected, the impulsive-antisocial traits (Factor 2) of psychopathy were positively related to a number of drug use characteristics (symptoms, age of drug initiation, extent of drug experimentation), whereas the interpersonal-affective traits (Factor 1) showed a negative relationship with drug abuse symptoms and a positive relationship with age of first use. In terms of gender differences, analyses revealed that women showed a stronger association between Factor 1 traits and later age of initiation compared to men, and that Factor 2, and antisocial facet in particular, were more strongly related to drug abuse in women than men.