Abstract The comorbidity of drug abuse and various forms of psychopathology is pervasive and well documented. In particular, the incidence of depression, anxiety, and antisocial personality disorder is high among substance abusers relative to non-drug abusers. Offender populations have a high rate of substance abuse, and some studies suggest that the incidence of psychopathology may be even greater than in order drug using groups. In order to identify specific types of psychopathology as they relate to drug preferences and frequency of use among drug-using offenders, arrestees at the Baltimore City Detention Center were examined. During extensive interviews, drug-abusing arrestees provided information pertaining to their backgrounds, childhood histories, biological relatives, present behaviors, and criminal and drug histories. Additionally, several psychological inventories were administered to evaluate the presence of depression, anxiety, psychopathy, and impulsivity. Results indicate that the frequency with which subjects reported using specific drugs and drug of choice were significantly associated with particular measures of psychopathology. A composite measure of psychopathy was especially related to the frequency of alcohol, marijuana, and cocaine use. Subjects who reported using cocaine on a frequent basis scored high on measures of hostility and reported committing more property crimes, while violent crimes were more likely to be reported by subjects scoring high on the measure of psychopathy. Other noteworthy findings will be discussed along with the limitations of this study.