The goal of the current study was to determine whether level of psychopathy (measured using the Psychopathic Personality Inventory; PPI) was a predictor of risk-taking (measured using the Balloon Analogue Risk Task-Revised Automatic Version; BART), controlling for demographic variables, substance use, and psychopathology. The sample consisted of 60 male and 30 female inner-city drug-dependent individuals currently enrolled in a residential substance abuse treatment program. Additionally, we examined punishment and reward reactivity (PR and RR, respectively) as well as the Absolute value of punishment reactivity (APR) and reward reactivity (ARR) as measured by the BART as a function of PPI score. Separate regression analyses failed to find a relationship between PPI total score and BART, PR, RR, APR, or ARR. Looking at PPI subscales, results indicated an inverse relationship between the Blame Externalization subscale of the PPI and BART score. Results also indicated that the PPI subscale Machiavellian Egocentricity predicted PR but in the opposite direction than expected. Higher scores on the PPI Carefree Nonplanfulness subscales were found to be related to decreased PR and RR. PPI Coldheartedness subscale predicted higher levels of PR and PPI Blame Externalization subscale predicted lower levels of RR. Lower levels of APR and ARR were found to be related to higher scores on the PPI Blame Externalization subscale. Overall, the results were mixed and did not lend strong support regarding the relationship between risk-taking and psychopathy.