The relationship between psychopathy and thinking styles that support and maintain a criminal lifestyle is examined using the Psychopathy Checklist: Screening Version (PCL:SV; Hart, Cox, & Hare, 1995) and the Psychological Inventory of Criminal Thinking Styles (PICTS; Walters, 1995). These measures are administered to a sample of 75 patients recruited from a State psychiatric hospital in the northeastern United States. Correlational analyses indicate that the PICTS General Criminal Thinking, Self-Assertion/Deception factor scale, and several criminal thinking style scales are significantly related to psychopathy. The significantly associated criminal thinking scales include Entitlement (r = .44) and Superoptimism (r = .43) with Factors 1 and 2 of the PCL:SV, respectively. Multiple regression analyses reveal that these two criminal thinking scales are the strongest predictors of Factors 1 and 2 of the PCL:SV, respectively. Implications for the cognitive basis of the construct of psychopathy, as well as potential treatment interventions, are discussed. (Published Abstract)