The Personality Assessment Inventory's (PAI's) ability to predict psychopathic personality features, as assessed by the Psychopathy Checklist–Revised (PCL-R), was examined. To investigate whether the PAI Antisocial Features (ANT) Scale and subscales possessed incremental validity beyond other theoretically relevant PAI scales, optimized regression equations were derived in a sample of 281 Canadian federal offenders. ANT, or ANT–Antisocial Behavior (ANT-A), demonstrated unique variance in regression analyses predicting PCL-R total and Factor 2 (Lifestyle Impulsivity and Social Deviance) scores, but only the Dominance (DOM) Scale was retained in models predicting Factor 1 (Interpersonal and Affective Deficits). Attempts to cross-validate the regression equations derived from the first sample on a sample of 85 U.S. sex offenders resulted in considerable validity shrinkage, with the ANT Scale in isolation performing comparably to or better than the statistical models for PCL-R total and Factor 2 scores. Results offer limited evidence of convergent validity between the PAI and the PCL-R.