Recent advances in the operationalization of psychopathy have led to an increased understanding of the boundaries, the structure, and the nomological network of its construct. Research has reached a point where the empirical identification of replicable and theoretically meaningful psychopathy variants may lead to further advances in the field. We reviewed for theoretical models that account for psychopathy subtypes and conducted a classification study of 91 incarcerated men who met conventional criteria for high levels of psychopathy as defined by Hare’s (1991) Psychopathy Checklist – Revised. We expanded upon the methodology of previous research on psychopathy subtypes by utilizing a comprehensive personality assessment instrument (the Shedler-Westen Assessment Procedure – II; Westen & Shedler, 1999) and a prototype matching approach to classification. The analyses revealed a primary (malignant narcissistic) subtype and a secondary (hostile and dysregulated) subtype that were generally consistent with the previous literature and lent support to Patrick’s (2007) application of the dual-process model and the neurophysiological theory of affect to psychopathy. We also found limited evidence for a pseudopsychopathic (thrill-seeking) subtype. External validation analyses, statistical controls, and incremental validity analyses provided substantial support for the primary and secondary subtypes (but not for the thrill-seeking one). Future studies on the diagnosis, etiology, prevention, and treatment of psychopathy will likely benefit from taking into account its primary and secondary variants.