This study used model-based cluster analysis to identify subtypes of men who scored high in overall psychopathy (i.e., ≥ 95th percentile on the Triarchic Psychopathy Measure; n = 193) from a larger sample evaluated for service in the Finnish military (N = 4043). Cluster variates consisted of scores on distinct facets of psychopathy together with a measure of negative affectivity. The best-fitting model specified 2 clusters, representing “primary” (n = 110) and “secondary” psychopathy (n = 83) groups. Compared to a low-psychopathy comparison group (n = 1878), both psychopathy subgroups showed markedly elevated levels of externalizing symptoms and criminal behavior. Secondary psychopathic participants also reported high levels of internalizing problems including anxiousness, depression, and somatization, and scored higher on the disinhibition facet of psychopathy relative to the primary group. By contrast, primary psychopathic individuals reported fewer internalizing problems than either the secondary psychopathy or comparison groups and scored higher on the boldness facet of psychopathy. Primary psychopathic participants also had higher rates of violent crimes than the secondary psychopaths. Implications for conceptualizing and studying psychopathy in nonforensic populations are discussed.