The present study yields an in-depth examination of the interpersonal and affective world of high-security and detention prisoners with possible (Psychopathy Checklist: Screening Version [PCL:SV] ≥ 13) and strong (PCL:SV ≥ 18) indications of psychopathy. A group of male inmates (n = 16) was compared with noncriminal and non–personality disordered controls (n = 35) on measures of self and other (Young Schema Questionnaire–Short Form [YSQ-SF], Inventory of Interpersonal Problems–Circumplex Scales [IIP-C]), and the experience and regulation of affect (Positive and Negative Affect Schedule [PANAS], Emotion Control Questionnaire 2 [ECQ2]). Results confirm the established grandiose, dominant, and callous characteristics of the psychopath (PCL:SV, Structured Clinical Interview for DSM-IV Axis II Disorders [SCID-II], DSM-IV and ICD-10 Personality Questionnaire [DIP-Q], IIP-C), while demonstrating personal distress and important nuances and variations in psychopathic offenders’ interpersonal and affective functioning (YSQ-SF, PANAS, ECQ2, SCID-II, DIP-Q). These preliminary findings support, expand, and challenge the ordinary portrayal of the psychopath and, if replicated in larger samples, point to a need for an expansion or reformulation of the concept, measurement, and treatment of psychopathy.