Given the challenges associated with psychopathic and personality disordered offenders, further insight is needed. One way of doing this is by looking at offending from the first-person perspective. The study investigated the criminal narrative experience (CNE) of this population during the commissioning of crimes. Twenty-two high-risk male offenders were recruited and a questionnaire design was used. The data were analysed using Smallest Space Analysis which revealed four themes consistent with Ioannou, Canter, and Youngs’s CNE framework: depressed victim, distressed revenger, calm professional, and elated hero. Independent samples t tests explored whether personality disorders related to CNE themes, and Pearson’s product–moment correlation was used to explore the relationship between psychopathy and the CNE themes. Borderline personality disorder identified with the depressed victim. Paranoid and schizoid personality disorders did not identify with the calm professional. There was no significant relationship between psychopathy and the CNE themes. The theoretical and practical implications are discussed.