The present research sought to examine the interrelations of emotion, crime characteristics, and self-reported psychopathy; and to examine criterion related validity of the Self-Report Psychopathy Scale Short-Form (SRP-SF). One hundred Canadian adult male offenders were interviewed with a series of structured questionnaires examining offense-related distress, shame, and guilt; offense instrumentality-reactivity; psychopathy; and institutional violence. Results revealed a significant negative association between SRP-measured psychopathy and offense-related guilt, but not offense-related shame or distress. Higher psychopathy scores were also associated with greater planning and control of the offense, higher levels of anger during the offense, and engagement in institutional violence. Receiver Operator Characteristic (ROC) analyses demonstrated SRP total, affective, and lifestyle facet scores yielded the strongest predictive accuracy for institutional violence followed by the interpersonal and antisocial facets. Results provide support for the predictive accuracy and construct validity of SRP-SF. Findings also reflect the instrumental-reactivity continuum of offenses with potential implications for the treatment and correctional needs of high psychopathy men, both in terms of emotional and interpersonal areas, in addition to the more traditionally targeted criminogenic foci. Researchers and clinician alike are encouraged to further explore this understudied topic.