Facial expressions play a critical role in social interactions by eliciting rapid responses in the observer. Failure to perceive and experience a normal range and depth of emotion seriously impact interpersonal communication and relationships. As has been demonstrated across a number of domains, abnormal emotion processing in individuals with psychopathy plays a key role in their lack of empathy. However, the neuroimaging literature is unclear as to whether deficits are specific to particular emotions such as fear and perhaps sadness. Moreover, findings are inconsistent across studies. In the current experiment, 80 incarcerated adult males scoring high, medium, and low on the Hare Psychopathy Checklist-Revised (PCL-R) underwent functional magnetic resonance imaging (fMRI) scanning while viewing dynamic facial expressions of fear, sadness, happiness, and pain. Participants who scored high on the PCL-R showed a reduction in neuro-hemodynamic response to all four categories of facial expressions in the face processing network (inferior occipital gyrus, fusiform gyrus, and superior temporal sulcus (STS)) as well as the extended network (inferior frontal gyrus and orbitofrontal cortex (OFC)), which supports a pervasive deficit across emotion domains. Unexpectedly, the response in dorsal insula to fear, sadness, and pain was greater in psychopaths than non-psychopaths. Importantly, the orbitofrontal cortex and ventromedial prefrontal cortex (vmPFC), regions critically implicated in affective and motivated behaviors, were significantly less active in individuals with psychopathy during the perception of all four emotional expressions.