While psychopaths (PP) lack anticipatory fear, social phobics (SP) are characterized by excessive fear. Criminal PP, SP and healthy controls (HC) participated in differential aversive delay conditioning with neutral faces as conditioned (CS) and painful pressure as unconditioned stimuli. Functional magnetic resonance imaging revealed differential activation in the limbic-prefrontal circuit (orbitofrontal cortex, insula, anterior cingulate, amygdala) in the HC. By contrast, the PP displayed brief amygdala, but no further brain activation. The SP showed increased activity to the faces in the amygdala and orbitofrontal cortex already during habituation. Thus, a hypoactive frontolimbic circuit may represent the neural correlate of psychopathic behavior, whereas an overactive frontolimbic system may underly social fear.