Neuroimaging has suggested that amygdala reactivity to emotional facial expressions is associated with antisocial behavior (AB), particularly among those high on callous–unemotional (CU) traits. To investigate this association and potential moderators of this relationship, including task/stimuli effects, subregional anatomy of the amygdala, and participant race, we used fMRI in a sample of 167 racially diverse 20-year-old men from low-income families. We found that AB, but not CU traits, was negatively related to amygdala reactivity to fearful faces. This result was specific to fearful faces and strongest in the centromedial subregion of the amygdala. Arrest record was positively related to basolateral amygdala reactivity to fearful and angry faces. Results were strongest among those identified as African American and not present in those identified as European American. Our findings suggest substantial complexity in the relationship between amygdala function and AB reflecting moderating effects of task stimulus, subregional anatomy, and race.