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Given the high rates of aggressive behavior among highly psychopathic individuals, much research has sought to clarify the nature of the relation between psychopathy and aggression. The present study examined relations between Fearless Dominance (PPI FD), Self-Centered Impulsivity (PPI SCI), and Coldheartedness (PPI CH) Factors of the Psychopathic Personality Inventory (PPI; Lilienfeld & Andrews, 1996) and aggression dimensions (premeditated and impulsive aggression) in a sample of substance users receiving inpatient treatment. At the univariate level, PPI FD traits were significantly and positively related to premeditated aggression, but were not significantly related to impulsive aggression. PPI SCI traits were positively related to both forms of aggression, whereas PPI CH was not significantly related to either aggression dimension. Emotion regulation difficulties, as measured by the Difficulties with Emotion Regulation Scale (DERS; Gratz & Roemer, 2004), were negatively related to PPI FD traits, positively related to PPI SCI traits, and negatively related to PPI CH traits. Both PPI SCI and PPI FD traits exerted significant indirect effects on impulsive aggression through the DERS. In contrast, the DERS did not mediate the relations between psychopathic traits and premeditated aggression. Results provide a more nuanced understanding of the psychopathy–aggression relations and suggest that difficulties with emotion regulation may be an important mediator of the relations between psychopathy factors and impulsive aggression.