Methodological and conceptual differences across studies have impeded our understanding of the relationship between psychopathy and internalizing psychopathology. To shed further light on this question, we undertook correlational and structural-modeling analyses of data from two samples to characterize how facets of psychopathy relate to internalizing psychopathology when assessed using multidimensional measures of each construct (i.e., Triarchic Psychopathy Measure, Inventory of Depression and Anxiety Symptoms). Participants for Study 1 were 470 undergraduates and community-dwelling adults who completed these measures in self-report form; participants for Study 2 were 301 community-dwelling adults who completed informant-rating versions of these measures (as applied to a known-other). Across samples, analyses revealed sharply contrasting associations for the three triarchic-model facets with internalizing psychopathology and its subdomains, with boldness relating negatively in most cases, disinhibition relating positively in most cases, and meanness exhibiting mostly null associations. Results provide a nuanced picture of associations between psychopathic symptomatology and internalizing problems.