The present study revisited the foundational assumption of empathy deficits in psychopathy by addressing three considerations: (1) a two-componential operationalization of empathy as the congruence between perceiving a target’s emotional state (perceived target emotion) and expressing that emotional state for the target (vicarious emotion); (2) the heterogeneity of empathic emotional expressions; and (3) the multidimensionality of psychopathy. I hypothesized that only fearless dominance/antagonism dimensions would be related to lower scores on empathy components—perceived target emotion and vicarious emotion—only for distress-based emotions (sadness and fear), not for anger. I also hypothesized that all psychopathy dimensions would approach zero relations with empathy indices. First, participants self-reported two-factor, “Triarchic,” and four-factor psychopathy. Next, they read four empathy scenarios each describing a situation in which a target experiences an unfortunate outcome. Each scenario accompanied two distinct resolutions designed to evoke either empathic distress or empathic anger. After reading each resolution, participants rated situational appraisals and empathy components vis-à-vis sadness, fear, and anger. Empathy indices were operationalized by two difference scores: (1) the relative difference between vicarious emotion and perceived target emotion and (2) the absolute correspondence between the two empathy components, such that higher scores represent more empathic responding. Results appeared to be best synthesized by grouping psychopathy dimensions under four classifications: interpersonal antagonism (primary psychopathy, meanness, interpersonal manipulation), risk-taking propensity (boldness, erratic lifestyle), impulsive antisociality (disinhibition, antisocial behavior), and callous affect. Consistent with hypotheses, interpersonal antagonism and callous affect dimensions were generally related to lower scores on empathy components aggregated across resolutions, but inconsistent with hypotheses, were also related to lower scores on empathy difference scores. Somewhat inconsistent with hypotheses, risk-taking propensity dimensions manifested generally weaker patterns on empathy components—including very weakly positive relations to perceived target anger—but similar patterns on empathy difference scores. Somewhat inconsistent with hypotheses, impulsive antisociality dimensions were generally related to lower scores on empathy components but very weakly related to empathy difference scores. All associations remained nearly unchanged after controlling for gender. In summary, the present data are consistent with empathy deficits in psychopathy but also highlight the complexity of this psychopathy-empathy link.