Psychopathy is a personality disorder that researchers have subdivided into two types: successful and unsuccessful. Nevertheless, little headway has been made regarding how to conceptualize and operationalize success. We consider various accounts of success from the existing literature and make the case for a two-dimensional view of successful psychopathy. Specifically, we contend that successful psychopathy can be conceptualized with two conditions in mind: (a) high social status and (b) lack of serious antisocial behavior. We emphasize that high social status, best described using socioeconomic status (SES), has been largely overlooked in the literature. We tested this idea using a sample of 591 participants who received measures of the triarchic model of psychopathy (i.e., boldness, meanness, and disinhibition), SES, and personality dysfunction. The results demonstrated that, as predicted, the putatively adaptive features of psychopathy (i.e., boldness) were positively related to SES and personality functioning. In contrast, the putatively maladaptive psychopathy features disinhibition and meanness were negatively related to personality functioning, and disinhibition was negatively related to SES. The relevance of boldness to psychopathy and the benefits of conceptualizing success as a continuous variable are discussed.