Two recent meta-analyses have suggested that boldness, as assessed by the Psychopathic Personality Inventory (PPI) Fearless Dominance dimension, is largely unrelated to total or factor scores on the Psychopathy Checklist—Revised (PCL-R), raising questions concerning the relevance of largely adaptive features to psychopathy. Nevertheless, given that the PCL was developed and validated among prisoners, it may place less emphasis than do other psychopathy measures on adaptive traits, such as fearlessness, social poise, and emotional resilience. We conducted a meta-analysis (N = 10,693) of the relations between (a) boldness, as assessed by the PPI and its derivatives or measures of the triarchic model of psychopathy, and (b) non-PCL-based psychopathy measures across 32 samples. The average weighted correlation between boldness and psychopathy was medium to large (r = .39) and considerably higher than reported in prior meta-analyses; when analyses were restricted to well-validated psychopathy measures, the correlation rose to r = .44. We did not find support for the position that boldness is significantly less related to psychopathy than are the other 2 dimensions of the triarchic model. Our findings strongly suggest that boldness is relevant to at least some well-validated measures of psychopathy, and raise further questions regarding the boundaries of this condition.