Fearlessness has been described among the traits associated with psychopathy; however, disparities in conceptualizations of fear and how related elements are operationalized among different measures of psychopathic traits have led to some enduring controversy. Here we address a subset of elements characterizing fearlessness represented in thrill-seeking and physical risk-taking among a large sample of incarcerated individuals (n = 688). We examine these relationships utilizing Hare's Psychopathy Checklist Revised (PCL-R), the Psychopathy Personality Inventory-Short Form (PPI-SF), and the Zuckerman Sensation Seeking Scale (SSS). Among males, the Thrill and Adventure Seeking (TAS) scale of the SSS was not related to features of the PCL-R, but was highly correlated with Fearless Dominance (FD) of the PPI-SF. Among females, TAS was only modestly correlated with PCL-R total score, but neither of the two PCL-R factors. PPI-SF FD remained a strong predictor of TAS among females. We argue for a careful consideration of the boundaries of the term "fearlessness" as it relates to diverse manifestations of behavior and varied conceptualizations of psychopathy. We also reiterate apparent differences between males and females in the presentation of psychopathic traits.