The study examined the relationship between psychopathy and anxiety in 147 community boys. Children and their guardians completed self- and parent-report measures of child psychopathy (APSD) and child anxiety (MASC). In the literature, the psychopathy and anxiety association has been conceptualized as nonexistent, more a function of fearlessness, and a consequence of the impulsive lifestyle of psychopathy. The study suggested that anxiety may also be a reaction to fluctuating affective and interpersonal features that may diminish with age. Structural equation modeling was used to examine these hypotheses. The inverse relationship theory and the lifestyle consequence theory were not supported in the young (ages 8-14) community sample. However, the expected association with fearfulness and psychopathy was present, although it was limited to the impulsive lifestyle features. As posited, higher levels of self-report anxiety were associated with higher levels of psychopathy, including callous-emotional features. Age was not shown to be a significant moderator of the relationship. Regardless, there was a clear developmental distinction that conflicted with previous theory as well as the adult psychopathy literature. The current results suggest that anxiety may have important implications for the development and treatment of psychopathy in children.