Callous unemotional traits (CU traits) are a risk factor for youth misconduct, yet, questions remain regarding their etiology, as well as other dimensions of psychopathy, namely impulsivity/sensation-seeking (INS) and grandiosity/deceitfulness (GD). Fearless temperament and problematic parenting have each been proposed as risk factors for CU traits, but few studies have investigated their simultaneous influence, particularly in middle childhood or by considering specific aspects of parenting. The current study thus aimed to investigate in a community sample of young children (N = 50, 56% female, ages 6-9) how fearlessness and particular parenting factors uniquely, and in combination, concurrently predict CU, INS, and GD traits. Given the small sample, effect sizes were considered in addition to significance tests. Fearlessness and parenting dimensions tended to show small- to medium-sized correlations with CU, INS, and GD. Regression analyses revealed unique associations between inconsistent discipline and both GD (β =.103, p= .003) and INS (β =.073, p= .037), and between fearlessness and INS (β =.108, p=.001). A unique interaction was also found between fearlessness and monitoring on CU (β = -.090, p=.014). Post-hoc probing revealed that at above-average levels of monitoring, fearlessness was positively related to CU traits (β=.07, p=.02). However, at relatively low monitoring, there was an inverse relationship between CU traits and fearlessness (β=-.09, p=.04). Findings suggest that child fearlessness and specific parenting behaviors may play important roles in predicting risk for specific psychopathic traits. However, study limitations constrained inferences that could be drawn. If replicated, these findings may help inform early intervention efforts for youth at risk for psychopathy.