BackgroundCallous-unemotional behaviors identify children at risk for severe and chronic antisocial behavior. Research is needed to establish pathways from temperament and parenting factors that give rise to callous-unemotional behaviors, including interactions of positive versus harsh parenting with child fearlessness. MethodsMultimethod data, including parent reports and observations of parent and child behavior, were drawn from a prospective, longitudinal sample of low-income boys (N=310) with assessments at 18, 24, and 42months, and at ages 10-12years old. ResultsParent-reported callous-unemotional, oppositional, and attention-deficit factors were separable at 42months. Callous-unemotional behaviors at 42months predicted callous-unemotional behaviors at ages 10-12, accounting for earlier oppositional and attention-deficit behaviors and self-reported child delinquency at ages 10-12. Observations of fearlessness at 24months predicted callous-unemotional behaviors at 42months, but only when parents exhibited low observed levels of positive parenting. The interaction of fearlessness and low positive parenting indirectly predicted callous-unemotional behaviors at 10-12 via callous-unemotional behaviors at 42months. ConclusionsEarly fearlessness interacts with low positive parenting to predict early callous-unemotional behaviors, with lasting effects of this person-by-context interaction on callous-unemotional behaviors into late childhood.