This study examined dimensions of callous behaviors in early childhood and the role of these behaviors in the development of conduct problems, as well as responsiveness to a family-centered preventative intervention. Caregiver reports of callous behaviors were examined using exploratory and confirmatory factor analysis. Problem behavior was examined using within- and cross-informant reports of these behaviors. Parenting was measured using observational methods within the context of a randomized control trial of the Family Check-Up with a sample of 731 ethnically diverse boys and girls (followed from ages 2 to 4) at high risk for later conduct problems. Results demonstrated that a measure of deceitful-callous (DC) behaviors had acceptable factor loadings and internal consistency at ages 3 and 4. DC behaviors at age 3 predicted problem behavior concurrently and longitudinally within and across informant. However, DC behaviors did not reduce the effectiveness of the family preventative intervention. These findings have implications for our understanding of behaviors that may precede later callous-unemotional traits and for our understanding of the development and prevention of early starting conduct problems.