Child conduct problems (CP) reflect a heterogeneous collection of oppositional, aggressive, norm-violating, and sometimes violent behaviors, whereas child callous–unemotional (CU) behaviors reflect interpersonal styles of interactions reflecting a lack of guilt and empathy as well as uncaring and shallow emotional responses to others. Taken together, high levels of child CP and CU behaviors are thought to identify a relatively homogenous group of children at elevated risk for persistent and more severe problem behaviors across childhood and into adulthood. Although a large body of research has examined the developmental etiology of CP behaviors, only recently has a developmental psychopathology approach been applied to early CU behaviors. The current study examines multiple levels of contextual influences during the first years of life, including family socioeconomic status, household chaos, and parenting behaviors, on CP and CU behaviors assessed during the first-grade year. Whereas previous studies found associations between parenting behaviors and child problem behaviors moderated by household chaos, the current study found no evidence of moderation. However, path analyses suggest that the associations between child CP and CU behaviors and the contextual variables of socioeconomic status (family income and parental education) and household chaos (disorganization and instability) were mediated by maternal sensitive and harsh–intrusive parenting behavior. Analyses are presented, interpreted, and discussed with respect to both bioecological and family stress models of development.