A distinction between parental behavioral control and psychological control has been elucidated in the literature, yet far less is known about the role of psychological control in youth adjustment broadly or risky behavior in particular. We examined the interrelationship of maternal psychological control, youth psychosocial adjustment, and youth risk behaviors among African American single mother-youth (11–16-year old) dyads (n = 194), families in which youth are more vulnerable to adjustment problems and risky behavior than Caucasian youth or youth from intact homes. Higher levels of maternal psychological control were associated with increased youth psychosocial adjustment problems as well as increased youth risk behavior, after statistically controlling for one domain of behavioral control, parental knowledge about a child’s whereabouts and activities. Furthermore, youth externalizing problems mediated the relation between psychological control and risk behavior. The findings suggest that parenting programs targeting risk behavior among African American youth may benefit from including psychological control among the parenting dimensions that are targeted.