Using a sample of 3,977 youths from the National Longitudinal Survey of Youth (NLSY97), this study examines the unique characteristics of single-custodial-father families with adolescents and the effects of single fathers' involvement and parenting on outcomes in emerging adulthood. Findings suggest that single-custodial-father families are distinct from single-mother and 2-biological-parent families in terms of sociodemographic characteristics, parenting styles, and involvement. Parenting styles and involvement mediate the differences between single-father families and 2-parent families in terms of high school completion and disconnectedness and partially mediate differences for single-custodial-father families with a partner. Family and sociodemographic characteristics are also associated with being disconnected for adolescents residing with a cohabiting custodial father.