This study used an experimental, longitudinal field trial involving random assignment to the Family Check-Up (FCU) to explore the social ecology of adolescent antisocial behavior. A sample of 998 youths and their families was followed from early to late adolescence (age 12 to 18-19). In the intervention condition, 115 families (23%) elected to receive the FCU. In general, random assignment to the FCU in middle school was associated with reductions in late adolescence antisocial behavior (age 18-19). Variable-centered analyses revealed that the effects were mediated by reductions in family conflict from early to middle adolescence (age 12-15). The link between family conflict and antisocial behavior in turn was mediated by association with deviant peers at age 17; parental monitoring at age 17 was also influential but did not attain the status of a mediator. Person-oriented analyses suggested that the FCU was associated with declining trajectories of family conflict and rising trajectories of parental monitoring but was not associated with trajectories of deviant peer association. A dual-trajectory analysis indicated that the pathways to adolescent antisocial behavior were myriad and varied, suggesting new directions for developmental and intervention research.