AbstractBackground A life‐course perspective was used to examine whether a parent's adolescent antisocial behaviour increases the chances of his or her child being involved in antisocial behaviour and, if so, the extent to which different aspects of parenting mediate this relationship.Aim It was hypothesised that there will be significant levels of intergenerational continuity in antisocial behaviour when parents have ongoing contact with the child, and that stress from parenting and ineffective parenting styles will mediate this relationship.Method Longitudinal data from the Rochester Intergenerational Study were used to test these issues in structural equation models for fathers and for mothers.Results Parental antisocial behaviour is significantly related to child antisocial behaviour for mothers and for fathers who have frequent contact with the child, but not for fathers with infrequent contact. For mothers, the impact of adolescent antisocial behaviour on the child's antisocial behaviour is primarily mediated through parenting stress and effective parenting. For high‐contact fathers there are multiple mediating pathways that help explain the impact of their adolescent antisocial behaviour on their child's behaviour.Conclusions The roots of antisocial behaviour extend back at least to the parent's adolescence, and parenting interventions need to consider these long‐term processes. Copyright © 2009 John Wiley & Sons, Ltd.