This research used data from the Longitudinal Study of Australian Children to examine the linkages between parents’ drinking and the drinking of their 14–15 year old children and specifically investigate gender differences and the role of parental monitoring on adolescent drinking. The percentage of parents who drank at levels that exceeded guidelines for reducing both lifetime and single-occasion risk was high. The results showed that risky parental drinking increased the likelihood of adolescent drinking after controlling for a range of socio-demographic risk factors, including drinking among adolescents’ friends. Adolescents with parents who abstained from drinking were less likely to drink. For resident mothers and fathers who were current drinkers, drinking at a risky level was associated with increased rates of adolescent drinking. Rates of adolescent drinking were high in single-parent households, and higher still if the parent regularly exceeded the short-term guidelines, while in two-parent households, rates of adolescent drinking were highest when both parents were risky drinkers. Adolescents who drank alcohol were likely to be more advanced in pubertal status at age 12–13, to be an only child or have older siblings, to have friends who drank alcohol at age 14–15, to have parents born in Australia or an English-speaking country, and to have a grandparent who had an alcohol problem. Risky maternal drinking when adolescents were aged 12–13 increased the likelihood of poorer monitoring of children’s friends and activities two years later, which was subsequently associated with adolescent drinking, but for boys only. Overall, the results suggested that parental drinking (especially if it is frequent and heavy) does increase the likelihood of early adolescent drinking but this association is probably only one part a complex developmental pathway involving parenting practices, family resources, community disadvantage, peer groups and alcohol availability.