The dialectic between the adolescent quest for autonomy and parents’ desire to regulate this quest are explored by examining the extent to which the association between adolescent work intensity and substance use is mediated and moderated by parenting practices. Results using data from the National Survey of Youth and Religion (N = 3,290) show that the association between work intensity and alcohol use is mediated by parenting practices. There is also limited support for the moderational role of parental monitoring with respect to heavy drinking. Finally, connections among work intensity, parenting practices, and substance use are pronounced for adolescents younger than 16 years of age. These findings suggest the importance of a multifaceted view of parenting practices that both shape and are shaped by their adolescent’s search for independence.