There is limited understanding of parents' role in positive youth/adolescent development through leisure in developing countries. Using a sample of 6626 8th grade students in South Africa, this study examined the interrelationships among parenting practice, adolescents' leisure experience, and substance use. Results of structural equation modeling showed that parental leisure involvement was associated with less substance use, while parental leisure over-control was associated with greater substance use. The relationship of parental leisure involvement to substance use was mediated by healthy leisure engagement. The relationship of parental leisure over-control to substance use, on the other hand, was mediated by leisure boredom and healthy leisure engagement. The model path coefficients had little variation between genders and socioeconomic groups except that parental leisure over-control had a stronger positive relationship with leisure boredom for males than females. Theoretical and practical implications were discussed.