The current study utilized a longitudinal design to explore the effect of early child impulsivity and rejecting parenting on the development of problematic behaviors in adolescence and early adulthood. Using a low-income sample of 310 mothers and their sons, we examined the direct and interactive effects of child impulsivity and rejecting parenting at age 2 on aggression and substance use at ages 12, 15, and 22, as well as risky sexual behavior at ages 15 and 22. Results revealed that rejecting parenting at age 2 predicted greater aggression at age 12 and risky sexual behavior at ages 15 and 22. Early impulsivity had few direct effects on later outcomes, with the exception of greater substance use at age 22. Instead, impulsivity emerged as a significant moderator in the link between rejecting parenting and aggression at all three ages and substance use at age 15. Specifically, early rejecting parenting predicted greater aggression and substance use only for children high in impulsivity. Findings highlight the potential for early child and parenting risk factors to have long-term implications for adjustment, with the combination of high impulsivity and rejecting parenting being particularly deleterious for problems of aggression throughout adolescence and into early adulthood.