The current study examined the course of depressive symptoms of young men from early adolescence through young adulthood using a growth model approach and the influence of early parental (i.e., depressive symptoms, antisocial behaviors, substance use) and contextual (i.e., family income and parental marital transitions) risk factors on both the level of depressive symptoms in early adolescence and on changes over a 10-year period, controlling for young men's early antisocial behavior. On average, depressive symptoms of the youths tended to decrease slightly as they reached young adulthood. Among the parental and contextual risk factors, parent's marital transitions was the most significant predictor for the level of depressive symptoms in early adolescence. Parent's marital transitions and family income were also significantly related to changes in depressive symptoms. As hypothesized, there was a significant interaction effect of paternal and maternal depressive symptoms on depressive symptoms in early adolescence and on changes over time. Maternal depressive symptoms were related to the son's depressive symptoms only when the father's depressive symptoms were also high. The results also suggested that parenting practices did not mediate the effects of the parental and contextual risk factors on the development of depressive symptoms among young men.