OBJECTIVE This study aimed to study conditions associated with depressive symptoms at ages 8 and 18 in a representative birth cohort of Finnish males. METHODS The participants in this community-based 10-year follow-up study consisted of 2,348 boys born in 1981. At age 8, three informant sources were used: parents, teachers, and the children themselves. Depressive symptoms were established using the Children's Depression Inventory (CDI). At age 18, self-report questionnaires were used to study the boys' family factors, life events, adaptive functioning, and substance use. Depressive symptoms at age 18 were established using Beck's Depression Inventory (BDI). RESULTS Poor adaptive functioning at age 18 was independently associated with both child and late adolescent depressive symptoms. Use of illicit drugs and somatic health problems were independently associated with later depressive symptoms. Parental divorce in early childhood independently predicted depressive symptoms both in childhood and in late adolescence. Teacher reports of child's total problems at age 8 independently predicted depressive symptoms at age 18. CONCLUSIONS Depression in males at ages 8 and 18 is particularly associated with stressful life events in childhood, whereas late depression is associated with somatic health problems and substance use. Further population-based studies comparing conditions associated with childhood and adolescent depression are needed.