The aim of the present study was to make a 16-year follow-up of children of psychosocial risk mothers as concerns emotional/behavioural problems, self-esteem, life events, and academic grades. Forty-three teenagers (index group) and 61 reference teenagers were personally interviewed and asked to answer the Youth Self-report (YSR), the Self-image questionnaire I Think I Am, and a Life Event questionnaire. Their final grades from the 9-year compulsory school were studied. The results showed that boys, especially the sons from families with alcohol/drug problems, displayed poorer mental health, a more negative self-image, had experienced more negative life events, and had to a greater extent not successfully completed the 9-year compulsory school. More teenagers in the index group had been placed in foster care, had a less positive outlook about their future, were more often smokers, and more of them (girls) had seriously considered committing suicide than the teenagers in the reference group. It was concluded that boys of psychosocial risk mothers are less well off than teenagers of non-risk mothers at the age of 16 as concerns psychosocial well being. It is of great importance to devote attention to these children at an early stage of life in order to be able to provide them with the support that may prevent development of future problems.