The study investigated if proximal contextual risk (number of adverse life events experienced in the last year) or distal contextual risk (number of adverse life events experienced before the last year) is a better predictor of adolescent psychopathology and prosocial behavior. It also tested for the specificity, accumulation and gradient of contextual risk in psychopathology and prosocial behavior, and for the interaction between proximal and distal contextual risk in psychopathology and prosocial behavior. The sample was 199 11-18 year old children from a socio-economically disadvantaged area in North-East London. The Strengths and Difficulties Questionnaire (SDQ), which measures four difficulties (hyperactivity, emotional symptoms, conduct problems, and peer problems) and prosocial behavior, was used. Confounders were age, gender, and maternal educational qualifications. To model the relationship between the five SDQ scales and contextual risk multivariate response regression models and multivariate response logistic regression models that allow the error terms of the scale specific models to be correlated were fitted. This study highlighted the importance of proximal contextual risk in predicting both broad and externalizing psychopathology, and the importance of considering risk accumulation rather than specificity in predicting psychopathology. By showing that the number of proximal adverse life events experienced had a steady, additive effect on broad and externalizing psychopathology, it also highlighted the need to protect adolescents experiencing current risk from further risk exposure. By showing that the number of distal adverse life events experienced did not affect the proximal risk’s impact on either broad or externalizing psychopathology, it highlighted the need to protect all adolescents, irrespective of experience of early life adversities, from risk.