This paper aims to assess the role of individual types and cumulative life adversity for understanding depressive symptomatology and aggressive behavior. Data were collected in 2011 as part of the Teen Life Online and in Schools Study from 916 ethnically-diverse students from 12 middle, K-8, 6-12 and high schools in the Midwest United States. Youth reported an average of 4.1 non-victimization adversities and chronic stressors in their lifetimes. There was a linear relationship between number of adversities and depression and aggression scores. Youth reporting the highest number of adversities (7 or more) had significantly higher depression and aggression scores than youth reporting any other number of adversities suggesting exposure at this level is a critical tipping point for mental health concerns. Findings underscore an urgent need to support youth as they attempt to negotiate, manage, and cope with adversity in their social worlds.