Current evidence is equivocal as to whether adolescent's perception of weight status is linked to both healthy and risky behaviors. This study examined the association between accurate and inaccurate perception of weight and self-reported health and risk behaviors among a diverse sample of obese, urban adolescents. Data were analyzed from 1,180 participants in the 2009 Philadelphia Youth Risk Behavior Survey. Health behaviors of obese students self-identifying as very or slightly overweight were compared to obese students who underestimated their weight status. Accurate self-identifiers of weight status were significantly more likely to report trying to lose weight, bullying victimization, and suicide attempts as compared to obese students underestimating their weight status. Findings suggest that it is important for school nurses to understand that perceived weight status confers distinct risk profiles and differing needs for health-related services related to the physical, mental, and social health of adolescents. (Contains 2 tables.)