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To investigate the relationship between body mass and health-related quality of life (HRQOL) among Singaporean adolescents. Variation in this relationship by age, gender and ethnicity, and association of HRQOL with change in body mass over time and with demographic, socioeconomic and health variables were also assessed. HRQOL was assessed for Singaporean adolescents aged 11–18 from their own ( N = 1,249) and their parent’s ( N = 948) perspective using PedsQL™ 4.0 generic core scales. Body mass, measured as body mass index z-score based on the WHO Reference 2007, was categorized as thin, healthy weight, overweight and obese. Multiple linear regression models assessed the relationship between current body mass and HRQOL, adjusting for demographic, socioeconomic and health variables. Differences between adolescent and parent-proxy reported HRQOL were also investigated. Obese adolescents (and their parents) reported significantly lower HRQOL, overall and in most domains, compared to healthy weight adolescents. Parents tended to report lower HRQOL for their adolescents than the adolescents did themselves; however, this difference was much larger and statistically significant for obese adolescents. Obesity is associated with reduced HRQOL among adolescents. The effect in these Singaporean adolescents is similar to that in populations with higher rates of obesity. Awareness of this relationship can make it easier for health professionals, teachers, parents and peers to be supportive of obese adolescents. [ABSTRACT FROM AUTHOR]