Background: The linkage between sleep quality and weight status among teenagers has gained more attention in the recent literature and health policy but no consensus has been reached. Methods: Using both a propensity score method and multivariate linear regression for a cross-sectional sample of 2,113 teenagers, we analyzed their body mass index (BMI) in relation to sleep quality while controlling for family characteristics (household income, parent/guardian level of education, disability status, work night shift, and smoking) and individual factors (age, sex, regular exercise, smoking, employment, and feeling secure in the neighborhood). Sleep quality was assessed using 3 scales: difficulty in initiating sleep, difficulty in maintaining sleep, and non-restorative sleep, based on Diagnostic and Statistical Manual of Mental Disorders-IV-defined insomnia. Results: Considering all 3 types of poor sleep quality, 20.9% of teenagers in Taiwan experienced some form of sleep problems. After adjusting for the other variables, 2 factors independently and statistically predicted sleep problems: current smoking and working night shifts by the head of the household. Teens experiencing difficulty in initiating sleep had higher BMIs ranging from 0.86 to 1.41 units. Conclusions: Efforts to address childhood obesity need to take into consideration sleep problems that are highly prevalent among teenagers. (Contains 3 tables.)