The purpose of this study was to understand the relationship between self-esteem and the Face Stimulus Assessment (FSA) by analyzing the difference in characteristics of the FSA results in response to the level of adolescents’ self-esteem. The assessments were administered to 229 second- and third-grade middle school students in city U. A cross-tabulation test and discriminant analysis were conducted to estimate the characteristics of FSA responses by the degree of self-esteem. The results were as follows. In FSA stimulus drawing Ⅰ, the statistically significant variables by the degree of self-esteem were “Prominence of Color,” “Color Fit,” “Implied Energy,” “Logic,” “Details of Object,” “Line Quality,” “Repetitiveness,” and “Space,” and the discriminant power of the variables was 77.7%. In FSA stimulus drawing Ⅱ, “Prominence of Color,” “Color Fit,” “Implied Energy,” “Realism,” “Development Level,” “Line Quality,” “Repetitiveness,” “Emotional Contents,” and “Space” were statistically significant, having 71.9% of the discriminant power. The findings show that the FSA can be used as a predictive tool to complement the limit of self-reported questionnaires to screen the extent of adolescents’ self-esteem.