The economics literature supports a link between labor market measures, such as earnings, and health conditions, such as obesity. There is reason to believe the effects of obesity on wages may vary for high- and low-earning individuals and that obesity wage effects may evolve over a lifecycle or from generation to generation. Drawing on data from two longitudinal surveys, we estimate quantile and fixed effect quantile regressions, among others, to further examine the obesity wage effect. Results suggest an increasingly severe penalty across the wage distribution for females. Specifically, the highest-earning women may be penalized as much as five times that of the lowest earners. Results for males suggest that penalties may be present at select wage levels, while prior research has generally found no male obesity penalty. We also provide evidence that the obesity penalty has increased across generations and limited evidence that it may slow earnings growth over one’s lifetime.