We conduct a case study of observed and simulated maximum daily 8-h average (MDA8) ozone (O3) in three US cities for summers during 1996–2005. The purpose of this study is to evaluate the ability of a high resolution atmospheric chemistry model to reproduce observed relationships between meteorology and high or extreme O3. We employ regional coupled chemistry-transport model simulations to make three types of comparisons between simulated and observational data, comparing (1) tails of the O3 response variable, (2) distributions of meteorological predictor variables, and (3) sensitivities of high and extreme O3 to meteorological predictors. This last comparison is made using two methods: quantile regression, for the 0.95 quantile of O3, and tail dependence optimization, which is used to investigate even higher O3 extremes. Across all three locations, we find substantial differences between simulations and observational data in both meteorology and meteorological sensitivities of high and extreme O3.