Climatic changes are leading to differing patterns and timing of precipitation in grassland ecosystems, with the seasonal timing of precipitation affecting plant biomass and plant composition. No previous studies have examined how drought seasonality affects grasshopper performance and the impact of herbivory on vegetation. We modified seasonal patterns of precipitation and grasshopper density in a manipulative experiment to examine if seasonality of drought combined with herbivory affected plant biomass, nitrogen content, and grasshopper performance. Grass biomass was affected by both precipitation and grasshopper density treatments, while nitrogen content of grass was higher with early-season drought. Proportional survival was negatively affected by initial density, while survival was higher with early drought than with full-season drought. Drought timing affected the outcome, with early summer drought increasing grass nitrogen content and grasshopper survival, while season-long and late-season drought did not. The results support arguments that our knowledge of plant responses to seasonal short-term variation in climate is limited and illustrate the importance of experiments manipulating precipitation phenology. The results confirm that understanding the season of drought is critical for predicting grasshopper population dynamics, as extreme early summer drought may be required to strongly affect Melanoplus sanguinipes (F.) performance.