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The study of reciprocal adaptation in interacting species has been an active and inspiring area of evolutionary research for nearly 60 years. Perhaps owing to its great natural history and potential consequences spanning population divergence to species diversification, coevolution continues to capture the imagination of biologists. Here we trace developments following Ehrlich and Raven’s classic paper, with a particular focus on the modern influence of two studies by Dr. May Berenbaum in the 1980s. This series of classic work presented a compelling example exhibiting the macroevolutionary patterns predicted by Ehrlich and Raven and also formalized a microevolutionary approach to measuring selection, functional traits, and understanding reciprocal adaptation between plants and their herbivores. Following this breakthrough was a wave of research focusing on diversifying macroevolutionary patterns, mechanistic chemical ecology, and natural selection on populations within and across community types. Accordingly, we breakdown coevolutionary theory into specific hypotheses at different scales: reciprocal adaptation between populations within a community, differential coevolution among communities, lineage divergence, and phylogenetic patterns. We highlight progress as well as persistent gaps, especially the link between reciprocal adaptation and diversification.