Theories of plant defense expression are typically based on the concepts of tradeoffs among traits and of phylogenetic conservatism within clades. Here, I review recent developments in phylogenetic approaches to understanding the evolution of plant defense strategies and plant–herbivore coevolutionary interactions. I focus particularly on multivariate defense against insect herbivores, which is the simultaneous deployment of multiple traits, often arranged as convergently evolved defense syndromes. Answering many of the outstanding questions in the biology of plant defense will require generating broad hypotheses that can be explicitly tested by using comparative approaches and interpreting phylogenetic patterns. The comparative approach has wide-spread potential to reinvigorate tests of classic hypotheses about the evolution of interspecific interactions.