Recent adaptive radiations provide striking examples of convergence [1-4], but the predictability of evolution over much deeper timescales is controversial, with a scarcity of ancient clades exhibiting repetitive patterns of phenotypic evolution [5, 6]. Army ants are ecologically dominant arthropod predators of the world's tropics, with large nomadic colonies housing diverse communities of socially parasitic myrmecophiles [7]. Remarkable among these are many species of rove beetle (Staphylinidae) that exhibit ant-mimicking "myrmecoid" body forms and are behaviorally accepted into their aggressive hosts' societies: emigrating with colonies and inhabiting temporary nest bivouacs, grooming and feeding with workers, but also consuming the brood [8-11]. Here, we demonstrate that myrmecoid rove beetles are strongly polyphyletic, with this adaptive morphological and behavioral syndrome having evolved at least 12 times during the evolution of a single staphylinid subfamily, Aleocharinae. Each independent myrmecoid clade is restricted to one zoogeographic region and highly host specific on a single army ant genus. Dating estimates reveal that myrmecoid clades are separated by substantial phylogenetic distances-as much as 105 million years. All such groups arose in parallel during the Cenozoic, when army ants diversified into modern genera [12] and rose to ecological dominance [13, 14]. This work uncovers a rare example of an ancient system of complex morphological and behavioral convergence, with replicate beetle lineages following a predictable phenotypic trajectory during their parasitic adaptation to host colonies.