Many species of territorial songbirds exhibit a behavior known as song-type matching, in which a male sings the same song type that his neighbor is singing. Song-type matching is associated with increased aggression, but researchers have not come to a consensus on its adaptive function. Building on studies that identify singing performance as a variable relevant to sexual selection, we hypothesize that higher-performance singers benefit from matching their opponent's song type because matching improves eavesdroppers' ability to compare the two males' performances. We present a model of song-type choice that predicts that males that can outperform their rivals benefit by matching. In contrast, lower-performance males should avoid both matching and being matched. Our hypothesis is compatible with some existing hypotheses of song-matching function, but it is not compatible with the hypothesis that song matching is a conventional signal of aggression. We offer unique predictions that could be used to test our idea. We speculate that lower-performance individuals might have driven the evolution of repertoire complexity because they stand to benefit from novel, unmatchable songs. The phenomenon that dissimilar signals are less accurately compared than similar signals may favor the evolution of multiple ornaments and of plastic signal development (e.g., song learning) in general.