Many birds have colorful plumage ornaments that utilize carotenoid pigments, and these are often displayed in signaling contexts. Researchers in behavioral ecology have focused on examining carotenoids in general, and red carotenoids in particular, because they may be an honest index of individual condition or quality. However, few studies have examined the evolutionary changes in carotenoid-based coloration across a phylogeny. We used reflectance spectrometry to examine carotenoid-based coloration across the New World blackbirds (Icteridae). We scored discrete character states based on these measurements and mapped them onto the icterid phylogeny. Our results indicate that red coloration has been gained six times in the blackbirds from a common ancestor that exhibited yellow ornamentation. This result was supported by both parsimony and likelihood methods of ancestral state reconstruction and by each of three different scoring methods. Thus, multiple lineages of icterids have convergently evolved red patches from a common ancestor that most likely used yellow. Several other studies have observed repeated gains of red coloration, which suggests that our observations may reflect a directional trend common among avian clades.