Both song and color patterns in birds are thought to evolve rapidly and exhibit high levels of homoplasy, yet few previous studies have compared the evolution of these traits systematically using the same taxa. Here we reconstruct the evolution of song in the New World orioles (Icterus) and compare patterns of vocal evolution to previously reconstructed patterns of change in plumage evolution in this clade. Individual vocal characters exhibit high levels of homoplasy, reflected in a low overall consistency index (CI = 0.27) and retention index (RI = 0.35). Levels of lability in song are comparable to those found for oriole plumage patterns using the same taxa (CI = 0.31, RI = 0.63), but are strikingly dissimilar to the conservative patterns of change seen in the songs of oropendolas (Psarocolius, Ocyalus; CI = 0.82, RI = 0.87), a group closely related to the orioles. Oriole song is also similar to oriole plumage in exhibiting repeated convergence in overall patterns, with some distantly related taxa sounding remarkably similar. Thus, both song and plumage in orioles show repeated convergence in individual elements and in overall patterns across the clade, suggesting that both of these character classes are highly labile between taxa yet highly conserved within the genus. Our results provide new insights into the tempo and mode of evolution in sexually selected traits within and across clades.