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Abstract Learned traits, such as foraging strategies and communication signals, can change over time via cultural evolution. Using historical recordings, we investigate the cultural evolution of birdsong over nearly a 50-year period. Specifically, we examine the parts of white-crowned sparrow (Zonotrichia leucophrys nuttalli) songs used for mate attraction and territorial defense. We compared historical (early 1970s) recordings with contemporary (mid-2010s) recordings from populations within and near San Francisco, CA and assessed the vocal performance of these songs. Because birds exposed to anthropogenic noise tend to sing at higher minimum frequencies with narrower frequency bandwidths, potentially reducing one measure of song performance, we hypothesized that other song features, such as syllable complexity, might be exaggerated, as an alternative means to display performance capabilities. We found that vocal performance increased between historical and contemporary songs, with a larger effect size for urban songs, and that syllable complexity, measured as the number of frequency modulations per syllable, was historically low for urban males but increased significantly in urban songs. We interpret these results as evidence for males increasing song complexity and trilled performance over time in urban habitats, despite performance constraints from urban noise, and suggest a new line of inquiry into how environments alter vocal performance over time.