Urbanization results in novel ecosystems with unique challenges. These may lead to problems during song learning or development and could result in the singing of atypical songs. During studies of Mountain Chickadees (Poecile gambeli) and urbanization in British Columbia, Canada, we observed males singing atypical songs along an urbanization gradient. We found that eight of 78 males consistently sang atypical songs and the odds of singing atypical songs increased with urbanization. We explored several explanations including habitat quality, population density, and bioacoustics. Future studies investigating causes and consequences of atypical singing will clarify effects of urbanization on Mountain Chickadees.