Young songbirds draw the source material for their learned songs from parents, peers, and unrelated adults, as well as from innovation. These learned songs are used for intraspecific communication, and have well-documented roles for such functions as territory maintenance and mate attraction. The songs of wild populations differ, forming local “dialects” that may shift over time, suggesting that cultural evolution is at work. Recent work has focused on the mechanisms responsible for the cultural evolution of bird songs within a population, including drift, learning biases (such as conformity and rare-form copying), and selection (including sexual selection). In many songs or song repertoires, variability is partitioned, with some songs or song segments being stable and consistent, while others vary within the population and across time, and still others undergo population-wide transitions over time. This review explores the different mechanisms that shape the cultural evolution of songs in wild populations, with specific reference to a long-term investigation of a single population of philopatric Savannah sparrows. Males learn a single four-segment song during their 1st year and sing the same song thereafter. Within this song, the buzz segment is a population marker, and may be stable for decades – variant forms occur but eventually disappear. In contrast, the middle segment is highly variable both within the population and over time; changes in relative prevalence of different forms may be due to cultural drift or a rare-form learning bias. Within the introductory segment, a high note cluster was replaced by a click train between 1982 and 2010, following an S-shaped trajectory characteristic of both selective sweeps in population genetics and the replacement of one form by another in human language. In the case of the Savannah sparrows, this replacement may have been due to sexual selection. In subsequent generations, the number of clicks within trains increased, a form of cultural directional selection. In contrast to the narrowing of a trait's range during directional selection in genetic systems, variation in the number of clicks in a train increased as the mean value shifted because improvisation during song learning allowed the range of the trait to expand. Thus, in the single short song of the Savannah sparrow, at least four different mechanisms appear to contribute to three different types of cultural evolutionary outcomes. In the future, it will be import to explore the conditions that favor the application of specific (and perhaps conditional) learning rules, and studies such as the ongoing song seeding experiment in the Kent Island Savannah sparrow population will help in understanding the mechanisms that promote or repress changes in a population's song.