Studies of learning mechanisms critically depend on the ability to accurately assess learning outcomes. This assessment can be impeded by the often complex, multidimensional nature of behavior. We present a novel, automated approach to evaluating imitative learning. Conceptually, our approach estimates how much of the content present in a reference behavior is absent from the learned behavior. We validate our approach through examination of songbird vocalizations, complex learned behaviors the study of which has provided many insights into sensory-motor learning in general and vocal learning in particular. Historically, learning has been holistically assessed by human inspection or through comparison of specific song features selected by experimenters (e.g. fundamental frequency, spectral entropy). In contrast, our approach uses statistical models to broadly capture the structure of each song, and then estimates the divergence between the two models. We show that our measure of song learning (Song Divergence) is well correlated with human evaluation of song learning. We then expand the analysis beyond learning and show that Song Divergence also detects the typical song deterioration that occurs following deafening. Finally, we illustrate how this measure can be extended to quantify differences in other complex behaviors such as human speech and handwriting. This approach potentially provides a framework for assessing learning across a broad range of behaviors like song that can be described as a set of discrete and repeated motor actions.