A content server uses a form of artificial intelligence such as machine learning to identify audio content with musicological characteristics. The content server obtains an indication of a music item presented by a client device and obtains reference music features describing musicological characteristics of the music item. The content server identifies candidate audio content associated with candidate music features. The candidate music features are determined by analyzing acoustic features of the candidate audio content and mapping the acoustic features to music features according to a music feature model. Acoustic features quantify low-level properties of the candidate audio content. One of the candidate audio content items is selected according to comparisons between the candidate music features of the candidate audio advertisements and the reference music features of the music item. The selected audio content is provided the client device for presentation.