Music is a pervasive element of human culture that plays a significant role in our social interactions and goals. The current research regarding the evolutionary nature of music remains divisive, with several groups making competing claims about whether music is an evolved trait and, if it is, what function it may serve for survival and reproduction. In an attempt to further define the multiple dimensions of the evolution of music, this study focuses on a specific methodology for determining the relationship between improvisational musical ability, cognitive fitness, and sexual attraction. In Part 1 of this research, piano musicians completed working memory tests and provided 30-second recordings of improvisation. These recordings were heard by participants in Part 2 of the experiment, who rated both the music and a random facial image from an independent database paired with each song. The data revealed that perceived quality of music is positively associated with attractiveness, with a significant effect observed in males of moderate baseline attractiveness. Although the relationship between some working memory measures and musical improvisational ability proved not to be statistically significant, auditory working memory span yielded a marginally significant result. The overall results are consistent with a sexual selection theory of the evolution of musical improvisation and suggest appropriate avenues for future research.