In this paper, I will examine an evolutionary hypothesis about musical expressiveness first proposed by Peter Kivy. I will first present the hypothesis and explain why I take it to be different from ordinary evolutionary explanations of musical expressiveness. I will then argue that Kivy’s hypothesis is of crucial importance for most available resemblancebased accounts of musical expressiveness. For this reason, it is particularly important to assess its plausibility. After having reviewed the existing literature on the topic, I will list (...) five challenges the hypothesis is supposed to meet. Although my list of challenges does not aim at exhaustiveness, I believe that the hypothesis must meet all of the challenges I suggest if it is to work as a cornerstone for a theory of musical expressiveness. (shrink)