Research has shown that processing dynamics on the perceiver's end determine aesthetic pleasure. Specifically, typical objects, which are processed more fluently, are perceived as more attractive. We extend this notion of perceptual fluency to judgments of vocal aesthetics. Vocal attractiveness has traditionally been examined with respect to sexual dimorphism and the apparent size of a talker, as reconstructed from the acoustic signal, despite evidence that gender-specific speech patterns are learned social behaviors. In this study, we report on a series of three experiments using 60 voices (30 females) to compare the relationship between judgments of vocal attractiveness, stereotypicality, and gender categorization fluency. Our results indicate that attractiveness and stereotypicality are highly correlated for female and male voices. Stereotypicality and categorization fluency were also correlated for male voices, but not female voices. Crucially, stereotypicality and categorization fluency interacted to predict attractiveness, suggesting the role of perceptual fluency is present, but nuanced, in judgments of human voices.