As musicians, we emphasize exactness in our performances, tempered with "human" attributes such as timbral nuances. Interestingly, the reverse applies to the technology we use, which we program to simulate human performance while maintaining a standard of "mechanical" precision. Notably, the curious coexistence of these scenarios manifests in the Vocaloid community. Vocaloid, a vocal synthesizer program developed by Crypton Future Media, offers a selection of voice banks marketed as "virtual singers. " Some users enjoy the program because it allows them to write music for these virtual singers that is "not possible for a [human] to sing" (Yamada 2017), only to be covered by human singers who faithfully replicate those songs "machinelike" feats. Meanwhile, other users utilize Vocaloids various tools for manipulating virtual singers pitch and timbre, with many aiming to approximate humanlike vocal delivery. Thus, the human artist emulates the virtual singer who pushes human bounds of speed, vocal range, and other facets of performance, while the virtual singer — programmed by the composer but perceived as an independent agent — emulates the human singer in an attempt to bypass its software limitations. In this paper, I share examples that highlight the fascinating products of humans and machines viewing each other as idealized singers, drawing from Deleuze and Guattaris (1987) concept of the "body without organs" (BwO). I aim to demonstrate how artistic expression in the Vocaloid fandom calls into question the divide between human and machine, encouraging the listener to partake of the "pleasure in the confusion of boundaries" (Haraway 1985).