There is no doubt that mediation has become a central issue outside formal music education. An outstanding example of this is digital music and its dependence on the new technologies of production, dissemination, and consuming. In this paper, the author argues that (1) mediation is one of the most important aspects of digital artistry and that (2) the pedagogical implications of recognizing this are significant concerns to music educators. He also discusses two examples that he hopes exemplify those ways in which digital artistry has been at the center of musical-cultural transformation for decades and that new educational possibilities can be found from the ways in which musical meaning is processed in the digitalized culture. Even though his examples will pertain to popular music, the author hopes to show that they also have more extensive implications over genre lines. (Contains 12 notes.)