The new digital economy seemingly is leading to the disappearance of intermediaries. Externalities and the ongoing comparison of competitors favor dominant players; creators and producers also can distribute their content directly to consumers, bypassing any intermediaries. This movement exhibits some contradictory tendencies though. Online transactions give space to various unforeseen intermediation patterns involving contractual relations, information processing, and customer relations. In doing so, they alter cultural sectors and fundamentally challenge traditional organizations and revenues. This overhaul particularly affects economic actors, selection and creative processes, distribution channels, and cultural practices, as well as production structures. Accordingly, the Internet has had notable effects on the complexity of artistic and cultural markets. Various cultural fields thus reveal the emergence and simultaneous development of different ways to create, produce, make available, and charge for contents—that is, different business models. These unfamiliar intermediations drive reorganizations of cultural industries, because they invent innovative economic terms, restructure common forms of creation and recommendation, prompt new forms of entrepreneurship, and stimulate competition by newcomers. This study scrutinizes all these reconfigurations according to three current developments in cultural industries: the vast increase of available contents, the solid entrepreneurial dynamics in online markets, and renewed business models.