Following its rise to popularity from 2004 onwards, an increasingly idealistic and dominant conception of platforms, practices, and projects shaped by the Web 2.0  paradigm or the Social Web would emerge and rehabilitate past utopian assertions about the democratizing, participatory, and collaborative potential of the Internet, so as to attractively characterize them as enabling radically empowering forms of online participation by average citizens. In this dissertation, the core features of the affectively charged discourse surrounding this growing media environment are critically examined in order to understand their misleading character and  supportive function within the communicative economy of contemporary neoliberal capitalism and the media apparatus of flexible control strategies that sustains it. Moreover, with the help of critical-theoretical, political-economic, and autonomist theories, this dissertation analyzes a set of representative online media practices driven by users and embodying the individualistic and collective incarnations of the Social Web — such as YouTube-based gameplay commentary videos and fanvid parodies of animated media from Japan along with key examples of media crowdsourcing like the Life in a Day documentary and the Star Wars Uncut remake project. Its analysis of these case studies exposes how the above media apparatus of strategies and decisions increasingly shaping this digital media ecosystem, while encouraging the creative agency of online users, often results in its flexible control by corporate interests and the formation of new forms of power relations, inequality, and exploitation.