The development and widespread use of Internet technologies and platforms that are grouped under the labels "Web 2.0" and "social media" have led to celebratory accounts of their potential as tools to unleash human creativity. A "creativity consensus" has emerged that describes a vision of creative production via these new platforms as universal, democratic, communal, non-commercial, and revolutionary. The avant-garde of Web 2.0 creativity are said to be young, web-savvy media makers: a new generation that has embraced new technology and is upending old notions of creativity and related cultural practices. This dissertation challenges these views through an ethnographic investigation of deviantART, the self-described "world's largest online art community." The dissertation demonstrates how conflicting ideals of art, creativity, and the web, when put into practice, shaped the site as ideological and technical infrastructure for creative practice and the formation of members' creative identities. In their use of the site, participants in deviantART actively, and at times contentiously, engaged with historical tensions concerning both art and the web. The dissertation explores tensions emerging around three sets of concerns: (1) gaining artistic recognition through visibility, popularity, or quality; (2) demonstrating artistic "seriousness" in relation to ways of improving at art; and (3) controlling and circulating work through the concepts of property, "sharing," and "theft." The dissertation argues that rather than upending Romantic conceptions of art and creativity, the web uneasily accommodates multiple conflicting ideologies. Intersecting with tensions in art are tensions around the web and its overlapping corporate, commercial, and communal uses, deviantART brought together a diverse set of art worlds and creative practices via a seemingly conventional set of interfaces, features, and functionality. In turn, participants on the site helped manifest, reproduce, and transform these tensions in art practice and web use. These findings illustrate flaws in conventional accounts of creativity in a world with the web—accounts that fail to recognize the active, contested, and ongoing work underlying the mutual production of creative practice and the web.