This chapter explores the context of Web 2.0 legacy cultures of user-generated content, the crowdsourcing of individual creative talent and the playful creative economies that emerge through those collaborative models in semi-permanent conditions of connectivity. The chapter achieves this through acknowledging the roles of creativity as normative psychosocial expressions of desire and recognition, overlaid with emerging exploitative relations of production in creative economies. The chapter outlines a critical discussion of creativity, evaluating the salience of a number of key thinkers, before moving on to discuss how creativity as a concept, process and act can be distorted through phenomena associated with accelerated and automated ‘filter bubbles’ of opinion in social media feeds. The chapter then concludes with a discussion of collaborative creative freedoms which can establish affirmative senses of community and benign circles of self- and other-regarding in semi-permanent conditions of connectivity. These circles are threatened by exploitation and degradation in Web 2.0 contexts, as well as toxic interest-as-advantage psychosocial competition.