Proceedings of the WebSci'09: Society On-Line, Athens, Greece, (18-20 March 2009)Little to nothing has been written about the origins of Flickr, one of the first and most successful tagging Web Services. However, looking back on its early stages of development, one learns that in its first incarnation it used to be a massively multiplayer online game playable through the browser entitled Game Neverending (GNE). After some releases, the game per se was dropped and its tools later evolved into what eventually became Flickr, the photo-sharing website especially famous for its innovative implementation of tagging. With now more than 54 millions visitors since its inception, such unquestionable achievement immediately raises deep questions regarding to the motivations users had to adopt this service. While such a transition between a MMORPG and a tagging system is quite unique, it is nevertheless tempting to analyse it according to a hermeneutical grid that would insist on the peculiar ludic dimension it inherited from video games - thus providing the basis for an understanding of tagging systems as ludic systems. Treading this path is a required step to underline some of the most prevalent aspects of (but not limited to) the so-called Web 2.0. Namely, that the limits between work and play are more and more blurred thanks to the ludic engagement of entire communities of users that technical platforms aim to elicit and even hoard. As similar applications become everyday more ubiquitous, new social and ethical concerns arise. Moreover, it might not be the most effective way to produce what we call “people–powered structured content” (PPSC) either, just as Flickr demonstrated when it implemented triple tags under the guise of machine tags. What this example indicates is that users who retain the possibility to innovate are those who’re not kept behind closed interfaces; they may further more have, at least on a practical level, a better grasp of what tags really are than researchers..