A system and method providing interactive content representations enabling content sharing are disclosed. In general, a content representation that is descriptive of content made accessible by a hosting user is presented in association with a content representation host representing the hosting user. The content representation host may be, for example, an avatar in a virtual environment, a custom webpage of the hosting user, an identifier of the hosting user in a peer-to-peer (P2P) network, an identifier of the hosting user in a mobile network, or the like. Based on the content representation, a viewing user can determine whether content of interest is accessible from the hosting user. The viewing user may interact with the content representation to further explore the content made accessible by the hosting user and, if desired, initiate transfer of at least some of the content to a client device associated with the viewing user.