In this article we propose a reading of “Dead End Street”, one of the most successful songs of one of the most popular British pop groups of the 60s, The Kinks. However, we will not discuss the song as such, but its remediation as a music video (a practice that did not have to wait for MTV to make its appearance in mass media culture). The analysis will briefly contextualize the group, the song and the clip, but its major objective is to use the Kinks example to open a new question in the larger debate on intermediality and transmediality (the twin notions that represent for us the essential aspects of remediation and convergence culture). The article will start with some terminological clarifications, before moving to its central question, which has to do with the rhetoric and the aesthetic aspects of intermediality and transmediality (and this move is strongly relying on McLuhan’s thinking on “hot” and “cool” media and their respective impact on the audience). On the one hand, it is no longer possible to avoid these mechanisms if one wants to be commercially successful. On the other hand, certain techniques of intermedialization and transmedialization may have a negative impact on the intrinsic power and quality of a given work, as we demonstrate by the close reading of “Dead End Song.”