This contribution reflects on some chosen aspects of singing, playing and performing as they present themselves at the beginning of the 21st century in a field which is referred to as popular music. The theoretical framing of the present discourse represents postmodernism, especially the work by Zygmunt Bauman and his thesis about the liquid society as a metaphor for the social conditions of beginning of the third millennium, Jean-François Lyotard’s observations about the collapse of the “great narratives”, paradigmatical shifts as implemented by New Musicology and the Popular Music Studies and the musicing approach by Christopher Small, outlining the active character of musical practices. The main aspects explicated refer to the extreme overproduction of cultural artefacts, new reception patters, the excessive commodification and commercialisation of popular music as well as the accelerated digitalisation of the musical field, causing essential changes in all spheres of production, distribution and consumption. New technologies make new ways of making music possible and stipulate postmodern techniques such as de-construction, bricolage, sampling, mixing, and mashup. They also open the way to previously unknown aesthetic worlds of multimedia and Virtual Reality and induce significant changes in the musical perception. Further, several demarcation lines that were believed to be stable before, began to crumble (art versus entertainment; live versus mediated; staged versus authentic; real versus virtual; producers versus consumers) and the lack of new musical impulses is being compensated by retro-trends, revivals and the hologramic re-staging of (dead) artists.