What is a medium? What do media mediate? What is the relationship between media and technologies? Different notions come into play in the definition of media and their overlapping often creates confusion. The delicate relationships between subjectivity, experience and media force a continuous redefinition of personal identity, but in the contemporary world characterised by the adoption of the digital as the sole method of encoding, personal identity and inter-individual relationality appear increasingly dependent on dynamics channelled at the technological level - even before being directed at the social or political level. In this scenario, the results emerging in contemporary art are able to illuminate the relationship between media, technologies and identity, showing how it is possible to implement practices that are autonomous from the paths imposed by technological systems. The solutions adopted by artists often succeed in triggering changes that insinuate themselves into society by hijacking technological developments. Artistic operations offer valuable cues to critically face contemporary challenges and implement workable solutions from below. In an analysis that crosses sociology and aesthetics, Joseph Kosuth engages in dialogue with Marshall McLuhan and Walter Benjamin, while 360° virtual reality is read from the perspective of the 19th-century panorama and the expanded cinema of the 1960s. In addition, social networks are laid bare by the operations of Ben Grosser and the Liens Invisibles, while Dziga Vertov proves prophetic in framing the role of the spectator in the new economy of attention born with the cinema and developed by the Internet, of which Vocaloids (the singing holograms that spread in the 2000s) are the latest expression.