This chapter explores how digital technology, capitalism, and nostalgia have transformed the experience of popular music from the late twentieth century to the present. Through anecdote and cultural analysis, it examines the collapse of temporal distance in music consumption, arguing that the digital archive renders all music contemporary and flattens historical context. Setting up the psychoanalytically-inflected arguments in the following chapters, this chapter discusses how the commodification of music and the rise of streaming services have shifted the meaning of authenticity, rebellion, and innovation, making difference and non-conformity marketable attributes rather than subversive acts. Drawing on theorists such as Mark Fisher, Svetlana Boym, Todd McGowan, and Slavoj Žižek, it analyzes the interplay between nostalgia, fantasy, and the impossibility of authenticity in a culture where the past is perpetually available and the future is commodified.