This thesis gives a definition and chronology of city pop and places it within the context of Japanese history. City pop can be traced from the 1960s folk movement in Japan until its demise in the early 1990s, coinciding with the end of the bubble economy. This thesis also examines the mid-2010s resurgence of interest in city pop among English-speaking internet users, beginning with a nostalgic rediscovery and curation of city pop around the turn of the century by DJs in Japan known as “crate diggers.” City pop was then transmitted to the West through sampling in hip-hop and especially within the internet-based genre of vaporwave. The character of vaporwave is one of dystopia and is highly contrasted with the breezy, optimistic sound of city pop. City pop was eventually discovered in the late-2010s by a wider international audience through YouTube, largely due to the suggestion algorithm and the sudden popularity of Takeuchi Mariya’s “Plastic Love.” This thesis will define nostalgia in relation to music and show in what ways it has been present as a factor throughout the history of city pop.