For me, the most quintessential piece of Y2K1 literature is starring , Tara Reid, Rosario Dawson, Parker Posey, and Alan Cumming. From the inclusion of the Moviefone guy, to the bombardment of corporate sponsors, to the appearance of Carson Daly on MTV’s Total Request Live, it pegs itself to a very specific time in the media landscape. With sung by Letters To Cleo (known for their memorable contributions to 1999’s 10 Things I Hate About You), Josie And The Pussycats prepared teens for the new era of capitalistic consumption fueled subliminal messages in pop music. Not to mention , the cheesy boy band made up of some of the biggest, goofiest leading guys at the time (Donald Faison, Seth Green, Breckin Meyer, and Alexander Martin). It’s a kitschy, overstimulating masterpiece. [Gabrielle Sanchez]