This report tries to pinpoint what the slippery word hipster means by untangling each of the four eras of hipsterdom and how they changed over time. To do so requires looking back at the origins of hipsters in the 90s when Americans were granted digital access to culture just as the service economy encouraged us to commodify our lifestyles. We recount the rise and fall of the companies that defined this lifestyle –from Pitchfork to Vice Magazine to American Apparel– to understand the relationship between hipsters and their corporate representatives. With the onset of social media, hipsters found it necessary to represent themselves and were heavily influenced by the Hipster Runoff and Party Photographers. From here, we look at the public’s hatred of hipsters for real and imagined reasons. Finally, a description of the mid-2010s transition from The Hipster of yesterday into The Activist of today and what the Indie Sleaze revival says about both.