What is a hipster, and why has this cultural trope become so resonant of a particular mode of artistic and connoisseurial expression in recent times? Evolving from its beatnik origins, the stereotypical hipster today is likely to be a globally aware “creative” who nonetheless fails in their endeavour to be an exemplar of progressive cultural taste in an era when cultural value is heavily politicised. Today, artist memes and hipster memes are almost interchangeable, associated with people who are desperate to be fashionably distinctive, culturally literate or as having discovered some obscure cultural phenomenon before anyone else. But how did we arrive at this situation where elitist and generically “arty” connotations are perceived in so many cultural forms? This article will attempt to provide an historical context to the rise of the contemporary, post-1990s, hipster, who emerged out of the creative and entrepreneurial ideologies of the digital age – a time when artistic creations lose their alternative credence in the markets of the creative industries. Towards the end of the article “hipster hate” will be examined in relation to post-critical practice, in which the critical, exclusive, and in-the-know stances of cultural connoisseurs are thought to be in conflict with pluralist ideology.