The transformation of the "hipster" from straw man to bogeyman has been a gradual process: here's a first, incomplete draft of this supremely important cultural history.
1988 - 2009: Ironic sunglasses, popularized by Kim Gordon of Sonic Youth and kept in the cultural consciousness for 21 years by the likes of Scott Weiland and Kanye West, infuriate everyone.
1988 - 2004: Punk-rockers, alt-rockers, anarchists, academic punks et al gradually abandon their teenage obsessions, grow wider in girth, and get jobs as adjunct professors or IT drones. Circa 2002, these aging alternatypes come to realize that their cultural offspring are having sex without of dogmatic critical theory hangups ruining said sex and are listening to techno music, which Jello Biafra (insert other dated counterculture hero here) once told them was the enemy. This group, coming to realize its own cultural irrelevance and advanced age, recoils in jealousy.
1998-2009: Aging libertarian goths who work in information technology and spend their days perusing 4Chan realize in horror that those arty "queers" they made fun of in high school have grown up and make money working in fields that confound their computer science-centric sensibilities. To make it all the worse, these "hipsters" are invading their precious Internet.
2000: Dave Eggers releases A Heartbreaking Work of Staggering Genius and is hailed as the greatest author of a generation he is 20 years too old to be a member of. Generation in question buys copies of the book en masse, only to find that it is not very good, and quietly comes to resent itself for the literary excesses of a man 20 years its senior.
2001-2008: Vice Magazine, American Apparel and softcoreporn party-photo blogs enter the cultural consciousness, taunting most of the world with a fantasy bacchanalian lifestyle of drugs and easy sex available only to the most entitled of the Williamsburg elite, incensing the other 99.85% of the world.
2003-2009: Due to the iPod and iPhone, Apple becomes a market force once again, infuriating ASP.net/MSFT-certified network workers who find their technological hegemony threatened. As a result, they take to the Internet to demonize Mac users. Apple chooses to exacerbate this cultural rift with a series of smarmy commercials identifying Mac users as an obnoxious Zach Braff-wannabe and PC users as an asexual nebbish.
2004: George W. Bush wins a second term in office. Veterans of the WTO protests in Washington etc determine that their cultural offspring's ignorance of cultural studies doctrine are to blame.
2004: Zack Braff stars as a painfully precious indie rocker in the romantic comedy Garden State, reminding popular culture that smug, painfully earnest assholes have continued to exist in the years since R.E.M. fell of the cultural radar.
2005: Republicans, jocks, and bankers discover the Internet outside of sports or economy sites. Once they are run off of every respectable blog comment section for calling all other users "faggot" or "gay", they regroup and determine that "hipster" is a convenient euphemism.
2006: Thanks to Michael Pollan and Oprah, yoga moms increasingly adopt a vegetarian or vegan lifestyle. Meat-eaters look up from their plates of half-masticated pig flesh and determine that these yoga moms must be mocked out of cultural relevance.
2006-2009: Employees of the banking and marketing sector accelerate the bankruptcy of the term "hipster", as they come to apply it to individuals that have never previously been described as such, such as baby-boomer icons Garrison Keillor and Ira Glass. Infinitely tone-deaf, this group derides all individuals between the ages of 20 and 50 who do not drive vehicles that cost six figures as "hipsters".
2006: Valleywag launches, and uses "hipster" as a shorthand for any PHP/Rails coder/Internet start-up owner who is 1) white 2) under 50 and 3) wears JJ Abrams glasses.
2006: Subcultural strife! Libertarian Internet start-up owners and fixed-gear-riding anarchists find themselves competing for shared resources of housing and anonymous sex in the Mission and Williamsburg; new internecine subcultural conflict begins. Rest of world conflates the two groups, despite their diametrically opposed political and cultural affiliations.
2006: Gawker adopts hipster-bashing as one of its primary topics. Since Gawker is written and edited by white, alcoholic, creative professionals with liberal arts degrees from elite Ivy League schools, this represents the apex of the snake-eating-tail phenomenon in which alleged hipsters vilify others for alleged hipster status while loudly protesting that they, themselves, are not hipsters.
2007: Metalheads discover the Internet outside of black-metal messageboards and promise ruin upon all that oppose them.
2007: Neil Pollack releases his "damn it feels good to be an entitled knowledge-worker" tome, Alternadad, offering a cultural manifesto for creative professionals who dress their children in Ramones t-shirts like Victorian dolls, in one final gasp at relevance.
2008: A generation of creative professionals settles into its role as the smug, entitled rebirth of the Baby Boomers. Some members of said generation, now working in the advertising industry, use indie rock music or DIY art-inspired visuals to deliver their pitches. Arugula-eating black man Barack Obama becomes President. Middle America looks up from its Costco Chicken Bakes in horror and grasps for a by-now-shopworn insult.
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Quick note of clarification in response to a couple of comments: the usage of "faggot" in this piece refers less to its usage as a way of stating "you are a gay homosexual, and I find that threatening," so much as its schoolyard-taunt usage, which is more of a rear-guard expression of the sentiment, "you dress/do/believe in ways that are unusual to me, and I find that threatenening, and therefore I will compare you to a gay homosexual, whom I also find threatening."
