How Did Hipsters Become So Uncool?

No one can agree what the word means, which might explain why everyone insists they're not one.

Hipsters are everywhere these days—and so are the people who make fun of them. Websites like Unhappy Hipsters and Look at This Fucking Hipster attract hordes of finger-pointers, especially at guys like this, with crayons in his beard. People love to make fun of hipster glasses, ridiculous facial hair, inappropriate hatwear, and other signs of being too cool for school and the rest of the planet. But why does hipster humor seem to be, according to my hipster-dar, more prolific than hipsters themselves? And how did making fun of hipsters become so hip?

It isn't easy to define exactly what a hipster is, but that’s not from lack of trying. The Hipster Handbook diagnoses the afflicted as: “One who possesses tastes, social attitudes, and opinions deemed cool by the cool ... The Hipster walks among the masses in daily life but is not a part of them and shuns or reduces to kitsch anything held dear by the mainstream. A Hipster ideally possesses no more than 2 percent body fat.” (My friend Eileen will like that last bit, since she believes that “white men under 5'8", less than 160 pounds form the core of male hipsters.”) A recent Psychology Today piece excerpted Andrea Bartz and Brenna Ehrlich’s book Stuff Hipsters Hate, which defines a hipster as “A creative 20-something who defines him- or herself by a sighing superiority over mainstream society; appears to subsist entirely on pain and art.” Ouch. In an angst-soaked nutshell, today’s hipster is considered a pretentious, clueless jackass.

It wasn’t always so. “Hipster” used to ooze coolness. First, there was “hip,” which once had a sister word “hep”—both were first found in the early twentieth century, meaning "in the know" or "aware." You could be hip or hep to all sorts of information, as in this Oxford English Dictionary 1904 example: “At this rate it'll take about 629 shows to get us to Jersey City, are you hip?” Both words broadened to mean sophisticated and sharp, and then narrowed to mean uber-fashionable. In the 1930s and through the 1950s, “hep” gradually lost the lexical Darwinian struggle to “hip,” but not before producing variations that included “hepcat,” “hep kitten,” and—you guessed it—“hepster.” Mainly, those words referred to people who loved swing music.

“Hipster” first popped up in 1940, and The Historical Dictionary of American Slang’s first use includes the statement that “A hipster never teaches a square anything.” The OED’s early examples include semi-definitions such as “know-it-all” (1941) and “man who's in the know, grasps everything, is alert” (1946). Those descriptions sound groovy, but in the HDAS’s definition of “hipster,” we can find the seed that grew into today’s widespread hipster-phobia: “A person who is or attempts to be hip, esp. a fan of swing or bebop music.” It’s that attempting—especially in clumsy, transparent ways—that make the hipster horrible. The fact that hipness was stolen from black people by white people, and then ruined, supports another time-tested theory: White people ruin everything.

Though “hipster” and “hippy” now seems as dissimilar as a can of PBR and a bong, the words did start out as synonyms. The HDAS’s first use of “hippy” is from 1952, and it wasn’t until the sixties that the word took on its long-haired, psychedelic implications. On Seinfeld, Elaine called Kramer a “hipster doofus.” Other terms, such as “yuppie” and “grup” (a Star Trek-inspired term for adults who won’t grow up), have been modified as “yupster” and “grupster,” word-blends that wed hipsterdom to something equally awful.

Perhaps Jeff Wise said it best when he wrote on the Psychology Today blog, “Nobody likes hipsters, not even hipsters.” In discussing some consumer research, he notes that “people who legitimately enjoy all the trappings on hipsterhood ... must psychologically distance themselves from the demographic group of which they are so clearly a part.” As Wise puts it: “This, then, is the essence of being a hipster. Pretending you aren't one.”

Given the psychological mindgames hipsters play on themselves, I wonder if the whole phenomenon of hipster humor isn’t just another aspect of hipster self-denial. I live in a gentrified Chicago neighborhood, the kind of place hipsters supposedly roam. While I do see some obnoxious glasses and, occasionally, a goofy hat, I don’t see any folks as ridiculous-looking as the specimens on Look at This Fucking Hipster. But even if I did—are they really that interesting? That deserving of so much attention?

My theory: Hipster-hating is the ultimate “He who smelt it, dealt it” situation. It’s a bit like homophobic politicians and religious leaders who inevitably are revealed to be gay as a picnic basket themselves. In other words, if you’re thinking and writing and worrying about hipsters, you’re a hipster.

Oh crap.