This tax season, H&R Block attempted to court young taxpayers with a series of web advertisements called “The Hipster Tax Sessions With Kenny Mayne.†The first installment opens with a shot of the 54-year-old ESPN personality decked out in thick-rimmed red glasses, a scarf, a knit hat, and jeans that are supposed to be of the skinny variety but are actually just straight-leg. Mayne goes on to explain that he had once been a hipster and, even though he grew out of that phase, he has made it his mission to teach hipsters about taxes. Cut to Mayne in an empty black room, talking taxes with a bunch of young people dressed in what I imagine a “Hipster†Halloween costume will look like in 20 years. Watching this all play out in a predictable ham-fisted way, your mind might drift to imagine a group of real copywriters clustered around a conference table, high-fiving each over the ad, saying, “We nailed it!†And in a way, they did — if they’re referring to having driven the final nail into the coffin of hipster-as-punch-line.
I have argued that this lazy subset of comedy — so often leaning on a generic “blah blah blah blah hipster†setup or emphatic cuts to creatively hirsute individuals in scarves and fedoras — has been approaching exhaustion for a while,and now, in 2014, it’s gotten there. But partly in spite of and because of this hackneying, a new, better, more lived-in hipster joke arose like a phoenix from the ashes of oh-so-many American Spirit cigarettes and redeemed not only hipster-based comedy but also potentially hipsters themselves.
2003: The Hipster Field Guide Era
The word hipster, coined in the 1940s, has always been used pejoratively, but it didn’t achieve punch line status until the ’90s, when Kramer was called “a hipster doofus†in a 1993 episode of Seinfeld. By 2003, it emerged as a go-to joke, but one that was still primarily confined to articles in publications covering cities with indigenous hipster populations (see New York’s 2002 piece on the ironic rise of crack in Williamsburg). The release of Robert Lanham’s The Hipster Handbook (and, to a lesser extent, Josh Aiello’s A Field Guide to the Urban Hipster) sought to introduce this emergent subculture to outsiders, specifically as something to be laughed at. Structured as a guide, the cult book pioneered the hipster joke structure — list stereotypes, call people hipsters, laugh, repeat — that would be replicated in many forms of media over and over, for more than a decade. The Hipster Handbook is where, as a graduating high-school senior, I first learned of this species of human person. I remember thinking that cool older people were laughing at hipsters, and I also remember the first time I laughed at hipsters, too, that summer in the U Street neighborhood of Washington, D.C. Ironically (but not really) sold at stores like Urban Outfitters, the book was still too insular to be the punch line’s watershed moment.
2007: The Hipster Joke Goes Online
Like The Hipster Handbook, the early viral video sketch “Hipster Olympics†(embedded below) uses a faux-Olympics framing device to do little more than rattle off the existing stereotypes of stuff hipsters liked circa 2007: tight pants, ironic T-shirts, vinyl records, MySpace accounts, etc. That was pretty much its entire reason for existing. It wasn’t conceptually inventive, but “Hipster Olympics†was hugely important in the evolution of the hipster joke because it brought the concept of making fun of hipsters to the internet (and more important, to teenagers). Released just as YouTube and Facebook had become viral-ready, “Hipster Olympics†was the right video and the right subject at the right time, even if its creators, POYKPAC, didn’t see it that way. As one of the sketch’s writers and stars Ryan Hunter told me a few years ago for another story, the day of shooting, they saw the cover of Time Out New York, which read “Why the Hipster Must Die.†They thought it was over, when in reality, it was just beginning.
2009: The Rise of the Generic Hipster Joke
Boy, was it ever. “Hipster Olympics†begat so many imitators that it was difficult to escape them if you spent any time online in the late-’00s. We consumed a seemingly endless procession of web sketches and image-macro riffs on the theme: “Hipster Tea Party“; “Hipster Shore†(like Jersey Shore, but hipstered); “Hipster Disney Princesses“; “Hipster Disney Princesses – The Musica“; “Hipster Thanksgiving“; “Hipster Interrogation“;  â€The Hipster Games“; “The Hipster Song“; “Hipster Hitler†(like Adolph Hitler but hipstered), and so on and so on and so on and so on. The descendants of “Hipster Olympics†effectively ushered in what we’ll call the “hipster generic†punch line, where, as I’ve written before, the jokes were constructed as if using Mad Libs, with every blank asking for “hipster stereotype.†As such, this punch line is basically listing and pointing. The “hipster generic†became a meme, which necessitated endless repetition.
2011: The Hipster Joke’s Mainstream Moment
On September 19, 2011, 2 Broke Girls premiered in prime time on CBS, of all places, armed with the most trite of punch lines. From the pilot on, 2 Broke Girls used its Williamsburg-Greenpoint setting as an excuse for seemingly endless “hipster generic†sight gags and lines like this one: “Hipsters in Williamsburg will pay anything if it makes them feel like they’re ‘in’ on something new that no one else knows about. All you need is a gimmick.†Woof. That is not a joke. It’s just a mean, hack observation. This peaked in a scene where Kat Dennings played “Hipster or Homeless,†which felt like a years-old joke, because it was. 2 Broke Girls wasn’t the only offender: Take, for example, the May 2011 episode of ABC’s Happy Endings, in which Penny (Casey Wilson) goes out with a hipster. In the episode, Max (Adam Pally) teaches Penny how to be a hipster, by slipping giant glasses on her face and teaching her rules like “only like things ironically,†so she can fit in with a girl who “has a blog about zines†and a guy “who won the mustache contest three years in a row,†both of whom are dressed in that same Halloween-like costume. These aren’t characters based on real people — they’re characters lazily reverse-engineered from a collection of clichés. It was also around this time that “hipster†became a stale joke and buzzword for less-hip print publications — check out any trend story in the New York Times from the last three years and you’ll get the idea.
At this point, hipster jokes were rendering the term almost meaningless. Talking with Billboard in 2012, Portlandia’s Carrie Brownstein remarked on her own confusion: “Is it a way of dressing? Is it a lifestyle? Is it about the possessions somebody owns? Is it because they have a beard … because there are so many kinds of beards!†“Hipster,†according to Brownstein, had become a flexible term, subjectively used to label things “people are a little bit threatened by.†She gets at something essential: You know a hipster when you spot one, so long as that hipster is never yourself. I recently asked a bunch of hipster-leaning friends if they thought of themselves as hipsters (which I don’t recommend doing, people don’t like being asked that). They all paused and said “no†with caveats like “I don’t go out enough†or “I’m not enough of a nerd†or “my clothes are too nice†or “my clothes aren’t cool enough†or “I floss — hipsters don’t floss.â€
It’s the result of hipsters not being a single subculture anymore (if they ever were), and instead a subjective pastiche of parts of many subcultures. By breaking through to the mainstream via CBS sitcoms, YouTube videos, and the overall exposure to indie rock music and hipster fashion advertisement by The O.C.s and the American Apparels of the world, what used to be confined to 20- to 35-year-olds in various fringe neighborhoods of coastal cities, is now entrenched across all age groups throughout the country (if not the world). And so the “hipster generic†joke changes depending on who’s telling it: To people living in Williamsburg, only the smelly kids in Bushwick are hipsters; to the rest of Brooklyn, hipsters are the people living in Williamsburg; to the rest of New York City, hipsters are the people living in Brooklyn; to the rest of New York state, hipsters are the people living in New York City; to much of America, hipsters are the people living in coastal states like New York. There is always someone defining hipster more broadly than you do. For example, Fox News Channel mainstay Greg Gutfeld’s new book, Not Cool: The Hipster Elite and Their War on You, hipsters are anyone who is pro-choice, anti-gun, etc. The irony is that Gutfeld is most definitely the chief hipster of Fox News. Stereotype-based humor suffers when the group being made fun gets more and more broad — think of any terrible race-related joke you’ve heard. The reality is that, by now, we are all hipsters, and that’s a pretty large group to point at and say every one of us does X and every one of us wears Y.
2011: The Arrival of the Hipster Specific
Just as one form of hipster joke was imploding, another arrived to redeem it. Portlandia’s first episode aired on January 21, 2011, and, although it took a while to break through, it ushered in what we’ll call the “hipster specific†punch line, a joke that explores actually observed, unique behaviors of real people. The show is built out of the world that co-stars and co-creators Carrie Brownstein and Fred Armisen are very much a part of, so the comedy never feels cheap, and is frequently hilarious. Over the course of the show’s four seasons, there are so many examples: “Ordering the Chicken,†“Put a Bird on It,†“Tailgating a Prairie Home Companion,†“We Can Pickle That,†“Fart Patio,†“Anti-Corporate Student Art,†“Smoothie Bar,†“The Best Part Is Going Home,†and so on. (Non-Portlandia examples of “hipster specific†comedy pieces include SNL’s Wes Anderson parody, “Bein’ Quirky,†Key & Peele’s “Noice,†The Daily Show’s exposé on the Park Slope Co-Op, College Humor’s “Baristas are the Ultimate Male Fantasy,†Above Average’s “HBO’s Girls Tour.â€) Take the pretty perfect sketch “She’s Making Jewelry Now,†which takes an observed trend — people who make and sell handmade jewelry on Etsy and at hip flea markets — and turns it into a trenchant character study. The big difference here is that Portlandia wasn’t mocking hipsters as a whole. They weren’t saying all hipsters do this – they weren’t even saying the word hipster at all. Instead, it’s focused, looking at acute absurdities of hip, alternative, urban, indie culture, which outsiders might label “hipster.â€
2012–14: Hipster Characters
The natural and important extension of the “hipster specific†has been the rise of hipster characters. This includes the women of Broad City, Jess on New Girl, and, most prominent, Hannah on Girls. (There have definitely been hipster characters in movies, but they tend to be in movies too small to make mainstream noise, i.e., everything starring Greta Gerwig.) You might not like these characters, but they’re undeniably realized and the “hipster generic†can’t stand up to them. Even 2 Broke Girls has sharpened a bit here. Realizing the show couldn’t sustain the same broadness for more than a season, this year they put Max in a surprisingly cute relationship with Deke (Eric Andre), a secretly rich hipster dude who lives in a tricked-out dumpster. It’s not that the “hipster specific†took the place of the “hipster genericâ€; it’s just that precision presents a strong contrast to the ever-bloating definition of what and whom a hipster is. All these “hipster specific†characters are making the “hipster generic†feel like a strawman wearing a scarf and thick-rimmed glasses.
Last night’s season four finale of Portlandia, like previous finales, focused on the show’s recurring characters, as opposed to freestanding sketches. Specifically, it intertwined stories about the feminist bookstore owners, nature enthusiasts Kath and Dave, and the overly earnest, somewhat bohemian Peter and Nance. Sure, none adheres to the strictest definition of hipster, yet they each contribute to the gestalt picture that is Portlandia and, in turn, Portland — and, in turn, hipsters as a whole, if you’re no longer willing to view the word with a negative frame. And I think you are, because for years you’ve seen the alternative. You don’t have to love or even watch Portlandia; there are and will be other options for jokes about that corner of society, because true specificity doesn’t get old. I expect we’ll see more fully realized hipstery characters on shows next season and you’ll probably like at least one of them — you hipster, you. Did you hear Greta Gerwig is going to be starring in and writing on How I Met Your Dad? It’ll be on CBS.