Two years ago, the preppy mall staple Abercrombie & Fitch released a line of t-shirts that paired early 1900s–style caricatures of Chinese men (complete with coolie hats, big grins, and slanted eyes) with slogans like “Wong Brothers Laundry Service—Two Wongs Can Make It White” and “Wok-N-Bowl—Let the Good Times Roll—Chinese Food & Bowling.” The clothing chain then professed great surprise when Asian-American activists cried foul; A&F's pr flack Hampton Carney told the San Francisco Chronicle, “We personally thought Asians would love this t-shirt…. We are truly and deeply sorry we've offended people.” As a result of continued protests, the shirts were eventually pulled from stores (and quickly became hot commodities on Ebay).

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Last year, the pseudovintage clothing and housewares chain Urban Outfitters played a similar game with their line of “Everybody Loves a [fill-in-the-blank] Girl/Boy” shirts; they had the poor taste and even poorer judgment to illustrate the “Everybody Loves a Jewish Girl” shirt with dollar signs. Absent those dollar signs, the tees were little more than a retread of the silly “Kiss Me, I'm [an ethnic group]” t-shirts that have been around for decades. But unlike the shamrocks and rosaries that decorate the Irish and Catholic versions, respectively, of UO's t-shirt, the dollar signs evoke an especially nasty and persistent ethnic stereotype. In response to public protest, UO replaced the dollar signs with hearts, but continues to sell the entire line, the range of which says some pretty interesting things about whom everyone loves: fat boys, but not fat girls; Asian girls, but not Asian boys.

It's no coincidence that UO and A&F are sticking these dubious slogans on shirts that look like they were picked up at Thrift Town. By emblazoning retro-racist words and imagery on shirts that are brand-new yet look well worn, these purveyors of lifestyle culture are trying to have it both ways: stirring up a whole mess of racially charged hoopla (which has made for bad-but-good pr for both chains) while attempting to deflate accusations of racism by making the shirts “ironic” (a misuse of the term in the first place, but that's another story). That is, A&F and UO are capitalizing on the vogue for retro kitsch by shilling not only faux-vintage t-shirts but faux-vintage bigotry as well. It's a clever attempt to claim distance from a literal reading of the shirts, because the companies can always argue that they were trying to make fun of the idea of racism, not of a particular race.

In the big picture of racism in America, offensive ­t-shirts are neither the biggest nor the most blatant ­problem. But their sellers' claims that these products are created with the intention of mocking, not encouraging, racism and bigotry rest on a false assumption that we are all beyond identity politics—and thus we are beyond any implications of hatefulness, so we can all have a good laugh at the very idea of, say, anti-Semitism or anti-Asian prejudice. In a sad sort of way, this post–politically correct “humor” is a measure of the success of the very identity politics it scorns.

It's also notably different from defiantly politically incorrect humor, which revels in its flirting with racism and sexism in the name of free speech, but doesn't argue or imply that we live in a postracist or a postsexist world. All those knowingly crass “Bikini Inspector,” “Master Baiters fly Fishing,” and “If you're already this close, why don't you just give me a blow job?” t-shirts found at beach boardwalks and novelty shops across the country don't lay claim to any ironic distance. There's a difference between these cheesy souvenirs and the supposedly hip product being pushed by A&F and UO, and it's not just in the price point (A&F and UO charge upwards of $20 for their shirts, while the novelty shirts can be had for half that). This distinction may be extremely subtle, but it's crucial: A&F and UO are shilling this stuff in a tongue-in-cheek manner to people they presume will get the joke.

Whether or not the customers do is another matter entirely. As cultural critic John Leland points out in his new book, Hip: The History (Ecco), it's not that easy to control the interpretation of these provocative signs. He's referring here to the complications of the word “nigger,” but he could just as easily be addressing these other manifestations of hip humor:

The meaning changes not merely with context or inflection, but according to who is speaking, hearing or overhearing, and who is profiting. The word nigger on a blank page is deafening but impenetrable. It could signal love, hate, or anything in between. It defies definition not because it lacks meaning but because it has too much.

Carney, A&F's pr rep, defended the “Two Wongs” shirt by assuring the San Francisco Chronicle that “we never single out any one group to poke fun at…. We poke fun at everybody, from women to flight attendants to baggage handlers, to football coaches to Irish-Americans to snow skiers. There's really no group we haven't teased.” Underlying this equal-opportunity offensiveness is the notion that “teasing” an entire racial group by invoking some of its most pernicious stereotypes is no different from making fun of people who like to ski—a notion that willfully ignores the fact that racism and sexism are still very much a part of American culture. This line of defense—“We're all treated equally now, so we had no idea people would be offended!”—is in some ways more insulting than outright bigotry, which at least doesn't hide behind a pretense of equality. The companies can always dredge up an Asian-American or Jewish employee who “loved” the t-shirts, or point to the fact that some Asian-Americans snatched up the “Wong” shirts for their unbelievable kitsch factor, as proof that the gear isn't offensive. But unlike the “Bikini Inspector” or what­ever making-fun-of-skier tees Carney referred to, the “Two Wongs” shirts don't intend to poke fun at the wearer—rather, they mock a population that is perceived to be the other.

In a similar stab at dissembling, David Chang, the creator of the ostensibly satiric board game Ghettopoly, which rewards players for building crack houses and pimpin' hoes, claims that because many ethnic groups are portrayed in the game, the premise isn't racist. When the NAACP denounced the game, Urban Outfitters (which was, of course, carrying it) pulled it from the shelves. But Ghettopoly is still available directly from its creator, who defends the game by declaring that it “draws on stereotypes not as a means to degrade but as a medium to bring together in laughter.” If he survives the lawsuit brought by Hasbro, Chang plans to roll out Hoodopoly, Thugopoly, and Redneckopoly.

The most recent entry in the pantheon of misguided egalitarian “teasing” came this spring, courtesy of Details. For the past year, the magazine has quietly been running a one-page humor column, titled “Anthro­pology,” that compares stereotypes of gay men with stereotypes of nongay but supposedly effeminate men: Gay or guido? Gay or British? Gay or magician? Gay or preppy? Even “Gay or Jesus?” managed to slip under the radar. But when writer Whitney McNally dropped “Asian” into the nongay slot in the April 2004 issue and accompanied it with a random assortment of ­Chinese and Japanese stereotypes, she really got people's attention. Straight and gay Asian-American activists staged protests outside the magazine's headquarters and demanded an apology from Details editor-in-chief Dan Peres. He complied, and indeed, Peres's editor's note in the June/July issue is a fairly humble admission of poor taste:

Sometimes you set out to be funny and blow it. There's a line that should never be crossed in any satire, and Details stepped over that line. I'm embarrassed that it took thousands of ­people—including members of my own staff—to point out the hurtful and tasteless nature of the “Gay or Asian?” piece.

Of course, that mea culpa—which included the half apology “I apologize…to anyone who was offended”—didn't stop him from approving the “Gay or Country Singer?” bit that runs a mere five pages later. (“Whether you worship the Opry or wrestle to Oprah, a twangy set of tonsils will never be lonesome.”) Apparently, that uncrossable line for Peres extends to ethnic groups, but not to sexuality. Details, which has over the past 15 years gone from being a very queer downtown rag to a ­self-consciously metrosexual style book, relies on its hipster legacy to deny that it's being homophobic or offensive in running this series that trades on vapid imagery. Gay men are ­hairless! They like to groom ­themselves with fancy products! They work out! They wear clean, well-fitting clothes! These stereotypes could well stand to be deflated, but Details doesn't pull it off. The setup promises a clever deconstruction of ­stereotypes—and I'll admit at first blush I found the concept funny—but the writing has a desperately grasping tone, the ­categories chosen are so dumb that they're meaningless, and in the end Details ­reinforces the very clichés it purports to send up.

This brand of satire is increasingly pop­ular these days, thanks to the mass-market saturation of cool-kid lifestyle culture. At the risk of sounding like a conservative, Bill Bennett–esque postmodernism hater, I blame this phenomenon on the triumph of hipster misidentified irony, which demands that nothing be taken seriously and people feel immune from criticism because they're being, you know, ironic. It's all made ­possible by the winking insiderness, the self-­congratulatory illusion that the trend-driving hipsters are educated and informed enough to know better or rise above racism or sexism. In fact, these folks claim to be so beyond any sort of prejudice that they can wield ordinarily offensive terms and imagery with impunity: “I've got lots of friends who are gay—not that there's anything wrong with that!—so when I describe something stupid by calling it gay, you know I don't mean it in a bad way.” But this style of usage—whether it's exercised by a schoolyard bully or an urban hipster—still relies on a general consensus that things that are “gay” are not good, or, likewise, that a “cunt” is not a person who is behaving admirably. It would be something else entirely if “gay” were used to mean cool or impressive, but, despite a few isolated attempts, it just isn't.

By now, the progression of name-calling from forbidden to fashionable should be familiar: Disempowered groups, from immigrants to gays and lesbians to people with disabilities, begin to advocate for their full rights as American citizens. In the process, radical activists reclaim derogatory terms—gay, queer, dyke, bitch, cunt, homo, slut, crip, heeb, and so on—and brandish them defiantly in an attempt to dilute their power to harm. The names and identity labels start to be picked up by enlightened friends and allies, who feel privileged to use the terms in the reclaimed manner because they are in on the politics. But inevitably, the terminology dissipates to the broader population, who re-reclaim the phrases in a not-at-all ironic or knowing way—thereby completing the cycle. Of course, most of the folks who toss around words like “queer” or “fob” (fresh off the boat), or repopularized phrases like “that's so gay,” are just as likely as activists and their allies to defend themselves from any accusation of hateful behavior.

And because, like everything else, the notion of “hip” is easily reducible to a commodity, this all-sarcasm-all-the-time lifestyle has become a mass-marketable trend, available at malls from coast to coast. But when so-called irony becomes a tool of marketing—just look at all those goddamned trucker hats!—it loses any claim to edginess and becomes merely a set of quotation marks and a smirk. In its original sense—as subversive humor that adopts a mode of expression that is the opposite of what is intended—irony can be a destabilizing and politicizing force, deliberately playing up the most ridiculous of stereotypes or ideas in order to point out how dumb they are. Details had the opportunity to do this with the “Gay or…” series, but either lacked the political edge and depth of critique to make it happen, or simply didn't care to. In the current political climate, this kind of speech has enormous potential to upset the status quo: The Onion is one of few publications that has been quietly, consistently pulling off political critique through ironic humor for years. But it also has the potential to be widely misinterpreted or, worse, wielded as mere style devoid of content or context.

One of the most flamboyant exemplars of this irony-as-edgy-lifestyle product is Vice, which started out as a free paper catering to the punk/skater crowd in Montreal and has since expanded to become a glossy monthly available across the United States. It has also spawned a record label, several books, and a forthcoming tv show. A typical issue might include articles about what it's like to be a “jizz mopper” in an adult video store and fashion spreads featuring hookers, trannies, and runaway teens. It publishes trademark guides to all of the races, on how to be a whore, and on how to gold-dig. Vice's editors and writers are infamous for freely tossing around in print and in interviews slurs like “nigger,” “fag,” and “Paki,” claiming (as they did in one New York Press article) that because they rag on everyone—and because they are or are friends with blacks, gays, and Pakistanis—they can use these words with impunity. Given that Vice's ­raison d'être is to push the edges of acceptability beyond any reasonable limit (and to push as many people's buttons as possible, all in the pursuit of the almighty dollar), it's not all that surprising to hear them spout off like this.

The same attitude is espoused by comedians like Sarah Silverman, whose use of racial and sexual epithets is a huge part of her shtick. She most notably got into trouble four years ago when she told a joke on Late Night with Conan O'Brien about trying to get out of jury duty: “My friend is like, 'Why don't you write something inappropriate on the form, like “I hate chinks”?'…I didn't want them to think I was a racist, but I did want to get out of jury duty so I wrote 'I love chinks'—and who doesn't?” In a subsequent appearance on Politically Incorrect, after being chastised by watchdog groups like the Media Action Network for Asian Americans, she refused to apologize.

The difference between Silverman and, say, Aber­crombie & Fitch is that Silverman's act is an extreme form of satire intended to expand her audience's comfort zones and to limn the very idea of racism, while Vice, A&F, UO, and their ilk are trying to sell us a range of products that add up to a lifestyle. One could argue that Silverman's racially charged humor rests upon a general understanding that ethnic stereotypes and labels still hold great power; there is at least a hint of political substance behind it, and in some ways her use of ethnic slurs attempts to foreground the racism that often operates in the shadows. The lifestyle shillers, by contrast, try to hang their t-shirt slogans on the myth that those stereotypes are so passé that the very idea of them is laughable. But what A&F and ­company either can't understand or willfully ignore is that if those stereotypes truly held no currency, the joke wouldn't be funny. Mul­tiple interpretations are what allow for the possibility of humor—yet they also sabotage any attempt to control its reception. Somehow, I don't think we're going to be seeing shirts emblazoned with “I'm not a racist but my t-shirt is” or “My grandparents emigrated from a repressive political regime and all I got was this lousy t-shirt” any time soon.

As with most of the issues swirling around identity politics, the question of exactly when these jokes are funny boils down to the question of insiders versus ­outsiders. Comedians like Margaret Cho, Chris Rock, and John Leguizamo hail from marginalized corners of American culture and are more than willing to talk, joke, and tease about it; their outsider perspective allows them to both critique the dominant culture and deflate some of the racial/ethnic stereotypes that are applied to them and their kin. Silverman also touched on this in a December 2003 Vice column (perhaps unsurprisingly, she's a regular contributor) when she wrote:

Most say you can't say “nigger” unless you're black. If you're not, you have to say “nigga,” but I think that's gay (oops, I can't say that). How about you can't say “nigger” or any bad Jew stuff if you're a total fucking douchebag? Who defines which people are douchebags? ME!!!

Silverman's propensity to talk shit for the sake of talking shit obscures what is ­actually an important point: Forget making jokes—who even gets to talk about race (or ethnicity or gender or sexuality), and in what terms? When Cho, in her stage shows, imitates her Korean mother, who speaks broken English with a strong accent, it's funny because Cho is an over-the-top parodist who clearly loves her mother despite their occasionally contentious relationship. But it's also uncomfortable for some non-Asian folks (like myself) to listen to, because we're not sure if we're laughing at a goofy cliché or at a real person. Are we working with the comedian to deflate ethnic stereotypes, or are we merely reinforcing them? Are we laughing at her or with her?

The impetus behind much of this post-pc humor may just be chastised confusion: All the social and civil rights gains made by marginalized folks in upsetting the standard discourse have left a lot of people feeling like they aren't allowed to discuss race or sexuality or gender, let alone laugh at them. For every outcry of racism—including all of the instances mentioned previously—there's a response that suggests we're just being a tad sensitive. “It's a joke!” the standard reply goes. “Why do [Asians/blacks/gays/feminists] always take it so seriously?” The line between humor and offense is slippery, of course, and no one likes being told what they can and can't laugh at. That sense of transgression is a big part of “ironic” humor's appeal. You know it's wrong and maybe a bit mean, but you laugh anyway; that frisson of naughtiness can be addictive. But when that uncomfortable moment between laughter and ­outrage is sold as a hip lifestyle, things get tricky. It becomes, like the word “nigger” on a blank page, impenetrable: What, exactly, are we laughing at here?