When the predictable umbrage over white rapper Macklemore’s appearance in an apparently anti-Semitic stage costume broke out this week, my first instinct was to leave dumb enough alone. But gradually I began to feel more like the late Peter Falk as Columbo, pausing at the threshold of an exit door as an important query about a case slowly forms in his mind.

In the Macklemore caper, neither the charges nor the perpetrator’s alibi seemed to add up. Yet at the same time, this latest minor incident of idiocy-in-entertainment pointed to a wider pattern, a cultural crime spree that’s been going on in America for centuries—one that never seems to get nearer to being solved.

The Internet collectively face-palmed last weekend when photos were released of Macklemore wearing what looked like a stereotypical old-Jewish-man costume, complete with false hooked nose and beard, in a surprise show at the EMP Museum in his hometown of Seattle. Worse, the Grammy winner was performing his hit “Thrift Shop” at the time, which made it seem like he was wisecracking about cheap Jews and retail schmattas.

I’ve never thought Macklemore particularly savvy, but the idea that he deliberately went out in anti-Semitic costume seemed out of character. While neither his songs nor his persona appeal to me, what’s usually annoying is how painfully earnestly he strains to show what a sensitive, enlightened, big-hearted bro he is.

Most famously there’s his straight-dude-touting-gay-marriage anthem “Same Love,” which he performed at the Grammys while dozens of same-sex couples in the hall were joined in matrimony. But he’s also one of the few white rappers who’s admitted feeling conflicted about his racial position—in his early song “White Privilege,” he fretted about appropriating and “gentrifying” hip-hop: “I give everything I have when I write a rhyme/ But that doesn’t change the fact that this culture’s not mine … We still owe them 40 acres/ Now we’ve stolen their 16 bars.” Could this really be the same guy prancing around the stage in a shoddy Shylock outfit?

It took a few days for Macklemore to respond with anything longer than a tweet, but if his eventual statement is anything other than sincere, it’s an improbably masterful execution of a “play dumb” strategy. He explains in awkward prose that he’d just grabbed a random collection of costume pieces—including a “witch nose”—as a disguise, so that he could be unrecognized in the crowd before making his appearance. He describes the costume as one part Lincoln, one part Ringo, or maybe “Humpty Hump with a bowl cut.” He just didn’t realize, he says, that anyone could see it otherwise. Finally he apologizes to those he offended and says (again, rather awkwardly) that the silver lining is now he knows about the “incredible” Anti-Defamation League.

Like the ADL, I mostly buy Macklemore’s plea. It’s estimated that less than 1 percent of Seattle residents are Jewish, and friends in the area tell me they detect a consistent lack of awareness of Jewish issues and culture there. (This essay by Eli Sanders goes into depth.) So it is possible, in ways that seem unbelievable to people in Los Angeles or New York, that no one in his entourage sized up that look and caught any hints of Jew-demonizing medieval Christian woodcuts, Victorian stage caricatures (I flinch to recall myself as a high school junior, acting Fagin with stereotypical mannerisms in Oliver!), or the cartoon propaganda of Nazis and Jewish conspiracy theorists to this day.

Perhaps they should have noticed, however, that the particular costume nose they used was not actually a “witch” nose but, as reported by the Seattle Stranger, a “Sheik/Fagin Nose” (just to make sure all your Semitic stereotypes are covered). Granted, it did come from the same shelf as the witch noses.

Then again, maybe a few of them did note the similarity but not its dark undertones. Which must be the same rationalization that happens when Katy Perry poses as a “geisha” in her American Music Awards performance, or with a grab bag of Orientalism in her “Dark Horse” video, or as unfunny comedian “Yosef Shullum” telling rabbi jokes as in her “Birthday” video (which would be less disturbing if Perry’s preacher father weren’t given to sermons about Jews and their money). Or when Wayne Coyne of the Flaming Lips defends faux Native American costumery for his hipster friends, to the point of firing a band member for disagreeing with him. Or when Miley Cyrus uses a phalanx of twerking black women as stage accessories, and Avril Lavigne does the same with Asian girls.

Are we experiencing a bizarre epidemic of cultural appropriation? I don’t think so. What we’re undergoing is an escalation of awareness now that social media can circulate such images so widely and rapidly—along with critics’ complaints about them, and the backlash to the complaints, and the backlash to the backlash. The cycle can be numbing, and the temptation to indulge in the easy pleasures of condemnation and judgment—wanting not to miss out on joining each chorus of disapproval—tends to reduce all the cases to the same thing. But in fact, Macklemore’s ignorant boneheadedness isn’t alike with Coyne’s arrogant obnoxiousness, and Katy Perry’s ersatz SNL skit shouldn’t be too casually equated with her dad’s sectarian bigotry.

The underlying problem here is that American popular culture always has been a bizarre epidemic of cultural appropriation. One of the ironies of the Macklemore incident for me is that it took place at the EMP Museum, the home of the EMP Pop Conference—the annual gathering of critics, musicians, and scholars where I acquired my deepest education on this very question. In 2005, the first Pop Con that I attended, the theme was “Music as Masquerade.”

The opening night I was startled to be listening to a discussion of blackface minstrelsy not just as an abhorrent racist practice (which of course it was), but also as the very foundation of American pop. Its paranoid and extravagant cross-cultural borrowings, distortions, and mishmashes were direct antecedent to ragtime, vaudeville, Broadway musicals and much more.

In panel sessions over the next couple of days, presenters played recordings, told tales, and showed pictures of all the varieties of ethnic imitation and exaggeration that passed as entertainment on early 20th-century stages, radios, phonographs, and screens. There were “yellowface” enactments of Charlie Chan-style Asian stereotypes, all manner of “Mickface” drunken-sentimental-Irishisms, and, yes, “Jewface”—a concept explored by former Slate pop critic Jody Rosen, who helped curate a CD anthology by that name featuring period music like “When Mose with His Nose Leads the Band” and “Cohen Owes Me 97 Dollars.”

Like blackface, this whole genre of performance is deeply shocking to modern eyes and ears; think of how disconcerting it is to run across its later-surviving remnants in performances like Mickey Rooney’s bucktoothed “Asian landlord” act in Breakfast at Tiffany’s. But in its day, it was all received as respectable, good fun—to the degree that the Jewfaced or yellowfaced performers were often Jews or Asians themselves, joining in with degrees of enthusiasm or reluctance that are often hard to decipher at this remove.

And as all the recent pop-culture cases demonstrate, some version of those racial dress-up games is going strong in modern America. It’s too easy to imagine we’ve progressed that far beyond it. I usually think that if The Simpsons were being created today it would never have made Apu such a “brownface” portrayal of an Indian shopkeeper. But then again, have you seen the Korean boss in 2 Broke Girls, a portrayal Emily Nussbaum in The New Yorker rightfully called “so racist it is less offensive than baffling”?

It’s comforting to fantasize that our tweets and blog posts could shame appropriation and stereotype out of existence, but the boundaries are inherently fuzzy—is it appropriation every time a non-black musician uses a blues scale or a dance beat, or are certain sounds grandfathered in to the common culture after X number of decades? It’s very off-putting to see Perry drape herself in Asian textiles for “exotic” effect, but would we confine her to only certifiably legitimate-white-heritage Swiss maid outfits in future, just to be on the safe side? That’s nearly as gross.

Cultural mixing-and-matching is part of the creative process in music, fashion and many other forms. It’s both American pop culture’s original sin and part of the shameless vitality that’s helped it spread and adapt and evolve around the world. Trying to strike the right productive balance between critical awareness and hair-trigger censure is probably impossible, though that doesn’t mean we should let insult and exploitation pass unmentioned. (I should probably acknowledge at this point that I’m a white, Canadian, Catholic-raised male, so perhaps this is all just too easy for me to say.)

The funny thing is that Macklemore’s blunder here was far from the most interesting allegation of cultural appropriation against him. But usually it’s in the opposite direction, via his excessively self-regarding “appreciation” of cultural difference—to the point, some would say, of usurpation.

He raised hackles in January, for instance, when, having beaten all the black nominees for the Grammy for best hip-hop album, Macklemore sent a text to Kendrick Lamar saying he felt he’d “robbed” Lamar as the rightful winner—and then undermined the graciousness of the gesture by publicizing the text on Instagram. Similarly many queer people (though definitely not all) have complained that “Same Love” is “Acceptance for Dummies,” a straight guy patting himself on the back for his broad-mindedness, while gay musicians’ songs about their own experience still don’t get radio play.

In all these instances, Macklemore—whose stage handle, it’s worth mentioning, is itself a play on blaxploitation-era slang for a pimp—has walked a tightrope between solidarity and theft. There’s no reliable measure for what differentiates sincere alliance from opportunism except our individual “smell” tests—and as we’ve just been reminded, we all have different noses. It’s probably wiser to refrain, for at least a Columbo-like moment, from leaping instantly to righteous indignation, however naive a wish that might be in the digital age.

More importantly, though, it should be a larger part of the culture of entertainment that white performers get schooled enough to realize that their showbiz instincts are inheritances of an industry that produced blackface-loving superstar Al Jolson, Fu Manchu movies and “Mose with His Nose.” Then maybe they would take a harder look in the mirror when pulling a “random” costume out of the collective unconscious, and seek second opinions from aides with a minimum of cultural literacy.

Still, as audiences in this mongrel land we call planet Earth, I think we’re going to have to be prepared to be baffled by racial mix-ups, gaffes, and confusions for a long while yet. As Macklemore himself put it in “White Privilege”: “It’s human nature to want to be part of something different/ Especially when your ancestors are European Christians.”