“I’m bad,” the conceptual poet Vanessa Place told an interviewer recently. For those who define poetry as the compression of the maximum meaning into the minimum number of words, Place’s statement might just qualify; those two words, “I’m bad,” are doing a lot of work.

If you’ve heard of Place at all (and you probably haven’t), it’s for the controversy surrounding one of her projects: tweeting the entire text of Margaret Mitchell’s Gone With the Wind over the course of six years. In 2015, an anonymous group of poets calling themselves the Mongrel Coalition Against Gringpo took offense at this work and, particularly, at Place’s use of an image of actress Hattie McDaniel—costumed as Mammy, the role she played in the 1939 film adaptation—as her profile photo. They accused Place, who is white, of donning “blackface” to present a project that may pretend to critique Gone With the Wind but in fact “reinscribes that text’s racism.” Their campaign for her to be dropped from various gigs, appointments, and conferences succeeded, culminating in the Whitney Museum’s cancellation of Place’s scheduled performance of an unrelated work, Last Words, composed of the final statements of executed inmates, that summer.

“For many years, I have made it a practice never to explain or apologize for my art,” Place wrote in an artist’s statement she apparently felt obliged to issue in 2015. “I am primarily known as a conceptual poet who often appropriates language that isn’t mine: my primary medium is the situation.” She certainly got one of those. Place contended that her original intention had been to prod Mitchell’s famously litigious estate into suing her for copyright infringement so that she could use the publicity to call attention to both the novel’s enduring popularity and its racism. And maybe that’s true, but if so, the Mitchell estate did not take her bait. The Mongrel Coalition did.

The outsiders’ creed that art must speak the unspeakable truth runs deep in contemporary culture.

It was a statement Place made to the Guardian newspaper that crystalized, to me, the mismatch between her artistic approach and the present cultural moment. “I see art that’s sanitized, art that’s precious, art that’s playing safe, art for the market,” she said. “People say they want transgression, that they’re looking for the radical edge, but I’m not so sure.” This surprised me, because while I can certainly remember a time when people called for and praised “transgression” in art and literature, it’s been awhile. The word has the stale odor of an old leather motorcycle jacket, now cracking at the elbows and shoulders, that once sheathed its owner during forays through punk bars and performance art venues. It’s a word redolent of the 1990s, when conservative Christian officials argued that the National Endowment for the Arts ought to be shut down rather than allowed to fund artists whose work was described by one Texas Republican as “patently offensive to the average person.” In those years, causing offense was a badge of honor for artists, proof of their renegade status and a sign that their work had cut deep and drawn forth a fundamental, uncomfortable truth, something that made even their own audiences squirm, at least a little. Is there room for that firebrand attitude anymore, now that outrage is a routine feature of public life? Could it be that artistic transgression, like East Village squats and mohawks, has become completely and hopelessly passé?

The belief that art ought to be transgressive, that one of its roles is to desacralize whatever the “average” person reveres, has much earlier roots than the 1990s, of course. “Épater la bourgeoisie” was the motto of the French decadent poets more than a hundred years ago. Middle-class culture and society were so banal and repressive, the thinking went, that the only pathway to creative greatness and freedom lay in deliberately outraging them. This was an ethos carried forward by movements like Surrealism and Dada, which Place sometimes cites.

Épater la bourgeoisie has traditionally been the prerogative of young artists; Place is 50. When she was in her 20s, four performance artists—John Fleck, Tim Miller, Holly Hughes, and Karen Finley, known as the NEA Four—stood at the center of a maelstrom. Their work became the focus of a successful right-wing campaign against federal funding for individual artists, particularly those deemed indecent and offensive by conservatives.

“Indecent” in this instance meant either works dealing with explicit LGBTQ themes, as was the case with Fleck, Miller, and Hughes, or explicit depictions of rape, incest, and the female body, which was Finley’s purview. In 1990, NEA chairman John Frohnmayer vetoed the grant applications of all four artists in the aftermath of controversy over the agency’s funding of exhibitions of homoerotic photographs by Robert Mapplethorpe and of Piss Christ, a photograph of a crucifix submerged in urine by the Catholic artist Andres Serrano. This was a prominent battle in the culture wars, and it continued throughout the decade. In 1999, then-Mayor Rudy Giuliani threatened to cut off funding to the Brooklyn Museum over an exhibit featuring a painting by Chris Ofili, a Nigerian-British artist who incorporated elephant dung and images clipped from pornographic magazines into the work. The funding cuts would have closed the museum down. Multiple lawsuits, protests, rallies, op-eds, and think pieces followed, as they had on behalf of Mapplethorpe and the NEA Four. In the 1990s, free speech was the rallying cry of the artistic left.

If all of this uproar seems a bit parochial in an era that sees white supremacists cozily ensconced in the White House, remember that it happened against the background of the AIDS crisis, an epidemic many leading politicians refused even to speak of publicly if that meant acknowledging homosexuals as human beings Americans ought to care about. The belief that homosexuality is disgusting, immoral, and against God’s will—all reasons social conservatives found the contested art indecent, that is, unspeakable—was literally killing people.

What is transgression if not the violation of “decency,” the fearless unveiling and celebration of what is “patently offensive to the average person”—in other words, to the good ol’ bourgeoisie, who for generations could reliably be shocked by displays of sexuality, irreligion, and disobedient, messy womanhood? Sometimes the pleasure artists and their audiences take in transgressive works is sheer naughtiness, as the career of film director John Waters gleefully demonstrates. But more often than not, art that courts offense claims to be presenting a truth about human beings, their bodies, and the world that polite society prefers to deny. How urgently that truth needs to be told may vary with the historical moment, but the outsiders’ creed that art must speak the unspeakable truth runs deep in contemporary culture.

Finley’s notorious performances often involved smearing her naked body with foodstuffs while, for example, narrating the threats of a subway rapist (“I’m an Ass Man,” delivered with incandescent rage) or recounting the molestation of a little girl. I remember finding her off-putting at the time, even as I supported the NEA’s right to give her a grant despite the disapproval of Holy Rollers. So much transgressive art seemed thirsty to me, desperate to get a rise out of anybody. But perhaps the failing was mine. Looking at a video of Finley in her prime, performing I’m an Ass Man at Limelight, I’m impressed by her intensity, the feeling that she might drive herself off a cliff in the end, taking the audience with her. This is the fury that fuels the #MeToo movement, a fury I experienced myself. How did I not recognize it?

Possibly I was just too shocked, even if I would never have admitted it. Finley’s raw, bizarre rituals both embodied and purged that particular fusion of desire and disgust that men impose on the female body. But shock can backfire. Finley’s sensationalism overshadowed the content of her work and became all that anyone knew or remembered about her performances. She had plenty to say about what it means to live in a woman’s body, but to the average person, then and now, she was little more than an occasion to make jokes about chocolate syrup and yams.

This is the tradition Place alludes to when she asserts that “people” say they want “transgression” in art. But who these people are and what sort of transgressions they claim to desire is unclear. The bourgeoisie is not so easily riled anymore, and like the Margaret Mitchell estate, the Christian right can’t be counted on to rise to the occasion, either. Is principled transgression relevant, or even possible, in the current cultural climate? What are the truths of which bourgeois propriety now forbids us to speak? Place thought she was breaking some kind of rule with her Gone With the Wind project, but she didn’t hit the target she ostensibly aimed for. Her statement maintained that she wanted “to white out Gone With the Wind, to foreground its ‘unfit associations’ while enacting and inculpating the role white women have performed in minstrelsy.” Instead, the group whose oppression she says she intended to illuminate decided that she was part of the problem, not a trickster art magus bent on exposing it.

To be transgressive, Vanessa Place must have a false piety to rebel against, even if she has to invent it.

Place’s new book, You Had to Be There: Rape Jokes—a collection of exactly that, scraped from Reddit and similar online enclaves—feels like safer ground for her; issuing provocations on rape, she can’t be accused of appropriating or furthering the suffering of an oppressed group to which she doesn’t belong. Place told Observer interviewer Helen Holmes that she became interested in rape jokes in 2012, when comedian Daniel Tosh suggested that an audience member ought to be raped for interrupting his act to protest a joke he made on the subject. “There was a debate online,” Place elaborated, “about whether you could tell a rape joke, or whether anybody could. And the conclusion was that no one could, because rape jokes aren’t funny. I remember at the time thinking, Oh, that’s interesting, because they are.” The idea that any online debate ever reaches a conclusion, or even a consensus, is absurd, but even interpreted in the loosest possible way, this, too, is untrue. Prominent feminist commentators allowed that while it’s entirely possible to make a funny joke about rape, most of the jokes being defended were not, in fact, funny, because they sided with rapists. Nevertheless, to be transgressive, Place must have a false piety to rebel against, even if she has to invent it.

The gags Place has collected in You Had to Be There aren’t very funny either, although this is because, being the work of amateurs, they aren’t well-executed. (The only one I laughed at is this, which is at least competently structured: “I was walking in a dark wood and found a recently raped woman unconscious on the ground. Which was when I knew I was walking in circles.”) I didn’t, it’s true, find the jokes Place has collected upsetting, but I did find them depressing. That’s because most of them depend, for their effect, entirely on the belief that their subject matter is forbidden. That is, rather like Place’s work itself, they lean too hard on transgression in the absence of any other apparent skill or insight. The same can be said for the bootlegged recording of a recent set by disgraced comedian Louis C.K. His former adeptness at teasing out the paradoxes and absurdities of 21st-century life has vanished, replaced by crude, bleating, predictable screeds on political correctness and penis size; their only appeal, if it can be called that, lies in the thrill of imagining how much they will scandalize somebody else.

The Korean-American artist Cathy Park Hong identified the fundamental hollowness of Place’s shock value in a 2015 blog post linking the Gone With the Wind appropriation with a widely deplored public reading of Michael Brown’s autopsy report by the white conceptual poet Kenny Goldsmith. Place’s and Goldsmith’s “antics” left Hong frustrated, she wrote, because “we are called upon to respond, to react. I am sick of reacting because yet again, we have been relegated to the role of chorus. Even if Goldsmith or Place is being put on trial, as their defenders like to accuse us of doing, they are still the center of the drama.” Like a sexual exhibitionist (Louis C.K.’s fetish), Place and Goldsmith crave the narcissistic pleasure of being naughty.

Place is right about one thing: There is a similarity between a joke and rape. Both are transgressions. “The structure of a joke, according to Freud,” she wrote in Artforum International, “is that it is a sudden discharge of repression, often sexual, often kind of obscene. And so, in that way, the joke itself ends up being structured, or ends up having the same structure, as a rape—a violent discharge of repressed sexuality.” A joke is a violation, not of another person’s body and self, but of expectations. The man who finds the rape victim in the woods isn’t about to save her from a monster; he is the monster. We also laugh (even if mirthlessly) at the conclusion of a minor escapade or tense encounter, like teenagers after pulling off a shoplifting foray or two friends marveling over the rudeness of a shop clerk. It’s a release of tension, a tension that sometimes arises from the difference between what we want to do and what we ought to do, and also from our disbelief at how flagrantly the rules have been broken. Laughter is the sign that a transgression has occurred, even if that transgression isn’t especially funny.

You can’t have transgression without rules, however, and that is why I’m telling you so much about Place, an artist who intrigues me despite not being very good. Sometimes when you’re trying to sort out an aesthetic distinction, bad art, because it is so typical, is clarifying; good art is all exceptions. What rules did Place break? Were they the same sort of rules broken by the NEA Four, who spoke about gay desire and the female body with an unprecedented frankness (at least in government-funded art)? Much of what transgressive art rebels against is politeness, but politeness has many dimensions. It may dictate that you never swear or discuss sex, religion, or politics in “mixed company.” And it also decrees that you don’t use racial slurs when referring to groups you don’t belong to. The first restriction, however practical it may be, would strike a lot of people as a prime example of phony bourgeois manners, ripe for skewering in the defense of truth. The second example feels like another, more fundamental standard of decency and morality, and breaking that rule a very different way of being bad. The first is a strategy for not offending people; the second, a policy of not hurting them.

Transgressive artists and comedians have an age-old tradition of violating the first kind of politeness in order to say what they feel needs to be said, but only recently have both been called upon to make acute distinctions between this and the second kind of politeness. It isn’t always easy to do, partly because, in some circles, phony bourgeois manners now include prohibitions on overt displays of racism, sexism, and other prejudices, whatever the bourgeois people speaking may actually believe.

Place’s recent projects and Louis C.K.’s bootlegged set both come across as stunted reactions to what seems to them an equally stunted set of new prohibitions, exacting strictures dictating precisely what to say in order to avoid being exposed as holding the wrong attitudes. To people accustomed to viewing themselves as rebels, and their rebellion as a force of liberation, this rankles. But allowing your work to become purely a reaction to those rules is equally confining: Louis C.K.’s new act was as utterly predictable as the “boring” young people he now complains about. The two imperatives are interdependent, locked together in a tedious pas de deux in which all they do is refute and therefore define each other, reiterating the same boilerplate positions over and over again.

The desire to break out of this stifling call-and-response routine is understandable, and there’s something in each of us that yearns to defy a rule. So Place’s celebration of transgression, while currently unfashionable, doesn’t seem entirely obsolete to me: I want art that tells me something I haven’t already heard a dozen times before. But—and here is what both Place and Louis C.K. miss—the alternative to a straitjacket of overly familiar, pious messages isn’t a reflexive return to the even more familiar and hateful ones, however ironized.

“It’s like the inverse of Nanette,” a critic friend said when I told her about You Had to Be There. We’d seen Hannah Gadsby’s one-woman show together in a small theater before it was released as a Netflix special, so we went in without an inkling of what we were about to experience. The show begins as a stand-up routine, not a form I’ve ever much liked. OK, this again, I thought. But then Gadsby cracks open the formula, demanding that her audience ask itself what it expects to see when it pays to be made to laugh by someone like her. Nanette is a transgression—that is, it’s a joke, but a joke on jokes themselves, most powerful when it is least funny. At times, you can’t tell whether you’re laughing at something humorous or out of a need to release the tension of Gadsby’s confrontation.

This came as a complete surprise to me, something that doesn’t happen much anymore. Gadsby demands more from her form than it is in the habit of giving, forces it to accommodate the sort of material that it usually denies. Nanette isn’t shocking, but then shock is both harder to achieve now and a lot less revelatory than it used to be. Gadsby’s show is discomfiting, as complaints from old-school comedy fans about its lack of funniness demonstrate. (In that way, Nanette cuts close to the bone not despite but because of the fact that it has streamed into millions of American households, alongside episodes of Friends, reaching a much wider audience than the transgressive art of the past.) In my eyes, Gadsby is a truer heir to artists like the NEA Four than Place, with her lazy provocations. It is still possible to break the rules in a way that’s fresh and unnerving; you just have to search harder for the right rules to break.