One hundred years ago, Igor Stravinsky premiered “The Rite of Spring,” igniting a near-riot in the audience. It’s hard to imagine that such a response could be elicited by a work of art, let alone by a ballet based on obscure Russian folklore. A different era, to be sure, but more recent artistic scandals feel only slightly less dated. A mere 16 years have passed since the opening of Sensation, the exhibition of Charles Saatchi’s Young British Artists. The show roused Londoners and incited a media frenzy in 1997, and it sent New York’s mayor, Rudolph Giuliani, into near apoplexy when it arrived at the Brooklyn Museum two years later. Whereas Stravinsky was surprised by the response to his composition and fled backstage, the Y.B.A.s anticipated and openly reveled in the shock value of their work, capitalizing on it both literally and figuratively. Giuliani overestimated the public’s outrage, while underestimating the free publicity accorded by his own convulsions. Lines at the Brooklyn Museum wrapped around the block, and aside from a few fanatics, the mayor’s sanctimony was met with a collective shrug. If the “Rite” was a culmination of artistic transgression, Sensation seemed to many like its death knell.

The start of the 21st century reminded Americans that we were in fact still shockable. 9/11 recalibrated the scale, immediately reshuffling taboos and defusing some of the consternation (and cheap thrills) afforded by “confrontational” art. And yet it also indicated that, despite a century of avant-garde dogma, there might be unspoken limits to our appetite for transgression. When, five days after the tragedy, Karlheinz Stockhausen mused that it was “the greatest work of art imaginable,” most of us recoiled. But while Stockhausen’s tone-deafness was bewildering and indefensible, his comment was not entirely dismissible. The suggestion that 9/11 could be understood as a masterful work of performance art derived from an enduring modernist tradition that has long prized provocation, impudence, and rule-breaking as generators of not only artistic innovation, but potent cultural politics. How do we register our indignation while continuing to canonize, say, the Italian Futurists, who often advocated violence as a form of social cleansing, or André Breton, who defined the simplest Surrealist act as “going into the street with revolvers in your fist and shooting blindly into the crowd as much as possible?” Yes, times were different then, but still.

At present, the conception of art history as a history of transgression is at once entrenched and suspect—inextricable as it is from the political entanglements of the day and the seeming dissolution of clear-cut positions. On the one hand, we require ever-bolder violations in order to be sufficiently provoked; on the other, we look back at a century in which transgression was tragically and repeatedly affixed to rigid ideological belief, arguably doing more to reinforce repressive rules and norms than to upend them. What does it mean to transgress today? What are the stakes? Is transgression an adequate means of dissent and resistance, or is it in some sense inevitably counterproductive? Are certain tactics more effective than others? Should there be limits? Is it more cynical to perpetuate transgressive strategies or to abandon them entirely?

Of course, there’s a difference between rhetoric and acts, art and life. (Both Stockhausen and Giuliani belong to a long line of pontificators on the Right and the Left who have clumsily conflated the two.) Recognizing this distinction, many artists look askance at transgression, even as they acknowledge the power of its mythos. Some reject it entirely, turning a blind eye to the overwhelming complexity of current problems and the intractable contradictions of the contemporary world. Others embrace that very complexity, maintaining art’s consciousness-raising abilities while resigning themselves to the impossibility of resolution, to the notion that we’re always already screwed. Rejecting either/or premises from the outset, these latter artists may be as critical of those who defy taboos in the name of liberation as of those who seek to preserve hegemony. “Alternative” modes—humor, irony, perversion, the grotesque—often become their weapons of choice.

Art must also compete with an increasingly pervasive and permissive mass media—envelope-pushing movies, video games, and television shows, and especially the Internet, with its laissez-faire ethic and instantly accessible archive of transgressive matter. Meanwhile, the art world has become exceedingly professionalized, institutional, technocratic, and market-driven, and contemporary art is more popular and profitable than ever. How defiant can an exhibition with a timed ticket and a one-hour queue really be? When artists seek a Chelsea solo show right out of grad school, and art critics aspire to tenure-track jobs at research universities, what are the prospects for true transgression?

“At present, the conception of art history as a history of transgression is at once entrenched and suspect.”

Such questions—and there are many others—remain vital to artistic practice, audience reception, and the continuous reassessment of art’s purpose and function. The writers gathered here approach transgression from diverse points of view. Some argue that it can be subtle and come from unexpected sources—painting, for instance—thus exposing the restrictiveness of conventional definitions. Others remind us that transgression is always in the eye of the beholder, that there are multiple orders of transgression and counter-transgression that cannot be divorced from institutional concerns, and that society habitually betrays its double standards and intrinsic hypocrisies when reacting. Together, these essays affirm that artistic resistance is always, to borrow Philip Glahn’s words, “intricately connected to the material conditions of everyday experience and the technological means that create it.” Transgression is, as Richard Langston maintains, “often contingent on . . . ways of showing and looking that are endemic to the very status quo it seeks to scandalize.” Indeed, by addressing transgression in its myriad forms, these writers implicitly address its opposing terms, the status quo, the prevalent mores and conditions that are ostensibly violated. This collective examination also draws attention to the middle spaces, the blurry boundaries between theory and practice, art and life, fantasy and flesh, boundaries so often obscured by both conservative admonitions and progressive adulations, by alarmists and advocates alike. I hope that readers will respond by reflecting upon their own thresholds and values, and their views of art’s political potential. If transgression still feels vital today, then its nuances must be detailed, its pitfalls and payoffs clarified, its limits at least provisionally defined. If it seems like a tired subject—passé, overly normalized, or even obsolete—then maybe that’s all the more reason to consider it.