Percy Shelley famously wrote that “poets are the unacknowledged legislators of the world.” For Shelley, great art had the potential to make a new world through the depth of its vision and the properties of its creation. Today, Shelley would be laughed out of the room. Lazy cynicism has replaced thoughtful conviction as the mark of an educated worldview. Indeed, cynicism saturates popular culture, and it has afflicted contemporary art by way of postmodernism and irony. Perhaps no recent figure dealt with this problem more explicitly than David Foster Wallace. One of his central artistic projects remains a vital question for artists today: How does art progress from irony and cynicism to something sincere and redeeming?

Twenty years ago, Wallace wrote about the impact of television on U.S. fiction. He focused on the effects of irony as it transferred from one medium to the other. In the 1960s, writers like Thomas Pynchon had successfully used irony and pop reference to reveal the dark side of war and American culture. Irony laid waste to corruption and hypocrisy. In the aftermath of the ’60s, as Wallace saw it, television adopted a self-deprecating, ironic attitude to make viewers feel smarter than the naïve public, and to flatter them into continued watching. Fiction responded by simply absorbing pop culture to “help create a mood of irony and irreverence, to make us uneasy and so ‘comment’ on the vapidity of U.S. culture, and most important, these days, to be just plain realistic.” But what if irony leads to a sinkhole of relativism and disavowal? For Wallace, regurgitating ironic pop culture is a dead end:

Anyone with the heretical gall to ask an ironist what he actually stands for ends up looking like an hysteric or a prig. And herein lies the oppressiveness of institutionalized irony, the too-successful rebel: the ability to interdict the question without attending to its subject is, when exercised, tyranny. It [uses] the very tool that exposed its enemy to insulate itself.

So where have we gone from irony? Irony is now fashionable and a widely embraced default setting for social interaction, writing and the visual arts. Irony fosters an affected nihilistic attitude that is no more edgy than a syndicated episode of “Seinfeld.” Today, pop characters directly address the television-watching audience with a wink and nudge. (Shows like “30 Rock” deliver a kind of meta-television-irony irony; the protagonist is a writer for a show that satirizes television, and the character is played by a woman who actually used to write for a show that satirizes television. Each scene comes with an all-inclusive tongue-in-cheek.) And, of course, reality television as a concept is irony incarnate.

For the generation that came of age during Vietnam, irony was the response to a growing distrust toward anything and everything. In the 1980s, academics such as Mark Jefferson attacked sentimentality, and Neo-Expressionists gave sincerity a bad name through their sophomoric attempts at heroic paintings. Irony was becoming a protective carapace, as Wallace pointed out, a defense mechanism against the possibility of seeming naïve. By the 1990s, television had co-opted irony, and the networks were inundated with commercials using “rebel” in the tagline. Take Andre Agassi’s Canon camera endorsement from that period. In the commercial, the hard-hitting, wiseass Agassi smashed tennis balls loaded with paint to advertise Canon’s “Rebel” brand camera. The ad wraps with Agassi standing in front of a Pollockesque canvas saying “Image is everything.” For all the world, it seemed rebellion had been usurped by commercialism.

This environment gave artists few choices: sentimentality, nihilism, or irony. Or, put another way, critical ridicule as experienced by the Neo-Expressionist (see Sandro Chia), critical acceptance through nihilism like Gerhard Richter, or critical abdication through ironic Pop Art such as Jeff Koons. For a while, it seemed no new ideas were possible, progress was an illusion, and success could be measured only by popularity. Hot trends such as painted pornography; fluorescent paint; sculpture with mirrors, spray foam, and yarn were mistaken for art because artists believed blind pleasure-seeking could be made to seem insightful when described ironically.

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Recently, the Onion spoofed an ad campaign in which Applebee’s encouraged hipsters to visit their restaurants “ironically” and middle-aged adults to make fun of hipsters. The parody describes four “with it” young folks “seriously” eating their dinner at Applebee’s while ridiculing the food, service and atmosphere. Behind them sit three sad, middle-aged adults mocking the hipsters, sarcastically saying “because I know who the latest bands are I am too cool to eat a cheeseburger without making fun of it.” Neither group is genuinely happy about their meal or station in life. The Onion’s satire points out that irony and formality have become the same thing. At one time, irony served to reveal hypocrisies, but now it simply acknowledges one’s cultural compliance and familiarity with pop trends. The art of irony has lost its vision and its edge. The rebellious posture of the past has been annexed by the very commercialism it sought to defy.

Early postmodernists such as Robert Rauschenberg broke the modernist structure of medium-specificity by combining painting and sculpture. The sheer level of his innovation made the work hopeful. However, renegade accomplishments like Rauschenberg’s gave way to an attitude of anything-goes pluralism. No rules governed the distinction of good and bad. Rather than opening doors, pluralism sanctioned all manner of vapid creation and the acceptance of commercial design as art. Jeff Koons could be seen as a hero in this environment. Artists became disillusioned, and by the end of the 1980s, so much work, both good and bad, had been considered art that nothing new seemed possible and authenticity appeared hopeless. In the same period, a generation of academics came of age and made it their mission to justify pluralism with a critical theory of relativism. Currently, the aging stewards of pluralism and relativism have influenced a new population of painters, leaving them confused by the ambitions of Rauschenberg. Today’s painters understand the challenging work of the early postmodernists only as a hip aesthetic. They cannibalize the past only to spit up mad-cow renderings of “art for no sake,” “art for any sake,”  “art for my sake” and “art for money.” So much art makes fun of sincerity, merely referring to rebellion without being rebellious. The paintings of Sarah Morris, Sue Williams, Dan Colen, Fiona Rae, Barry McGee and Richard Phillips fit all too comfortably inside an Urban Outfitters. Their paintings disguise banality with fashionable postmodern aesthetic and irony.

Likewise in contemporary fiction, Tao Lin has made a reputation off reproducing disaffected, hipster malaise. In “Shoplifting from American Apparel,” Lin inserts himself as the protagonist Sam, a vegan writer who lives in Williamsburg, Brooklyn. Sam often feels vaguely “fucked” in a generally affectless world of name brands, Gchat and Facebook. He shoplifts a couple times and winds up in jail for a night. Occasionally, he mindlessly mistreats others for a laugh: inexplicably throwing a friend’s drink, hitting someone with a stick, and ordering someone to jump over a bush. The entire narrative is as disconnected from the larger society as the characters are from each other, and therefore it reads as a mimetic rendering of a soulless world rather than satire. New Tao Lins publish every day, feeding the culture’s desire to watch its own destruction.

But David Foster Wallace predicted a hopeful turn. He could see a new wave of artistic rebels who “might well emerge as some weird bunch of anti-rebels… who dare somehow to back away from ironic watching, who have the childish gall actually to endorse and instantiate single-entendre principles… Who eschew self-consciousness and hip fatigue.” Yet Wallace was tentative and self-conscious in describing these rebels of sincerity. He suspected they would be called out as “backward, quaint, naïve, anachronistic.” He didn’t know if their mission would succeed, but he knew real rebels risked disapproval. As far as he could tell, the next wave of great artists would dare to cut against the prevailing tone of cynicism and irony, risking “sentimentality,” “ovecredulity” and “softness.”

Wallace called for art that redeems rather than simply ridicules, but he didn’t look widely enough. Mostly, he fixed his gaze within a limited tradition of white, male novelists. Indeed, no matter how cynical and nihilistic the times, we have always had artists who make work that invokes meaning, hope and mystery. But they might not have been the heirs to Thomas Pynchon or Don Delillo. So, to be more nuanced about what’s at stake: In the present moment, where does art rise above ironic ridicule and aspire to greatness, in terms of challenging convention and elevating the human spirit? Where does art build on the best of human creation and also open possibilities for the future? What does inspired art-making look like?

In the visual arts, an analogous form to recursive irony emerged with non-painting. Magnus Plessen had been the most adept innovator of the style. Four years ago, his work included paintings such as “Ladder,” which was composed of a largely white canvas and an image of a ladder created using blue and brown tape. The few brushstrokes that had been applied were scraped away by a palette knife. His thoughtful pictures of vapidity and antipainting permeated the painting culture until every MFA program included a painter using tape as decoration rather than tool. But instead of resting on the motif and style of a new convention, he now makes paintings that describe creation rather than destruction. His recent work is, dare I say, beautiful. Magnus Plessen moves against the reductive provisional trend he helped create by making increasingly intricate paintings of richer color, form and complexity. His 2013 painting, also titled “Ladder,” is now a top-to-bottom color spectacular of blues, blacks, yellows and purples. Now, the only areas of white are the ladder, rather than vice versa. Feet and hands are now rendered with a sensitive touch rather than being wiped away. He has turned from tiny steps toward nothingness and begun leaping toward eternity.