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Soon after Jon Stewart arrived at The Daily Show in 1999, the world around him began to change. First, George W. Bush moved into the White House. Then came 9/11, and YouTube, and the advent of viral videos. Over the years, Stewart and his cohort mastered the very difficult task of sorting through all the news quickly and turning it around into biting, relevant satire that worked both for television and the Internet. Now, as Stewart prepares to leave the show, the brand of comedy he helped invent is stronger than ever. Stephen Colbert is getting ready to bring his deadpan smirk to The Late Show. Bill Maher is continuing to provoke pundits and politicians with his blunt punch lines. John Oliver’s Last Week Tonight is about to celebrate the end of a wildly popular first year. Stewart has yet to announce his post-Daily Show plans, but even if he retires, the genre seems more than capable of carrying on without him. Stewart, Colbert, Maher, Oliver and co. belong to a type of late-night satire that’s typically characterized as liberal, skewering Republicans (and, less frequently, Democrats) for absurd statements or pompousness or flagrant hypocrisy. “The Daily Show, The Colbert Report, Funny Or Die, and The Onion, while not partisan organs, all clearly have a left-of-center orientation,” wrote Jonathan Chait in The New Republic in 2011.This categorization, though, begs the question of why the form has no equal on the other side of the ideological spectrum. Some self-identified conservative comics argue that the biased liberal media hasn’t given them a chance to thrive. Others point out that Obama is a more difficult target than his Republican predecessor: He was the first African-American president, which meant comedians have had to tip-toe around anything with racial connotations, and his restrained personality has made him difficult to parody.

But six years in, Obama’s party has been thoroughly trounced in the midterms and publicly excoriated by right-wing politicians, yet there’s a dearth of conservative satirists taking aim, even though the niche-targeted structure of cable media today should make it relatively easy for them to find an audience. After all, it would have been difficult for Stewart or Colbert to find an audience during the era when three broadcast stations competed for the entire country and couldn't afford to alienate too many viewers. But cable TV news programs need only find a niche viewership. Why then, hasn’t a conservative Daily Show found its own place on Fox? Liberal satirists are certainly having no trouble making light of liberal institutions and societies. Portlandia is about to enter its fifth season skewering the kinds of liberals who don’t understand that eco-terrorism and militant feminism may not be as politically effective as they think. Jon Stewart has had success poking fun at Obama ’s policies. And Alison Dagnes, a professor of political science at Shippensburg University, has found that the liberal Clinton was the butt of more jokes on late-night shows of the 1990s than either George W. Bush or Obama would later be. So if liberals are such vulnerable targets for humor, why do relatively few conservative comedians seem to be taking aim at them?

One explanation is simply that proportionately fewer people with broadly conservative sensibilities choose to become comedians. Just as liberals dominate academia, journalism, and other writing professions, there are nearly three times as many liberal- as conservative-minded people in the creative arts according to a recent study . Alison Dagnes, a professor of political science at Shippensburg University, argues that the same personality traits that shape political preferences also guide the choice of professions. These tendencies just get more pronounced in the case of comedy, which usually requires years of irregular income, late hours, and travel, as well as a certain tolerance for crudeness and heckling.

There are, of course, high-profile conservative comedians in America, such as the members of the Blue Collar Comedy Tour. But these performers, who include Jeff Foxworthy and Larry the Cable Guy, tend carefully to avoid politicized topics, mocking so-called “rednecks” in the same spirit as Borscht Belt acts mocked Jewish culture. When it comes to actual political satire, one of the most well-known figures nationally is Dennis Miller, a former Saturday Night Live cast member who now has a weekly segment on Fox News’ O’Reilly Factor. On a recent show, O’Reilly brought up the Democrats’ election losses, and Miller took the bait. “I think liberalism is like a nude beach,” Miller said. “It’s better off in your mind than actually going there.” His jokes are sometimes amusing, but they tend to be grounded in vague ideologies, not the attentive criticism to the news of the day that has given liberal satires plenty of fodder five days a week. The real problem, Frank Rich wrote about Miller, “is that his tone has become preachy. He too often seems a pundit first and a comic second.” “I think liberalism is like a nude beach,” said Dennis Miller on a recent episode of The O’Reilly Factor. “It’s better off in your mind than actually going there.” The Flipside, a more recent attempt at conservative satire, was launched this year by Kfir Alfia, who got his start in political performance a decade ago when he joined the Protest Warriors, a conservative group that counter-demonstrated at anti-war protests. The Flipside started airing this fall in more than 200 stations across the country, but its growth is hampered by its small budget, according to The Flipside’s producer, Rodney Lee Connover, who said he has to work 10 times as hard because his show has 10 times fewer resources than the liberal shows supported by cable networks.

Connover was a writer along with Miller on The 1/2 Hour News Hour, the first major attempt to create a conservative counterpart to The Daily Show in 2007. It was cancelled after just 13 episodes and has remained the worst-rated show of all time on Metacritic. It was widely panned by critics who complained that it was trying to be political first and funny second, so the jokes were unsurprising and flat. The host of The Flipside, Michael Loftus, says he’s doing the same thing as Jon Stewart, just with some conservative window-dressing. Wearing jeans, Loftus stands and delivers his jokes on a set that looks like the set of Tool Time, the fictional home-improvement show Tim Allen hosts on the sitcom Home Improvement: The walls are decorated with a dartboard, a “Men at Work” sign, and various other items the producers might expect to find in a typical American garage. In a recent episode, after Republicans won the Senate, Loftus sang the song, “Looks like we made it …” to celebrate the victory. But rather than talking about the news, as Colbert and Stewart do, or deconstructing a big political issue, as Oliver does, Loftus frequently makes dated references without offering new context to freshen them up. “What’s the deal with Harry Reid?” he asked in a recent episode. “You either hate him or you hate him, am I right? The man is in the business of telling people how greedy they are, and how they don’t pay their fair share, and he lives in the Ritz Carlton … This guy is literally Mr. Burns from The Simpsons.” Much of his material seems designed to resonate with only the most ardent Fox News viewers. Loftus obviously can’t yet attract the kinds of celebrity guests his network competitors can. But instead of playing games with the guests he can get, he asks softball questions that simply allow them to spout off.

Greg Gutfeld, the host of Fox’s Red Eye, can also be funny, but his willing-to-be-controversial style often comes across as more hackneyed than insightful. “You know you’re getting close to the truth when someone is calling you a racist,” he once said. Gutfeld has also railed against “greenie” leftists who shop at Whole Foods, tolerance, and football players who are openly gay. Gutfeld’s shtick works okay during its 3 a.m. timeslot, but a recent controversy over sexist jokes about a female fighter pilot highlighted just how far his humor is from working in prime time. So if conservatives have yet to produce their own Jon Stewart, it could be the relatively small number of working conservative comedians, or their lack of power in the entertainment industry. Or it could be that shows like The Flipside are failing at least, in part, because they’re just not that funny. But what is it about political satire that makes it so hard for conservatives to get it right?

P olitical humor, in particular, might have an inherently liberal bias. Alison Dagnes spent years looking into this question for her 2012 book A Conservative Walks Into a Bar. She spoke to dozens of working comedians who self-identified as liberals, and as many who identified as conservatives as she could find. One of the reasons she posits for a lack of conservative satire is that the genre has always been aimed at taking down the powerful, from the Revolutionary War through Vietnam and 9/11. “Conservatism supports institutions and satire aims to knock these institutions down a peg,” she wrote.

Theorists have been trying to explain humor as far back as Plato. The ancient Greek philosopher said humor got its power from the pleasure people get when they feel superior over others, laughing at their foibles and flaws. Freud saw it as a cathartic release from society’s repressions, thus explaining all our sex and fart jokes. And Hegel saw it as reconciling two normally incongruous spheres of meaning—i.e., showing a football player in a cheerleading outfit or putting a cat in human clothes. Peter McGraw, an associate professor at the University of Colorado’s Leeds School of Business, has argued for what he calls the “benign-violation theory” of humor. McGraw believes that humor results from violating social norms or by violating a particular person or group. But it only becomes funny when it’s placed in a second context that clearly signals the violation is harmless or benign. In other words, if someone falls down the stairs, it will only be really funny if that person doesn’t get hurt. “Conservatism supports institutions and satire aims to knock these institutions down a peg,” wrote political scientist Alison Dagnes. Earlier this year the journalist Joel Warner published The Humor Code, describing his efforts to test McGraw’s theory. Accompanied by McGraw himself, he visited improv artists in New York and stand-up comics in L.A. The two men talked to the world’s foremost researchers on humor and explored the vast joke collections of humor anthropologists. They even traveled to Japan to see if the benign-violation theory held up in a culture renowned for its (by Western standards) weird sense of humor. In each case, Warner and McGraw were able to use their theory to explain the various kinds of humor they encountered. But when they tried to put the theory into practice, by having McGraw perform standup—first at a bar in Denver and then at the Just for Laughs Festival in Toronto—it didn’t work very well. McGraw did manage to get some laughs eventually, but only after months of immersion and practice.

This attempt to provide an overarching theory of humor suggests that academic explanations aren’t much help to the professionals who are trying to be funny. Humor is a creative art that responds to a specific culture at a particular moment in its history. This response can take many forms: TV sit-coms, internet parody, late-night variety shows, cartoons, stand-up, sketch, improv. But in each case, the jokes only work if they’re perfectly timed and aimed at the right audience.

This struggle to thrive in a particular genre isn’t exclusive to conservatives and satire. At the end of the 1990s, when Jon Stewart took over The Daily Show, conservatives dominated one form of entertainment media: talk radio. Liberals have never managed to equal conservatives’ success in that arena. The Air America network—whose talent included Rachel Maddow, as well as Saturday Night Live alumnus and future Senator Al Franken—filed for bankruptcy at the beginning of 2010. Even MSNBC has never been able to attract as large an audience as Fox News, the televised version of conservative talk radio. Could it be that American political satire is biased toward liberals in the same way that American political talk radio is biased toward conservatives? Dannagal Young, an assistant professor of communications at the University of Delaware, was looking into the lack of conservative comedians when she noticed studies that found liberals and conservatives seemed to have different aesthetic tastes. Conservatives seemed to prefer stories with clear-cut endings. Liberals, on the other hand, had more tolerance for a story like public radio’s Serial, which ends with some uncertainty and ambiguity.

Young began to wonder whether this might explain why liberals were attracted in greater numbers to TV shows that employ irony. Stephen Colbert, for example, may say that he’s looking forward to the sunny weather that global warming will bring, and the audience members know this isn’t what he really means. But they have to wonder: Is he making fun of the kind of conservative who would say something so egregious? Or is he making fun of arrogant liberals who think that conservatives hold such extreme views? As Young noticed, this is a kind of ambiguity that liberals tend to find more satisfying and culturally familiar than conservatives do. In fact, a study out of Ohio State University found that a surprising number of conservatives who were shown Colbert clips were oblivious to the fact that he was joking. In contrast, conservative talk radio humor tends to rely less on irony than straightforward indignation and hyperbole. When Rush Limbaugh took down Georgetown student and birth-control activist Sandra Fluke in 2012, he called her a “slut” in order to drive home his point about state-mandated birth control. After the liberal blogosphere erupted with derision, Limbaugh responded with more jokes, asking that Fluke post videos of her sex online so taxpayers could see what they were paying for. (After a few days, he offered a public apology, insisting that he “did not mean a personal attack” on Fluke.)

These examples formed the kernel of Young’s theory that liberals and conservatives look for and see different kinds of humor. Connover, the producer of The Flipside, has already voiced skepticism about Young’s hypothesis. “That’s another way of saying that liberals are smarter,” Connover said. “And clearly that’s not the case. Liberals are some of the dumbest people to walk the earth.” Young insists that hypothesis is not about intelligence; it’s about a preferred structure of jokes. She maintains that there’s nothing inherently better about liking ironic jokes over exaggerated ones.

O n a recent cold afternoon, a long line of what appeared to be almost entirely white urbanites wrapped around the block several times to see Jon Stewart. The night before, Stewart had been seemingly caught off guard by a grand jury decision not to indict the police officer who choked Eric Garner to death. Most media tiptoed around the issue, giving voice to criticisms of the protesters as well as criticisms of the police. But on this night, Stewart’s satire was savage and unsparing: He mocked the people who worried more about their Christmas shopping than the death of black men, and compared America’s justice system to apartheid.

The people who are most knowledgeable about politics—and therefore, the ones who understand the most political jokes—also tend to be the most ideologically extreme. So it makes sense that political satire shows, like conservative talk radio and its Fox News spinoffs, are ideologically skewed: Their viewers are the kinds of people who know the latest news stories and what their fellow ideologues are saying about them. Comedy Central’s political satire shows have always drawn some of the most liberal viewers on TV. They’re the mirror image of their more earnest conservative counterparts. Before the taping of one of the very last episodes of The Colbert Report, a warm-up comic asked audience members what they did for a living. His question drew predictable responses: artist, lawyer, teacher. Then the comedian came to a gay Broadway financier and his boyfriend who, it turned out, worked on a non-profit trying to help Hillary Clinton win the presidential election in 2016. The man lifted up his shirt and pulled down his pants to reveal a tattoo of Clinton’s signature near his nether regions. Colbert’s fans weren't just representatives of liberalism; they were its apotheosis. Before the start of the show, Colbert took several questions from his liberal tribe, finally calling on me for the last question. “Who is your favorite conservative comedian?” I asked from the furthest row in the back. I wondered whether he’d be able to name anyone. He paused, and for a second of silence it seemed as if he might not have an answer. Then, just before galloping back to his desk to start the show, he responded with an impish smile and a twinkle in his eye: “Bill O’Reilly.” The crowd roared and jeered with laughter.