When Fox News, under the auspices of 24 co-creator Joel Surnow, set out nearly a decade ago to create a “rightwing Daily Show” it was billed as a destination for viewers unenthused by the satirical, liberal musings of Jon Stewart and Bill Maher, who were then making comedy gold of George W Bush’s foibles.

Surnow, one of Hollywood’s few outspoken conservatives, told Variety at the time that “the other side hasn’t been skewered in a fair and balanced way” – an observation shared by many on the right as Alec Baldwin prepares, with the orange-dusted skin and the blond pompadour, for the upcoming 43rd season of Saturday Night Live. With the aim of filling that vacancy, Surnow and Fox created The Half Hour News Hour in 2007. They brought on Kurt Long and Jennifer Robertson, who’d sit at a desk not unlike that of SNL’s weekend update and skewer the likes of Al Gore, Dennis Kucinich and Rosie O’Donnell. Often, they’d bring on guests proffering expertise in a given subject – terrorism or immigration, for instance – or act out skits lampooning purportedly liberal preoccupations like sexual harassment and global warming.

“An Aeromexico flight arrived to the US with 12 passengers complaining of cramps, nausea and chills, mainly because they were hiding in the wheelwell,” Robertson once quipped.

Or, when the House reached a deal to fund the war in Iraq, Long’s on-screen persona Kurt McNally called it “the biggest Democratic collapse since Nancy Pelosi’s facelift gave out”.

And when a fake sexual assault expert joined the hosts to explain the ways in which men, not women, were the victims of workplace harassment, she proceeded to smother McNally’s face between her breasts as he peered toward the camera and said, “Yeah, awful.”

The Half Hour News Hour lasted just one season, and instead of opening the floodgates for rightwing satirists, became the worst-rated show, at the time, in the history of the review-aggregating site Metacritic. Since then, efforts to create a rightwing variant of The Daily Show have been unsuccessful, while late-night comedy’s liberal stranglehold is reupholstered by ever-more partisan voices like Samantha Bee, Trevor Noah, John Oliver and Stephen Colbert.

Meanwhile, rightwing comics, or even those of a centrist breed, have been left with the scraps of talk radio, a medium less conducive to comedy than it is towards the inflammatory rhetoric of hosts such as Rush Limbaugh and Alex Jones.

But late-night’s liberal monolith often works against itself, its hosts appearing, to all except those of a certain political persuasion, as preachy vehicles of indoctrination, limousine liberals shouting into the void. In turn, anyone who’s turned on a television in the past 15 years might infer that conservatives, or conservative comics, just aren’t funny.

This, of course, is not the case; humor itself has no political allegiance. It was Trump, after all, who campaigned on a kind of Don Rickles-esque insult comedy, his excesses disguised as showmanship, his prejudices as performance. Trumpism, too, exposed not just virulent strains of nativism in the electorate, but an appetite for politics as entertainment, for a mordant “straight-talker”, the right’s very own Jon Stewart. And if ever there was a time for rightwing satire to thrive, it would appear to be now, in a tribalistic political climate some attribute to the blind partisanship of media organs like Fox News, Saturday Night Live and, as Caitlin Flanagan wrote in the Atlantic, late-night television.

So why hasn’t it happened? Rightwing comics, the genre’s personae non gratae, are looking for answers.

“Close your eyes and picture a conservative,” Michael Loftus, a rightwing comic, proposes. “It’s some big, fat, balding white guy smoking a cigar and counting his money. Once you start saying ‘conservative comedy’, people don’t believe you. It’s like Sasquatch or the Loch Ness fucking Monster. There’s such a stigma, so everybody goes: this must be hate speech.”

Loftus himself hosts a syndicated talkshow called The Flipside, the most prominent attempt at a rightwing Daily Show since Fox News’ Red Eye, the airy, irreverent 3am offering from Greg Gutfeld, which was recently cancelled in favor of Tucker Carlson Tonight reruns.

On The Flipside, which can be found on YouTube or in the 5.30am time slot on the Family Entertainment Network, Loftus is quizzical but restrained, operating out of a mostly nondescript Dallas studio adorned with quotes by Groucho Marx, Joe Strummer and the vaudeville performer Will Rogers, suitable accessories given that Loftus likens conservative comedy to the counterculture: “It’s a lot like when I was in a punk rock band in high school,” he says.

In a gag about Hillary Clinton called the Benghazi dance – “you can dance if you want to, you can leave your friends to die” – the host is cheeky and natural, though observably hamstrung by a lack of resources and the network on which the show airs.

“It was safer than I wanted to play it,” Loftus explains. “But there was a part of me that just wanted the show on the air, which felt like a victory.”

Victories, for conservative comics, are hard to come by. Outside the brick walls of comedy clubs, where their politics are unfashionable but not blacklisted, and churches, where many faith-based performers have cut their teeth, rightwing comics have found themselves battling a bureaucracy whose gilded gates are famously difficult to pry open.

“I’m the new Lenny Bruce,” Brad Stine, a conservative Christian comic who’s been likened to Sam Kinison and George Carlin, told me. “That’s how ridiculous this is. They’re not arresting me like they did Lenny; they’re just not allowing me on their TV shows.”

Stine is a born-again Christian, a label that makes up one-third of the existential trifecta (white, male, Christian) that he considers the primary blockade in his efforts to join the ranks of the comedy elite. Before what he refers to as an awakening – when a lesbian standup at a comedy club advised him not to shy away from politics in his act – he appeared on mainstream networks such as MTV, Showtime and A&E, and was almost booked for the 2004 Republican national convention. Embracing his politics earned Stine a nice living on the comedy club circuit but made him a pariah on mainstream networks.

“I’m used to being made fun of as a Christian and a conservative,” he says, adding that critics of his, many of whom he considers a part of the “leftist” media apparatus, are more likely to call him unfunny than they are to attack his politics. “It’s McCarthyism lived out in real time, because when Chris Rock does the same thing I do, it’s called social commentary.”

Loftus, for his part, doesn’t believe there’s some industry-wide conspiracy – “I don’t think Hillary and George Soros are meeting with TV Guide plotting how to dominate the entertainment industry,” he told me – but many of his conservative comic brethren, including Stine and Evan Sayet, who regularly inveighs against what he calls the culture-created feedback loop of academia and entertainment, believe more sinister forces are at play.

Sayet, a former writer for The Arsenio Hall Show and Bill Maher’s Politically Incorrect, sees Bush’s election as a clear inflection point in political satire, where polarization in the body politic gave network executives and late-night writers greater incentive to produce the sort of swashbuckling, mostly partisan commentary that made The Daily Show so successful.

“All of a sudden this idiot from the oil patch, the stupidest who has ever lived, beats Al Gore,” Sayet says. “There suddenly becomes this divide, and in that divide you’ve got entertainers and academics and politicians who couldn’t be centrist any more. The executives had to enter the culture war too, just for the sake of getting along with your neighbors Les Moonves and Susan Sarandon and Sean Penn.”

When Sayet pitched his comedy special, Evan Sayet’s Right to Laugh, to executives at Showtime, he became convinced the industry was less about drawing dollars and eyeballs, as conventional wisdom dictates, than advancing its “liberal agenda”.

“I created a comedy special and we took it to Showtime,” he explains. “I’ll tell you exactly what they said to me: this would probably be the highest-rated show in our history, but we’re not going to do it because it would damage our brand.

“If you believe Hollywood cares about ratings and money, then something seems amiss. How could they not have spent the last eight, 10, 12 months capitalizing on this audience? The truth is, they have so much money they don’t really care.”

But if cable news is any indication, the media has capitalized, if not in the way Sayet would like. As Madeleine Smithberg, who created the The Daily Show and is often credited with discovering both Jon Stewart and Stephen Colbert, puts it: “Because people cover the Trumpisphere as if it’s straight, the entire media has become one giant satirical show, and in a way you can’t tell the difference between CNN and The Daily Show.”

Academics such as Alison Dagnes, who examined the politics of satire in her book A Conservative Walks into a Bar, have offered theories regarding what makes conservatism anathema to comedy. Dagnes, and Saul Austerlitz, who teaches a course on television comedy at New York University, posit that successful satire takes aim at institutions, those who govern them being frequent subjects of ridicule. Conservatism, then, largely deferential towards the status quo and composed mainly of straight, white men, is in ideological disharmony with what’s been deemed, by networks and audiences, at least, “good satire”.

“It seems relatively clear that when it comes to political comedy, there’s a built-in preference for the agitated, liberal point-of-view,” suggests Austerlitz. “Maybe there’s something about conservatism that makes the idea of poking fun at our leaders, or the ruling ideas of the day, as being inappropriate or out of bounds.”

If a rightwing comic were to break the left’s ironclad grip on late-night, Smithberg thinks it would’ve happened during the Obama administration. She adds, though, that the personalities of presidents Clinton, Bush and Trump – their accents and blunders so shrewdly parodied by Frank Caliendo, Will Ferrell and Alec Baldwin, respectively – have been more hospitable to satirists: “Colbert was floundering, they were thinking of moving James Corden to 11.30pm, but all of a sudden Trump emerges and through that Colbert is given a focus, a raison d’être.”

“If someone emerged from YouTube, a staunch conservative with a huge following, that person would have a show in five minutes,” she adds. “Showbusiness wants eyeballs. If there’s an audience, and the talent to make it happen, it would be on the air. But Obama was tricky. Of course people took him down, but he was black, and more subdued. In order to laugh about politics, people often have to reach the point where they’re in the fetal position.”

Loftus, who praises rightwing comics like Gutfeld and Dennis Miller, thinks a wave of conservative satire is “bubbling under the surface”. But future efforts to bring a right-leaning voice to late-night would be well advised to learn from the failures of the Half Hour News Hour, a show that, in its express purpose, was designed to level the ideological playing field. In turn, the jokes were often complacent and trite, as if written by a politician trying to be humorous rather than a humorist trying to be political. “I don’t care for anybody that uses their craft as a comic to preach at me,” says Chonda Pierce, a Kentucky-born standup who performed at Trump’s inauguration festivities. “I go to church for that.”

The show called to mind Trump’s own standup routine at the Al Smith Dinner in October, a 70-year-old compulsory campaign stop where the candidates from the two major parties are encouraged to poke fun at themselves and each other. A line about Hillary Clinton being too corrupt for the Watergate commission bombed, as did one about Clinton “pretending not to hate Catholics”.

Where he did score was a mildly self-deprecating joke about Melania Trump plagiarizing Michelle Obama’s speech at the Democratic national convention, much like Barack Obama scored – and perhaps turbocharged Trump’s quest for the presidency – when he poked fun at birtherism by showing the Lion King nativity scene at the 2011 White House correspondents dinner.

It was at that same dinner, five years earlier, that Stephen Colbert, playing the rightwing blowhard of The Colbert Report, famously said “reality has a well-known liberal bias”. He and Bush, he said, give people the truth, “unfiltered by rational argument”. If Colbert’s schtick was his way of mocking the excesses of Republican politicians – “I’m appalled to be surrounded by the liberal media that’s destroying America,” he said at the dinner – then Trump’s election brought things full circle, turning what was once a late-night gag into a kind of prophecy.

In that way, rightwing comics must contend with not only the presumption that their very existence is an oxymoron, but with a president who is, himself, a sort of 24/7 late-night host, his brusque distortions and comic stylings magnified by the ultimate bully pulpit. “What would a conservative comedian say that Trump doesn’t already say?” said Austerlitz. Smithberg agrees: “These comics are working with their hands cuffed.”

Nevertheless, they’re chomping at the bit to make satire of our political reality, waiting for a network to provide them the resources afforded their liberal peers.

“It’s a stacked deck,” Stine says defiantly. “But if you gave me a television show tomorrow, stocked the audience with conservatives, and gave me 20 writers from Harvard, Yale and Brown, I’d be a genius too.”