The premise has been asked hundreds of times since November: Will political comedy be funny during an Obama administration? The first waves of responses were logical — conventional satire will have less material since the conventional targets won't be as easy. Then came the counter-intuitive backlash — political comedy will be funnier, or at least the same amount of funny, because comedians will have to come up with new and innovative ways to skewer the next administration.

And now, only days away from the presidential Inauguration and we're left with … what, exactly? A feeling of restless dread for the fate of The Daily Show and The Colbert Report? A general disinterest in the humorous side (if there is one) of electing our first black president to the White House? Or a thankful feeling in our gut that Tina Fey's impression of Sarah Palin never had the chance to blossom as it could have under four years of the Alaskan VP?

Looking Back

Only one other time in recent history has there been such an air of hope and change in the political climate with the ascension of a new administration. Was there anyone who dared mock JFK and his beautiful wife, Jackie-O? Certainly not in comparison with who came afterwards: Richard Nixon with his honking nose, ripe for impressions on the Johnny Carson show and scathing, hilarious portraits by Hunter S. Thompson in his Fear and Loathing on the Campaign Trail. In retrospect, the Kennedy years were a wasteland of criticism in comedy form.

That doesn't mean political satire was nonexistent. In Revel with a Cause: Liberal Satire in Postwar America, Stephen E. Kercher mentions the Kennedys' greatest defense against political satire: their own enjoyment of it. The Kennedys and their administration were frequent patrons to Chicago's famous Second City improv troupe and the early sixties provided a breathe-easier contrast to numerous political descent than the paranoid McCarthy era.

But just because the Kennedys provided a relief to what came before, comedians still knew who was buttering their bread. Historian Christopher Lasch said of this time, "Liberal satire often did little more than reinforce the prejudices of the upper middle-class Americans who enthusiastically supported the Kennedy Camelot." Then again, this era's shows like The Daily Show and The Colbert Report are doing the same in their confirmation of upper middle-class educated Americans belief — that George Bush was a shitty president.

If there's anything we can learn from the satire during the Kennedy years, it's that no one should get too comfortable with politicians, lest they end up in the ethically grey area of having to defend policy choices they don't believe in. Kercher's anecdote provides a grim warning:

Given the support that Stevenson, Daley, and other prominent Democrats gave America's young satirists, it is no surprise that they began to view themselves as unofficial diplomats when they appeared overseas. When a Second City company played London's Establishment Club in late October 1962, they were forced to respond to the left-leaning audience's angry and hostile requests for scenes involving the Cuban Missle Crisis. Del Close, a Stevenson stalwart like Sahl who on the Second City stage in Chicago repeatedly took shots at the Kennedy administration's aggressive anticommunist, anti-Castro foreign policy, took charge of the situation and instructed his colleagues to defend President Kennedy from criticism. In addition to pulling a scene critical of American foreign policy, Close engaged the combative London audience with tart reminders of British failures in the Suez. "I would like to point out," Close likewise told the audience, "that you are also members of NATO and that were are in this together."

Looking Forward

So what about today? Is there a chance that history will repeat itself and satirical news organizations that have become such a boon in the last eight years will risk being silenced in fear of alienating an administration they lobbied so hard for?

Jane Borden, Time Out New York's comedy editor, isn't too sure. "That doesn't worry me at all, actually," Borden tells Jossip. "In fact, the Jon Stewart cabal (Colbert and his writers included) are the most trustworthy pundits in the market specifically because they're irrevocably jaded. Suspicion and resignation have been beaten into them over the years.
And even those members of the team whose crusty exteriors have been cracked by hope are still, first and foremost comedians. Their number one allegiance will always be to the joke." And not Mr. Obama.

But even if comedians aren't pledging allegiance to the president, in the end will there be anything funny about the Obamas?

For now, the laugh industry isn't putting too much hope in the charismatic political messiah becoming too much comic fodder; although all the adoration and hubbub surrounding Barack might make for a good punchline, the man himself is far too cool to properly impersonate or mock. Just look at Fred Armisen's lackluster impressions, where the Saturday Night Live player's biggest caricature of his subject is the way he pauses while answering questions.

Fortunately for us, says Borden, an administration does not run on its president alone, because "there's always Joe Biden, thank god." And luckily for us, there's also Rahm Emmanuel with his second-degree of separation to Ari Gold on Entourage, Hillary Clinton (it's been a decade and no one's run out of jokes yet!), and um, Bill Richardson TBD.

And to remain broad in your focus, you have to allow for the inevitable wave of conservative comedians — yes, they make those — that feel more than up to the task of skewering our next president.

Dennis Miller is already weight-training, one assumes. The Blue Collar Comedy Tour will probably see demand enough for a revival. And hell, the conservative news satire program The 1/2 Hour News Hour that aired on Fox News for a brief period might be brought back and finally get enough viewers to accurately be described as the anti-Weekend Update. If they get new writers.

And blessed South Park? It'll remain stubbornly Libertarian. A recession can't stop its take-no-prisoners of both sides of the political arena.

But for the most part, it's true: The majority of better political comedy is created and performed by liberals, or comedians making liberal-leaning jokes, and in the upcoming four-plus years of Barack Obama's presidency there will be a dearth of those easy jokes and impressions that were the bread and butter of so many comedians for the last eight years.

But if anything, it's a call to arms: Find something funny — fast — or risk a political satire movement headed up by the people who brought you Barack the Magic Negro.