The reason cited by most of those involved in the shows is that a fundamental factor is so far missing in Mr. Obama: There is no comedic “take” on him, nothing easy to turn to for an easy laugh, like allegations of Bill Clinton’s womanizing, or President Bush’s goofy bumbling or Al Gore’s robotic persona.
“The thing is, he’s not buffoonish in any way,” said Mike Barry, who started writing political jokes for Johnny Carson’s monologues in the waning days of the Johnson administration and has lambasted every presidential candidate since, most recently for Mr. Letterman. “He’s not a comical figure,” Mr. Barry said.
Now, Jon Stewart has done a pretty good job of doing a la carte mockery of individual screw ups or whatever (as has The Onion), but it's true: there's not really an over-arching Thing that really defines him in the way that traditional comics do and take on a life of their own. Like, say, your average Friar's Club roast. Bea Arthur does not have a dick, but it's a running gag that she does. It defines her totally in the comedy world. Courtney Love is scummy and has diseases, Paris Hilton is dumb, J Lo has a big ass, Tommy Lee has a big dick, etc etc. Jack Benny's cheap. Hugh Hefner is old and uses Viagra. And so on.
So far the late nighters have concentrated pretty much exclusively on McCain's age. Nothing really about his personality. Just he's old. And, as the article brings up, they've been able to make fun of people in Obama's circle. But yeah. The guy is pretty hard to nail down.
Bill Maher says the only funny thing about him in the whole article:
“There’s been this question about whether he’s black enough,” Mr. Maher said. “I have this joke: What does he have to do? Dunk? He bowled a 37 — to me, that’s black enough.”
There is touchiness about the race thing, though and some hesitance for white comics with white audiences to make much of it (the article sounds the alarm for a new era of black political comedy, led by David Alan Grier goddammit nooooooooo).
So this is something to consider, because it is up to us as humorless liberals to find some way to make fun of our sainted puppy dog warrior. It is our duty to make fun of him. After he's elected.
Of course, the right wing reaction to the article is typical and humorless. Or, rather, chock full of "humor". For instance, this from those Laff Technicians over at Newsbusters, saying "I have a joke that some comedy writers can steal and the progressive bloggers will love":
President Bush is extremely unpopular these days. However, one of the
presidential candidates has been aligning himself with the president's policies
and this might be a bad political move for him. Oh, I'm not talking about
John McCain. I'm talking about Sen. Obama's 'move to the center.'
Now.
Dammit, I go through this every election year! I WANT them to be funny. I'm rooting for them to be funny. I want to be torn down cleverly. Who doesn't? That's the point of the Friar's Club roast. I would LOVE to have a Friar's Club roast hosted by Jeffrey Ross, just to see if I could keep from crying. And then they'd make fun of the crying.
But, dammit, this just isn't goddamned funny. And not because I'm offended or anything. It's poorly worded and constructed. The set up is awful and bumbling. And the punchline isn't even that funny - it just sounds like a lede to a Newsweek article about Obama's move to the center for the general election. It doesn't zing, man!
This zings:
"This weekend, Bill Clinton said Hillary should not drop out of the presidential race. Yeah, when asked why, Bill said, 'Because then she'd come home.'" --Conan O'Brien
Pow! Zoom! To the moon, Alice! See, Bill Clinton has a wandering dick! And his wife is a pain in the neck! There you have the convergence of two massively overblown stereotypes that actually work for comedy.
The conservative bloggers have suggestions (talk about how he's arrogant! and dorky! and stupid!) but none of them really work because you have to have a predisposition of hating him to find any truth in it. Like, people who hate Obama see arrogance, but people who support him see confidence. It's in the eye of the beholder. But when President Bush says "Put food on your family" nobody can really spin it. They guy sounds like a dumb ass.
Anyway, nobody's going with them on the Obama=dork thing because he usually doesn't look like a dork (he did in a bike helmet, but everybody looks stupid in a bike helmet. Brando in "Streetcar" would've looked stupid in a bike helmet.) And he may have "gaffed" a few times, but nobody's buying that he's stupid. They're swimming desperately against the tide.
Right Wing News is a perfect example. A writer angrily denounces the article thusly:
Obama is pacifistic, green, dumb as a box of rocks, has terrible judgment, is incredibly pompous, regularly tosses people who displease him under the bus, and flip-flops on his positions depending on who's talking to while simultaneously leading millions of liberal zombies around by the nose just by talking about "change" and "hope."
So, to review why none of this works for comedy:
Obama is pacifistic (3/4 of this country hate the war, so they don't find this mockable)
green (Dan Quayle-type jokes don't work because most people don't think he's dumb)
dumb as a box of rocks (see above)
has terrible judgment (see above)
is incredibly pompous (if you hate him, sure)
regularly tosses people who displease him under the bus (so does everyone in politics - not particular to Obama)
and flip-flops on his positions depending on who's talking to while simultaneously leading millions of liberal zombies around by the nose just by talking about "change" and "hope." (yeah - Letterman is gonna kill with all those jokes about how most of the people in his audience are brain-dead zombies. "You're all a bunch of slaves!" And nobody thinks flip-flop jokes are funny. Not "Bush is dumb and Clinton has a ding-dong" funny, anyway)
Basically, Right-wingers are mad that comedy writers aren't following the narrative they're setting out. Like, after eight years of Bush nobody is going to buy that Obama's dumb. You might as well try making comedy about how ugly he is while you're at it.

"Barack Obama is soooo ugly..."
"Actually, he's quite young and attractive."
"No no. You're supposed to say, 'How ugly is he?'"
"Why? I mean, his ears are a little big, but compared to the other trolls on Capital Hill he's goddamned Johnny Depp."
"Fine, I'll finish for you. 'How ugly is he?' He's so ugly his momma had to put a porkchop around his neck to make the family dog play with him!"
"That joke doesn't make sense when its about someone who's attractive."
"Liberal zombie!"
As the article points out, for the comedy to work for a broader audience you have to latch onto something that is essentially true. It's the difference between a joke that works for Jay Leno and a joke that works for a group of republicans sitting around drinking, or circle jerking on a political blog. And I'm not disputing that Obama has changed positions on important issues or that he's made some bone-headed mistakes. I'm saying that you'd have to be a political wonk to know that stuff and find the jokes funny. Like, late-night jokes about Hillary had nothing to do with her immigration policy or whatever: they mostly were about her ruthless ambition. You don't need to read the New York Times every day to get that impression of her.
Case in point: Right Wing News's repurposed Barack Obama campaign posters. It's a tool that lets you make your own ___________ We Can Believe In poster. They make three: "Flip Flops We Can Believe In", "A Messiah We Can Believe In" and "A Jimmy Carter We Can Believe In".
The first one is meh (only wonks like flip-flop jokes and the tag probably won't stick). The second one makes fun of his voters and not really him (though it is the funniest, especially with the background image). And nobody give a crap about the Jimmy Carter thing (especially since, as of a year ago, Jimmy Carter had about a 70% favorable rating. It's not an insult to compare Obama to someone people like.)
So there you have it. I consider this a comedy space race with The Other Side. We will put this comedy man on the moon before the Russians. We will find a way to make fun of Barack Obama and we will declare victory at the polls AND in our crummy late-night monologues. That's how soundly the Republicans will be defeated this year. Liberals will fix their war, fix their economy, fix their faces, and be the first ones to pounce when Obama steps on a rake or something. To the ready.

