The recent New Yorker magazine cover depicting Barack Obama as a Muslim and Michelle Obama as a gun-toting, Angela Davis style radical, makes one thing perfectly clear: As easy as it sometimes looks, creating a good political cartoon is a very difficult thing to do. The New Yorker cartoon fails badly, not because it is offensive, but because its satirical message is so unclear that it leaves the reader confused rather than amused. The cartoon is "too hip for the room," confronting us, jarring us, without conveying any clear-cut satire or humor. As such, the cartoon falls flat. The mere fact that the New Yorker editors were forced to run around all day trying to explain the cover, reveals how flawed the cartoon was.

As novelist-essayist Arthur Koestler pointed out years ago, all good humor works simultaneously on two levels, as two seemingly incompatible frames of reference collide to produce the explosive result that we call "humor." It could be as primitive as a dignified person slipping on a banana peel, that is, the high and mighty being brought down to size. Or it could be the woman, worried that her son is seeing a psychiatrist, who is reassured by a friend, "Don't worry, it will all work out as long as he is a good boy who loves his mother." When the psychiatric meaning and the everyday meaning of loving one's mother collide, we get irony and humor.

The problem with the New Yorker cartoon is that there is no second frame of reference to help us. We see the image and wonder, is the creator criticizing Obama? Is he sympathizing? Is he commenting on shameful rumor-mongering? With so little context provided on the cover, we are at a loss as to how to respond, and that is not funny. Indeed, when CNN did a man-on-the-street poll about the cartoon, virtually no one saw it as a hip, ironic statement on viral rumor-mongering during the campaign. Rather, they tended to see it as merely an insulting depiction of Obama. That's not funny.

However, the cover could have been funny: Pulitzer prize winning cartoonist Nick Anderson, the current president of the American Association of Editorial Cartoonists comments, "“I think, as a piece of satire, it utterly fails." Anderson goes on to say that a caption such as "The Politics of Fear," would have added some context and clarity to the image. He continues:

It would have been even stronger had they shown an enemy of Obama painting the picture, or imagining it in their head.

Personally, I would have tweaked the cartoon by showing two images, a wholesome image of Obama and family, juxtaposed with an imaginary voter's hostile "email" version of Obama. This would have provided context and humor.

Contrast the failed New Yorker cartoon with one by cartoonist Matt Wuerker of politico.com that covers similar subject matter. Wuerker's cartoon depicts four blue collar white males sitting in a bar watching Obama on an overhead television set:

The first one says: Ya know he's a Muslim.

The second one says: And refuses to say the Pledge!

The third one says: And took his oath on a Quran!

The fourth one says: And what's worse, he's an elitist who thinks we're gullible ignoramuses!

Now that's funny! The image of four blue collar whites buying into every scurrilous rumor about Obama, then claiming that they get no respect, is a sad, painful and hilarious commentary on one of the important dynamics of this campaign. As such, it speaks more eloquently about Obama's difficulties with working class voters than virtually all of the so-called communications experts I have listened to on this subject. It is easy for such experts to bring out the cliche that Obama "can't relate" to these voters, or that he "can't close the deal." The fact is, Obama is great with working class indidviduals; he was highly successful organizin g low income individuals on the South Side of Chicago. The deeper truth here is that Obama's problem with working class whites has less to do with him than with them; even the strongest message can be undermined by suspicion and racism. The New Yorker magazine was making a laudable attempt to address this issue, but failed.

On a related note, sometimes timing and circumstance determine whether something is funny or not. On Sunday, when CNN anchor Wolf Blitzer asked the Republican South Carolina Governor Mark Sanford if there were any differences between the economic policies of George W. Bush and those of John McCain, here was Sanford's response:

Um, yeah. I mean for instance, take, you know, um, uh, take for instance the issue of, uh, of, um (drums fingers), I'm drawing a blank, and, I hate it when I do that, particularly on television....

If you saw this exchange live, it was excruciatingly painful to watch. Blitzer himself said afterward, "It was painful for me, and I was the questioner!" However, imagine a Democratic campaign ad in September, in which an ominous voiceover says, "Can you name any differences between the Bush economic plan and that of John McCain?" Cut immediately to Mark Sanford hemming and hawing without being able to answer. The voiceover then says, "Don't worry Governor Sanford, we can't think of any differences either!& quot; I can assure you, in this context, Mark Sanford will be hilarious! And I have to assume that the Obama staff is preparing such an ad even as I write this. And as for Sanford? You can bet that McCain scratched him off the veep list so fast it aint funny.