There's more than just idle curiosity in asking this question. With the White House Correspondent's Dinner coming up on Saturday night, President Obama is expected to mouint the platform and perform for about 20 minutes, reeling off a series of one liners directed at his enemies - and, more importantly, himself.

Except Obama apparently doesn't do self depcrecating humor well, according to this Todd Purdum article in Politico.

President Barack Obama is very smart (as he could tell you). He is also very funny (and the first to laugh at his own jokes). He is a master of comic timing, has an appealing sense of the absurdities of his chosen profession and an unerring ear for the withering one-liner.

As long as the subject is someone else.

When it comes to the sine qua non of political humor — devastating self-deprecation — Obama is less skilled or at least less willing to play an A game, as this weekend’s White House Correspondents’ Dinner is once again likely to show.

Sure, Obama makes fun of himself: for his big ears, his graying hair, his sagging approval ratings, even his bad bowling (though he stepped on a joke about the last subject with Jay Leno in 2009 by adding an ill-considered ad lib about his Special Olympics-level skill, for which he was forced to apologize). And the president has proved himself a good sport, enduring Zach Galifianakis’ absurdist insults on “Between Two Ferns,” where he went to promote his health care plan.

But Obama is much more likely to reserve his sharpest flashes of wit for his adversaries, antagonists and even (in a kind of throwback Henny Youngmanesque style) for the wife he invariably portrays as hectoring.

And as is often the case with other rhetorical aspects of his presidency, Obama sometimes seems to deliver his jokes — however effective they may be — with the disembodied distance of someone observing his own performance.

“Here’s my take on President Obama,” said Mark Katz, a veteran Democratic humor writer. “I think he’s smart, he’s funny, he’s self-aware. To me, it doesn’t sound like his voice. To me, he looks like a guy having a great time reading the really funny jokes his staff put together, but I just don’t hear his voice. I just don’t.”

Obama generally eschews the kind of deadly self-directed stinger George W. Bush delivered at his first Gridiron Club dinner in 2001, when he allowed: “Those stories about my intellectual capacity do get under my skin. You know for a while I even thought my staff believed it. There on my schedule first thing every morning it said, ‘Intelligence Briefing.’” And near the end of his tenure, Bush said he was considering “something really fun and creative” for his memoirs, “You know, maybe a pop-up book.”

Clearly, Obama is no Ronald Reagan, whose self-deprecating humor could disarm his most contentious opponents. In fact, Obama's humor can become quite mean spirited - more mocking than funny:

Obama’s former chief speechwriter, Jon Favreau, insisted that this president “very much understands that you don’t get very far purely by destroying the other side.”

Yet when asked for examples of Obama’s best self-deprecating lines, Favreau struggled a bit for an answer, eventually citing jokes about big ears and bad poll numbers. “In the early years,” Favreau added, “he joked about the image of him as a Messiah, and he joked about his birth certificate.” (At the Al Smith Memorial Dinner in New York in 2008, Obama declared, “Contrary to the rumors you’ve heard, I was not born in a manger. I was actually born on Krypton …”)

But those jokes are in fact about others — Obama’s most fervent, starry-eyed supporters, or the virulent “birthers” who questioned his American citizenship — and not really about himself. The most lethal example of Obama’s ripostes to such critics came at the White House Correspondents’ Dinner in 2011, with his extended riff on Donald Trump, who was in the room and decidedly not amused.

“Now, I know he’s taken some flak lately,” Obama said of the man who had waged a vigorous media campaign questioning the president’s citizenship, “but no one is happier, no one is prouder to put this birth certificate matter to rest than the Donald. And that’s because he can finally get back to focusing on the issues that matter — like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”

Humor and politics have always been a tense combination. Laugh it up too much and people don't think you're serious enough. Not enough humor will make people think you're boring and too staid to serve. It's a delicate balance that only the exceptional politicians can manage.

Can you imagine Obama saying something like this?

At the 1987 Gridiron, Reagan famously mocked his reputation for laziness and inattention by solemnly saying, “It’s true that hard work never killed anybody, but I figure, why take the chance?”

John Kennedy was another president who knew how to make fun of himself.

John F. Kennedy retired the self-deprecation title more than half a century ago, when he was gearing up to run for president in 1958. At that year’s Gridiron dinner, he forever inoculated himself from charges that he was coasting to election on his family fortune, reading a mock telegram from his father: “Dear Jack: Don’t buy a single vote more than is necessary. I’ll be damned if I’m going to pay for a landslide.”

How about Reagan's disarming joke in the 1984 debate with Walter Mondale?

Some observers believed that Reagan won re-election at that moment.

It's not that Obama isn't as good as Reagan at telling jokes. That's an unfair comparison given that Reagan was a trained actor and had been delivering one liners at dinners and events for 30 years.

Obama's problem is that he doesn't get the essence of political humor - how it should illustrate larger points or inoculate the president from some criticism. Obama's sneering, sarcastic humor that diminishes his opponents rather than elevating himself has only his sycophants laughing while his opponents stew.

Keep that in mind if you watch the WHCA dinner this weekend.