White House correspondents dinner: Barack Obama has one mean wit

Updated 10:54 PM EDT, Sat April 25, 2015
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Here’s some advice: If you’ve crossed Barack Obama in the last year, you might want to stay home on Saturday night.

The President is sharpening his sword ahead of the annual White House Correspondents’ Dinner, and past targets like Donald Trump, John Boehner and Mitch McConnell know how deep Obama’s words can cut.

READ: What to expect in Obama’s speech Saturday night

Of all recent presidents, Obama has taken humor closer to the hard-to-define threshold of what is appropriate coming from the mouth of a president.

Sure, like his predecessors he usually opens with the regular ribbing of the press and his staff and greases the way for his biting attacks with self-mockery, poking fun, for example, at his penchant for teleprompters or his allergy to D.C. backslapping.

But Obama’s jokes can also be daring and cut deep. With adept comic timing, the president – whose political enemies have often put his image through the shredder – leads his audience right up to the line … and sometimes over it.

In his most merciless routines, Obama has compared Republican House Speaker Boehner’s permanent tan to his own skin tone, which according to Obama proves “orange is the new black.”

“He’s a person of color, but not a color that appears in the natural world,” Obama once said of his House of Representatives nemesis.

McConnell, the Senate majority leader, has also gotten it in the neck. To pundits who said he should spend time with the Republican Senate bull, Obama responded archly in 2013: “Why don’t YOU get a drink with Mitch McConnell.”

Obama’s not just playing for laughs. There’s something deeper going on. For a president who rarely loses his temper in public, the dinner offers a safety valve.

“It is a safer environment to take on some of those more hot-button issues and deflate them,” said Adam Frankel, a speechwriter for Obama during his first term. “In the course of everyday speechwriting, there are opportunities to deliver lines here and there, but not opportunities for extended riffs and humor of this kind.”

Obama for years peppered campaign speeches with jokes about the birther movement’s claims that he’s not a natural-born American and therefore not qualified to serve as president. But it wasn’t until the 2011 White House Correspondents’ Dinner that the president was able to expose the absurdity of the attacks. And that was bad news for the Donald, whom he eviscerated over the issue.

Breaking taboos

Obama, the pathbreaking first African-American president, has been able to take the speech further than it has ever gone before, even broaching the taboo topic of race in ridiculing GOP efforts to court minorities by saying former party chairman Michael Steele, who is black, was in the “heezy” – urban slang for house.

Obama gets away with dropping the anvil like this because he often delivers his jokes with a wink and a wide smile, bringing the audience along with a conspiratorial chuckle as he scans a punch line before saying it out loud.

But aides said that he is careful to chose his targets, viewing political opponents and the powerful as fair game.

“He doesn’t want to be nasty. He doesn’t want to hurt anybody personally,” said a senior Obama administration official, speaking on the condition of anonymity to discuss the president’s views of the speech.

“So much of the conversation in Washington caters to the extreme – either the trivial or the hyperbolic – and humor is a good way to poke holes in both,” said the administration official. “There are things he wouldn’t say in a press conference, for example, because they would come across as whiny or self-aggrandizing, but he can say them through humor at the dinner.”

The dinner is a rare chance for presidents to get a free pass to ridicule and swat at political enemies, offering them an informal setting to say things they have long wished to but would be too impolitic in a formal White House setting.

“Humor is both a shield and a sword in politics,” said Ari Fleischer, who served as former President George W. Bush’s first press secretary. “Humor is a shield because if people like you they will tend to give you the benefit of the doubt. It is a sword because one of the most effective ways to make fun of your opposition is humor as opposed to direct, frontal, mean-spirited attacks.”

Even so, some Republicans balk at Obama’s caustic style, which comports with their view that the president has elevated partisanship to new levels.

And when Obama hits his stride, it’s not always comfortable in the cavernous Washington Hilton ballroom. Like the best comedians, his most barbed lines often trigger a second of shock before the laughs.

But it’s not just Obama’s personal style that has made the annual event rawer; so have the times.

“The White House Correspondents’ Dinner is edgier than it used to be,” said Robert Lehrman, once a speechwriter for former Vice President Al Gore, who has written a manual for political speechwriters.

“I think everything else has gotten more hostile in politics now. Especially on the Hill. So why not jokes?”

Satire is king

Obama’s is a brand of humor to match a polarized age where the stand-up gags of late-night hosts on broadcast TV seem tame compared to the satirical swipes of Comedy Central – and when a veneer of good humored bipartisanship has long since been torn away.

Former President Ronald Reagan once lobbed gentle one-liners at the White House Correspondents’ Dinner like he was joshing show-biz pals at a roast or warming up the audience at the “The Tonight Show.”

Three decades later, Obama’s humor is more cruel, more personal and inherently more political.

More Jon Stewart than Johnny Carson.

Jeff Shesol, a speechwriter who prepped Bill Clinton for the big night when he was in the White House, said presidents must show they are comfortable with power but can also laugh at themselves.

“This isn’t just light entertainment. It’s a high-wire act for the president, and more so in the last decade or so than it used to be. We live in a different era,” Shesol said.

Politicians are frequent targets, but not the only ones. Obama likes to jab the media as well, throwing daggers at Fox News for perceived bias, cable outlets that he says prize trivia and insider publications like Politico that he accuses of hyping gossip.

“Some of you covered me. All of you voted for me,” Obama told the press in a poke at perceived liberal media bias at the dinner in 2009.

In an uproarious moment in 2011, Obama said he had unearthed a video of his birth – before playing a scene from “The Lion King,” where the infant cub that will be king is revealed to the world in a ray of light atop an African mountain.

The joke was funny because of the element of surprise and the clashing contexts of Obama’s biography and the movie. But the president was also mocking his own persona as a semi-divine figure chosen to lead his people out of darkness.