Barack Obama’s Top Secret Plan to Make You Laugh

Nobody—outside a small group inside the White House—knows for sure what President Obama will say when he speaks at the White House Correspondents' Dinner on Saturday. In the half-century in which presidents have tried out their comedy chops at this dinner, there have been fewer leaks than just about any presidential address. In fact, there is only one known instance of a joke leaking in advance. That was in 1998, when CNN's John King got ahold of one of President Bill Clinton's jokes, triggering an emergency meeting at the White House and an internal debate on whether to drop it from the text.

Speechwriter Michael Waldman called it "the unthinkable" and "the latest skirmish in the war with the press." In his book POTUS Speaks, Waldman wrote, "Most leaks were shrugged off. But leaking a joke—well, this had never happened. It demanded a witch hunt." He recalled that "angry staff members gathered" prior to the dinner. Mark Katz, an outside writer often brought in by Clinton to make these dinner speeches funnier, also witnessed the fury at the White House over the leak. He recalled Waldman's reaction. "The gravity of his tone and demeanor might have scared me into thinking there was some kind of national emergency underway," wrote Katz in his book Clinton and Me.

After a heated discussion in the Map Room, it was decided to keep the leaked joke in the speech—but change the punch line to punish the leaker and send a message to King. Either that message was received, or no news organization has considered jokes to be newsworthy enough. Whatever the reason, no presidential joke has leaked before any of the 17 Correspondents' Dinners since.

(The joke itself, which one of the writers conceded was "unfunny," had Clinton speculating about which member of Congress would follow John Glenn into space. It allowed the president to jab at his biggest tormenter in the House, concluding, "Godspeed, Dan Burton." The punch line changed to "Godspeed, Dick Armey," and life went on.)

Yet since this is Obama's seventh time at this dinner, we have a pretty good idea what to expect. You don't really need a leak to tell you his go-to moves, favorite joke targets, and most reliable punching bags. You only have to go through the numbers.

They tell you that he's likely to speak for just around 19 minutes—his shortest was 16 minutes in 2009; his longest, 22 minutes in 2013. His preferred path to a laugh takes him, every year, to Kenya, with 12 jokes about the controversy over his place of birth. The second-biggest butt of his jokes is Fox News at eight jokes, followed by Vice President Joe Biden at seven and Hillary Clinton at five.

Other go-to topics for easy humor are NBC/MSNBC (four times), as well as his TelePrompTer, his daughters, his bad polls, CNN, and Mitt Romney (each three times). Sometimes, he likes to combine topics as he did in 2013, when he merged talk of his past with concern about his graying hair to lamen: "I'm not the strapping young Muslim socialist that I used to be."

Of course, as Obama's disclosure Thursday of the terrorism strike gone bad reminds everyone, a great unknown of any such social gathering is when world events make humor inappropriate. Ronald Reagan said he "just didn't feel" like being funny in 1983 on what he called the saddest day of his presidency when he came to the dinner after viewing the flag-draped coffins of Americans returning from Beirut. And George W. Bush at the 2007 dinner, only five days after 32 people were killed at Virginia Tech, declared, "I decided not to be funny."

Sometimes, it's been a close call. Clinton considered dumping his jokes in 1994 when Richard Nixon died the day before the dinner. He settled instead on a moment of silence.

Naturally, some of Obama's most memorable jabs were aimed at Republicans. In 2009, he described then-House Minority Leader John Boehner as "a person of color," quickly adding that it was "not a color that appears in the natural world." In 2014, he doubled down, noting that House Republicans were giving Boehner, by then the speaker, "a harder time than they give me—which means orange really is the new black." And Senate Republican leader Mitch McConnell was not spared. In 2013, the president sarcastically noted that many were urging him to have a drink with McConnell. "Really?" he said to growing laughter. "Why don't you get a drink with Mitch McConnell?"

The president also has some topics that obviously tickle his fancy because he looks for openings to make jokes on them. There were those two jokes about eating dogs when he was a boy. And he couldn't hide his delight in making jokes using rap terms or African American slang about former Republican National Chairman Michael Steele.

Of course, it's not hard for the president to get a laugh—from himself. He is his own best audience. He just can't help himself. He has laughed at his own jokes 53 times in those six speeches, according to a National Journal review. Sometimes he just cracks himself up—including the Michael Steele jokes. After calling Steele "Notorious GOP" in 2010, he laughed and confessed, "I did a similar routine last year. But it always works."

What also always works for him are the props, the fake photos, the faux videos, and the sight gags. There were those rising TelePrompTer screens in 2009, the two ferns in 2014, and, memorably, the off-stage sound of him flushing a toilet in 2012 as a supposedly concerned press secretary Jay Carney begged "someone back there please turn off the president's mic."

There have been 30 doctored photos showing everything from his White House throne, the devil with Sen. Ted Cruz, and Biden throwing a shoe at Hillary Clinton, to an Oval Office meeting with a pirate, fake Politico headlines, the graying of his hair and an experiment with Michelle-inspired bangs. And there have been seven videos—ranging from a polished and clever Steven Spielberg-narrated look at Obama playing actor Daniel Day Lewis playing Obama, to a Lion Kingvideo of Obama's African birth, to a demonstration of how Mitt Romney and Obama treat dogs.

Most of the president's jabs are playful, at most making the target squirm amid the laughter. But occasionally they have drawn blood—and none more so than in 2011.

That dinner is best remembered for the president sitting on the secret that he had just ordered the mission to kill Osama bin Laden. But it was also when he launched the most protracted and withering assault seen at any dinner in memory. The target that year was Donald Trump, a man who craves the spotlight and at the time of the dinner was basking in it with his hints that he would run for president, and his increasingly wild accusations about the president's place of birth. But Trump didn't seem to relish the spotlight this night, as the cameras found him at Table 96 right in the middle of the ballroom, guest of The Washington Post.

The president's 200-word barrage eviscerated Trump, concluding in a faked-up photo of how Trump would turn the White House into the "Trump White House Resort and Casino." The snippet before that photo may turn out to be the most-remembered attack of the Obama era dinners:

Donald Trump is here tonight! Now, I know that he's taken some flak lately. 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? But all kidding aside, obviously, we all know about your credentials and breadth of experience, um. For example—no seriously, just recently, in an episode of Celebrity Apprentice at the steakhouse, the men's cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so, ultimately, you didn't blame Lil Jon or Meat Loaf. You fired Gary Busey. And these are the kind of decisions that would keep me up at night. Well handled, sir! Well handled.

On Saturday, Trump is scheduled to return to the dinner once again, this time as a guest of Fox News. With no leaks of any jokes, there's no way to know if, once again, he'll be a presidential target. Can Obama resist when Trump just this week insisted that he is "totally serious" about running for president?