A Guy Walks Into an Oval Office

How political speechwriters do comedy.

Was Obama funny or vicious at the White House Correspondents Dinner? The Washington Post sizes up the president’s jokes.

When politicians tell jokes, some kill. Others kill their chances of ever becoming president.

Perhaps the greatest flop in recent memory was a speech given by then-House Minority Leader Dick Gephardt in 1995 at the annual dinner hosted by the Gridiron Club in Washington. Gephardt came out wearing a Boy Scout uniform—he was an Eagle Scout—and pledged to “clean up the image of Congress.” The response: silence. “Nobody got it,” remembers Eli Attie, who was then a speechwriter for Gephardt. “Then he was just standing there in a Boy Scout uniform for the rest of the speech … and you’re looking at his pale, overexposed kneecaps. Which was funny on one level, but not the level we wanted.”

The written jokes bombed, too. The next day’s Washington Post described the performance as “rife with wooden, slightly nasty attacks on Republicans” that “raised more eyebrows than smiles.” “Dick’s just not funny—everybody knows that,” Gephardt’s wife was quoted saying. “I enjoyed your remarks, Dick,” Bill Clinton said at the dinner. “But you and I are in the minority.”

Gephardt’s speech broke all the rules of political joke-making—rules that Barack Obama and his team of joke writers would be wise to follow in Saturday’s speech at the White House Correspondents Dinner.

First, the obvious: Be self-deprecating. “Humor is a powerful weapon,” says Jeff Nussbaum, a speechwriter who has worked for Al Gore and Joe Biden. “But to earn the right to wield it against others, you need to turn it against yourself first.” Gephardt made the mistake of going after Republicans without first winning over the audience. “There wasn’t that same goodwill,” recalls Attie. “He was a little too harsh on people.”

Barack Obama grasps this. His 2009 speech was peppered with teleprompter jokes (“Pause for laughter,” he said out loud), a bailout quip (“Car and Driver named me auto executive of the year”), and predictions about his second 100 days (“I will consider losing my cool”). Which then allowed him to mock everyone around him. He noted that Michael Steele was “in the heezy.” He previewed Dick Cheney’s memoirs, How to Shoot Friends and Interrogate People. He called John Boehner a “person of color.” The whole time, Obama seemed to be half-chuckling to himself. “That gave him little sense of ironic distance,” remembers Attie. “Like, Here is this exercise we assemble here to do.”

The second rule (and the motto of the Gridiron Club itself): Singe, don’t burn. The best jokes walk right up to the line—but don’t cross it. “You never want get an oooo out of the audience,” says Jeff Shesol, a former deputy speechwriter for Bill Clinton. “I can’t believe you just said that is pretty good, but oooo is different.” Gentle ribbing is good. At last year’s WHCD, Obama welcomed his audience of journalists. “Most of you covered me,” he said. “All of you voted for me.” (This year, jokes about the media’s love affair with Obama aren’t as relevant.) Some speeches do push the limits of decorum. Someone who attended this year’s off-the-record Alfalfa dinner recalls a senator telling a joke about Peter Orszag, the OMB director whose girlfriend gave birth in 2009: “Peter Orszag proved himself adept at juggling the country’s finances,” the joke went. “In the end, he managed the bailout, but he didn’t manage the pullout.” The crowd loved it. “You could actually see the house coming down, chunks of plaster landing in the lobster bisque,” recalls the attendee.

Burns do occur. Lines get crossed. In 2004, New Jersey Gov. Jon Corzine hired Nussbaum to write some jokes for a speech at a Washington Press Club Foundation dinner. Nussbaum sent him a few ideas, including this one: “Sharing a media market with Chuck Schumer is like sharing a banana with a monkey. Take a little bite of it, and he will throw his own feces at you.” Nussbaum didn’t expect Corzine to use it, he says. But Corzine did. Schumer demanded an apology. “It soured the relationship between the two of them,” Nussbaum says.“You forget that something that was funny in a small room isn’t funny in a big room.”

The most notorious line-crossers are the hired entertainment. Stephen Colbert’s send-up of President Bush and Washington journalism at the WHCD in 2006 got a chilly response from the audience, including the president himself. But it was nothing compared to the backlash against Don Imus when he hosted the White House Radio and TV Correspondents Dinner in 1996. “He told one blowjob joke after another, standing ten feet from the president and nine-and-a-half feet from the first lady,” recalls Christopher Buckley, who wrote speeches for George H.W. Bush. “It was excruciating.” Perhaps that’s better than the alternative: Ben Stein’s address to the Radio and TV dinner in 2001, which included an assassination joke on the eve of the 20th anniversary of the shooting of Ronald Reagan in the hotel where it happened, redefined unfunny. “The audience simply stopped listening to him about half way through,” recalls Buckley.

Which brings us to the third rule: Use jokes as damage control. Clinton never made light of the Lewinsky scandal directly. But in 1999, he started off his WHCD speech by somberly noting that had the Senate’s impeachment vote gone another way, he wouldn’t be standing here today. Pause. “I demand a recount.” The quip not only defused the tension surrounding the Lewinsky affair. It also captured Clinton’s messy relationship with the press.

The damage control strategy can backfire. Al Gore often joked about his stiffness—”Al Gore is so stiff, racks buy their suits off him;” “Al Gore is so boring, his Secret Service code name is Al Gore”—until his speechwriters realized they were only reinforcing the image. A joke exploded in the face of George W. Bush when he cut a video for the 2004 Radio and TV dinner. In it, he was shown peering under furniture in the Oval Office. “Those weapons of mass destruction have got to be here somewhere,” he quipped. People laughed, but by Monday the press had decided it was in poor taste.

And of course there’s Rule No. 4: Delivery matters. John Kerry learned this the hard way in 2006, when he botched a joke in front of a group of students. He meant to say that if you don’t study hard, you’ll end up making dumb decisions like President Bush’s decision to invade Iraq. Instead, he said that students who don’t perform well would get “stuck in Iraq.”

The best political comedy speeches are a mix of punchlines, extended riffs, and set pieces. Punchlines are relatively easy. White House speechwriters usually solicit ideas from funny people around the West Wing—apparently David Axelrod is a comedic force—as well as TV writers and professional comedians. Clinton and Gore, for example, relied heavily on Al Franken and Jay Leno. Other times they’ll simply pay an outside writer to do it.

The initial “joke dump” then gets whittled down to the gems, which one or two speechwriters craft into a speech. They also try to come up with a few riffs—see Obama’s series of jokes about his second 100 days—that play to the politician’s personality. The strongest gags, however, are often the set pieces. When Gore headlined the Gridiron in the ‘90s, he had recently told FBI investigators that he had not been part of certain controversial fundraising discussions because he’d had a lot of iced tea to drink and had taken many bathroom breaks. So he began his speech by chugging a tall glass of iced tea, hiking his pants, and saying, “I can’t stay long.”

Writing jokes for politicians is different from writing for a late-night talk show. (Although sometimes the two overlap.) “For a politician, it’s not just about getting laughs,” says Eric Schnure, a speechwriter who has written for both Democrats and Republicans. “It’s about being liked.” Some humor is therefore off limits. No impersonations. No joking about loss of life. No cursing. It’s just not worth offending someone you have to work with the next day.

The best jokes often make a point. In his book The Political Speechwriter’s Companion, Robert Lehrman highlights one story politicians love to tell about the man who orders rabbit stew at a restaurant and “complains to the manager that it tastes like horse meat. The manager confesses he did put some horse meat in the stew. ‘How much?’ ‘It’s equally divided. One horse, one rabbit.’ ” It’s funny, but it also makes a point about the unevenness of political compromise.

Luckily for speechwriters, the bar isn’t that high. Even the lamest jokes get laughs. “The weird thing about all these jokes is, none of them are funny,” says one Senate speechwriter. It’s more about seeing normally stentorian politicians crack wise. The mere fact of it is entertaining. As Attie puts it: “It’s humor in a suit.”

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