During his five decades in comedy, impressionist Rich Little has performed in glitzy Las Vegas casinos and backwater Canadian nightclubs, on television and in films, before intoxicated hecklers and dignified heads of state.
For sheer degree of difficulty, he said, one venue stands out.
"The White House [Correspondents' Association] dinner is probably the hardest show I've done in my entire career," said Mr. Little, 73, who headlined the event in 1985 and 2007. "Absolutely. You have to be political and take a few jabs. But you can't be too strong. And if you don't come on strong, they say you're doing your Vegas act. It's kind of a no-win situation."
Mr. Little paused — only not to deliver a punch line.
"Every time I hear who is going to be on, I think, 'Good luck,'" he said. "I hope they know what they're getting into."
This year's human sacrifice is late night talk show host Jimmy Kimmel, who headlines the 2012 White House Correspondents' Association dinner at the Washington Hilton on Saturday night.
Crack a few jokes. Mingle with Hollywood (George Clooney, Uggie the dog) and the Washington power elite (reporters, congressmen, military brass, assorted undersecretaries of something or other). Shake hands with the president.
In theory, the star-studded annual dinner is a plum gig, a once-in-a-lifetime chance for comics to enhance their national profiles and gag writers to put material in the mouth of the world's most powerful person.
In reality, it's a nerve-wracking, sweat-through-your-tuxedo pressure cooker for comics and presidential joke penners alike. Off-color and ill-advised jokes can result in national controversy; political cracks can touch off outraged partisan food fights.
Infamous case in point? In 2006, Stephen Colbert delivered a withering roast of President George W. Bush — offending the administration's backers, delighting its detractors and touching off a media firestorm … all because Mr. Colbert essentially stayed in character, offering the same satirical send-up of a cocksure, un-self-aware conservative talk show host that he does on television.
"When they booked Colbert, I'm not sure they really understood what he was going to do," said Mike Larsen, who has written for HBO's "Real Time" and once worked for Rep. Jackie Speier, California Democrat. "I don't think people in the room knew where he was joking and where he wasn't. And he went pretty far.
"But that's Washington. The politicians from both parties all want to appear hip, have some cutting edge performer, and then being politicians, distance themselves from every joke that wouldn't even raise an eyebrow at a late night comedy club. They want the rock concert T-shirt, but don't want to have to stand near the speakers."
From afterthought to tightrope
First held in 1920, the correspondents' dinner has morphed from a largely unremarkable, inside-the-Beltway evening of politicians and the media letting their collective hair down over a few yuks — and a few too many drinks — into a full-fledged celebrity circus-cum-presidential comic rite of passage.
In 1975, for example, President Ford lampooned his clumsy image by spilling tableware into the lap of comedian Chevy Chase, a clever inversion of Mr. Chase's famous portrayal of Mr. Ford as a klutz. And that was enough. At least at the time.
Today, Washington's "nerd prom" is broadcast live on cable television and covered like an ersatz Oscars. Presidents aren't simply expected to laugh; they're expected to deliver material that, well, kills. (Not literally, of course — although President Obama came close in 2010 with his warning to the Jonas Brothers: "Sasha and Malia are huge fans. But boys, don't get any ideas. I have two words for you: 'predator drones.'")
As the event has evolved, its humor has become professionalized, with the correspondents' association booking major performers such as Craig Ferguson and Wanda Sykes and Mr. Obama tapping "Daily Show" writer Kevin Bleyer to pen some of his 2010 material.
"The dinner is taken much more seriously in this town than it used to be," said longtime speechwriter and humorist Landon Parvin, who penned material for President Reagan and for Mr. Bush. "They televise it. There's a bigger audience. The expectations are higher.
"It used to be that if you goofed, it didn't make much difference. There's more pressure now — both to be funny but also to hit the mark exactly."
And therein lies the problem, for comics, writers and presidents alike. Humor involves risk. It involves straddling — and sometimes crossing — the lines of social decorum and good taste.
Politics, by contrast, involves running like heck from the first whiff of danger. Washington is a bureaucratic, risk-averse town; the Washington Hilton's International Ballroom is a far cry from the typical comedy club, less a speakeasy than a humor tightrope.
Three years ago, Miss Sykes, an oft-edgy comedian, performed at the dinner, joking that "I think maybe Rush Limbaugh was the 20th hijacker [on 9/11], but he was just so strung out on OxyContin he missed his flight."
Miss Sykes also said that she hoped the conservative talk show host's "kidneys fail."
The quips — referencing Mr. Limbaugh's painkiller addiction and stated desire to see Mr. Obama's administration fail — were roundly panned for being mean-spirited.
On a subsequent broadcast of CBS' "Early Show," co-host Harry Smith recalled a post-dinner conversation with liberal television host Keith Olbermann that encapsulated the evening's comic dilemma.
"The whole place groaned [at Miss Sykes' joke]," Mr. Smith said. "And I ran into Keith Olbermann afterwards … he said, 'I'm not sure, I think that was probably — probably in bad taste.' I said, 'What do you think her job is?'"
Rules of the comic road
Mark Katz can relate. A former creative consultant to the Democratic National Committee, he helped pen gags for President Clinton's correspondents' dinner appearances, working in what administration insiders playfully dubbed their "comedy war room." One joke — written in 1998, following the Monica Lewinsky and White House fundraising scandals — never saw the light of day.
"It was, 'Looking back, maybe I should have raised money in the Oval Office and had sex in the Lincoln Bedroom,'" said Mr. Katz. "I knew that was going nowhere. At the White House, people are very blunt about what lines you cannot cross.
"Still, my instincts are to address those topics. You have to. If you can figure out the worst thing your opponent can say about you and find a way to joke about it, you've disarmed them. There's power in that. But there are rules of the road you need to understand."
What, exactly, are the rules? A quick primer:
Do be self-deprecating: Presidents can never go wrong mocking themselves. Or members of their staff. In fact, doing so is pretty much mandatory.
At the 2000 dinner, Mr. Clinton brought down the house with a six-minute farewell video that showed him wandering the empty halls of the White House, making origami ducks and playing Battleship with the chairman of the Joint Chiefs of Staff — all of it spoofing the final, lame duck days of his administration.
In 2009, Mr. Obama made fun of both his own use of teleprompters and his vice president's tendency to veer off script, cracking "in the next hundred days, I will learn to go off the prompter and Joe Biden will learn to stay on the prompter." A few years earlier, Mr. Bush cleverly spoofed his reputation for self-confidence by joking, "I was going to start off tonight by telling some self-deprecating jokes, but then I couldn't think of any mistakes I've made to be self-deprecating about."
"The president is the most powerful person in the world, so the last thing you want to see is him being a bully," Mr. Katz said. "That is why it's so important to mock yourself. Only after you've done that will the audience let you poke fun at others."
Don't be overly partisan: Washington is a city divided, a realm of endless political warfare. Gentle jabs are OK, but dinner attendees are largely looking for a temporary cease-fire.
Mr. Bush and Mr. Reagan both appeared alongside impersonators to well-received comic effect — the humor was in the mimicry, not the politics. By contrast, Seth Meyers last year reportedly ditched a series of planned gags about the 2012 Republican presidential field midroutine after realizing that Mr. Obama wasn't laughing.
"You have to do political humor, but you don't want to upset half the audience and get them against you," said Howard Mortman, communications director at C-SPAN and a joke writer for Washington celebrities. "You need jokes that unify the room.
"We have all of the old performances at C-SPAN. I've gone back and looked at them, and the ones that work best make fun of Washington and the event itself. One year, President Clinton made a joke about the Taliban and the House Republicans. That didn't go over so well."
Don't forget the larger audience: During the 2004 Radio and Television Correspondents' dinner — a close cousin to the White House Correspondents' affair — Mr. Bush narrated a comic slideshow of photographs from inside the White House — one of them depicting the president looking under furniture in the Oval Office.
"Those weapons of mass destruction have got to be somewhere," Mr. Bush said. "Nope, no weapons over there … maybe under here?" The joke prompted subsequent criticism from Democrats and Republican rebuttals, fueling a cable news cycle of partisan charge and countercharge.
"The WMD joke went over very well in the room, got a big laugh," Mr. Parvin said. "We thought we were making fun of ourselves, and no one would ever use a joke if they thought it would be harmful or hurtful in any way.
"But you make mistakes. In retrospect, it was a political mistake and was used for political purposes. That's why these events are not as much fun as they look."
A chance to talk back
Indeed, the dinner's biggest potential humor pitfall is getting sucked into a media-powered, Internet-turbocharged vortex of umbrage taking, a familiar Washington kabuki played for political points. For performers and joke writers, that means watching what they say; for presidents, that means watching what they laugh at, too: When Miss Sykes was criticized for her jokes about Mr. Limbaugh, Mr. Obama took heat for appearing to smirk at them.
With Washington so partisan and uptight, a reasonable observer might ask: Why do humorists even bother?
According to comedian Elayne Boosler, who performed at the 1993 correspondents' dinner, the opportunity is simply too good to pass up.
"Do you know how great it is to get to talk back to Congress?" she said. "To have a go at the self-interested people who ruin your little life? It's a gift. I wish I could do that dinner every night."
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