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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.”

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