The best and worst of the White House Correspondents’ Dinner

A young Jon Stewart, a brilliant Stephen Colbert, and more notable performances from WHCDs past

Topics: White House Correspondents' Dinner, White House Correspondents Association, Barack Obama, joel mchale, Stephen Colbert, Jon Stewart, Seth Meyers, Bill Clinton, George W. Bush, Editor's Picks, , ,

The best and worst of the White House Correspondents' DinnerStephen Colbert provides the entertainment as George W. Bush watches during the White House Correspondents' Association Dinner, April 29, 2006. (Credit: Reuters/Hyungwon Kang)

Tonight in the nation’s capital, influential D.C. journalists will join forces with the most powerful members of our government and a smattering of random celebrities to descend upon the Washington Hilton for the 2014 White House Correspondents’ Dinner.

This year’s event marks the centennial of the White House Correspondents’ Association, a group originally founded to protect the independence of the press corps against encroachment by the Wilson administration. That the group is now best known for a yearly pageant designed to provide “the press and the president an evening of friendly appreciation” is either exciting or depressing, depending on whether or not you were invited to the White House Correspondents’ Dinner.

While you might (rightly) lament that this “friendliness” between our executive branch and the Fourth Estate is in large part responsible for some very unpleasant things, the Correspondents’ Dinner has at the very least produced some notable moments over the years.

Scroll through the video slideshow below to revisit the highlights of dinners past, including Obama’s roast of Donald Trump, a routine from pre-”Daily Show” Jon Stewart, and Stephen Colbert’s tour-de-force smackdown of the Bush administration.



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    Stephen Colbert (2006)

    According to WHCA President Steven Thomma, the job of the dinner's comedian is to treat Democrats, Republicans, and the news media alike to "a little good-natured ribbing." In 2006, Stephen Colbert shattered ribcages and fractured funny bones. Remaining in character as a parody of a right-wing pundit, Colbert called an incompetent, criminal administration just that, through only the thinnest patina of irony.

    For example, in summarizing the conservative worldview he and Bush shared, Colbert hit especially hard: "I believe the government that governs best is the government that governs least," he said. "And by these standards, we have set up a fabulous government in Iraq."

    And at the end of his speech, Colbert made time to thank the gathered press: "Over the last five years, you people were so good—over tax cuts, WMD intelligence, the effect of global warming. We Americans didn't want to know, and you had the courtesy not to try to find out."

    They say great comedy disturbs the comfortable and comforts the disturbed, which might explain The New York Times decision to not to comment on Colbert's performance, and the WHCA's booking apolitical impressionist Rich Little for the following year.

    White House

    Barack Obama (2011)

    In 2011, Donald Trump found he could satisfy his unseemly need for attention by loudly and baselessly declaring President Obama hadn't been born in the United States. The drama of locating and verifying the President's birth certificate provided Trump, cable news pundits, and xenophobic tea partiers hours of welcome distraction, until Obama produced his longform birth certificate at the end of April.

    Days later, at WHCD, Obama congratulated Trump on resolving the matter, and wished him luck in pursuing the issues of real importance, "Like, did we fake the moon landing? What really happened at Roswell? And where are Biggie and Tupac?"

    As Obama chided Trump, Seal Team Six was preparing for the raid that would lead to the killing of Osama Bin Laden, the following night.

    Speaking of Trump's own eminent qualifications for the presidency, Obama noted, "On Celebrity Apprentice, the men’s cooking team did not impress the judges from Omaha steaks, but you recognized that this was a lack of leadership, so you fired Gary Busey. These are the kinds of decisions that would keep me up at night. Well-handled, sir. Well-handled.”

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    Seth Meyers (2011)

    After Obama bruised Trump, Seth Meyers tagged in for the kill: "Donald Trump said that he was running for president as a Republican. That's funny, because I thought he was running as a joke."

    White House

    Jon Stewart (1997)

    Two years before he took the reins at "The Daily Show," Jon Stewart headlined the 1997 Correspondents Dinner. The jokes, for what it's worth, have aged about as well as the bushy, brown haired Stewart himself. An inordinate amount of time is spent ridiculing Senator Robert Byrd for his (apparently) notorious hatred of dogs. The performance is nonetheless compelling, for the way it captures, in embryonic form, the earnest sarcasm that eventually won Stewart the hearts of Blue America.

    White House

    Wanda Sykes (2009)

    In 2009, Wanda Sykes became the first African-American woman, and openly gay comedian, ever to perform at the dinner. She also delivered perhaps the most unabashedly partisan act in the history of the event.

    After teasing the new president and first lady about basketball skills and bare arms, Sykes shifted her focus to the right, and her tone to blistering. At this point, mere months into Obama's first term, Rush Limbaugh had already announced on his radio show that he hoped the Obama administration would fail. Sykes pointed out that this was akin to Rush saying he hoped America would fail. She then delivered a joke as controversial as it was brutal, speculating that Limbaugh may originally have been the 20th 9/11 hijacker -- only he was too stoned on oxycontin to show up.

    Concluding her thoughts on the voice of "Real America," Sykes opined, "Rush Limbaugh [says] ‘I hope the country fails.' I hope his kidneys fail. How about that? He needs some waterboarding, that’s what he needs."

    Real America wasn't amused.

    White House

    Bill Clinton (2000)

    In April, 2000, with Al Gore out running for president, and Hillary in New York campaigning for Senate, Bill Clinton had nothing to do but contemplate the bleak future of an enormously powerful, globally celebrated multi-millionaire. That year's dinner opened with this five minute video chronicling Clinton's lonely final days in the White House. While overlong and not technically a "performance," the surreality of a depressed Bill Clinton idly watching a staffer xerox his own head, more than justifies its inclusion in this slideshow.

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