Correspondents’ Dinner’s biggest moments involve laughs, cringing and high-stakes politics

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This article was published 24/04/2026 (183 days ago), so information in it may no longer be current.

The White House Correspondents’ Dinner has had multiple iterations since it began a few years after World War I.

Washington’s premier soiree on Saturday is most identified by its modern form: a red carpet for the capital’s journalism elite, political staffers and an assortment of American business leaders and celebrities — with the leader of the free world and a comedian offering roasts.

Some years are forgettable and relegated to C-SPAN archives. Others produce viral moments — funny, cringeworthy or undeniably tense — and endure across social media.

Here’s a look at some of that history as Donald Trump prepares for the first time to attend as president:

Ronald Reagan once gave up the chance to rebut a comedian

As a former Hollywood actor, the 40th president had a magnetic stage presence and easy manner with a joke, and it was during Reagan’s presidency that comedians became an annual part of the dinner.

In 1983, Mark Russell, whose satire was a PBS staple, offered relatively tame jabs at Reagan. “There is another speaker following me,” he opened, “and so it is quite an honor for me to be doing the warmup for my chief writer here.”

When it was the president’s turn, Reagan demurred. He reminded the audience that he’d made “a sad journey” to Andrews Air Force Base earlier that day to receive the remains of the Americans killed in the April 18 bombing of the U.S. Embassy in Lebanon.

“I realize the original plan was that I would, in a sense, sing for my supper. In fact, I was prepared, not really to sing, but to do what you expected,” Reagan said, before explaining that it would be inappropriate for him to deliver humorous remarks. “If you’ll forgive us,” he said, “I’ll keep my script, and I hope you’ll give us a rain check, and it’ll still be appropriate next year.”

Dana Carvey and George H.W. Bush: A rare friendship

Presidents have been lampooned on NBC’s “Saturday Night Live” since Chevy Chase first depicted Gerald Ford in 1975. But Dana Carvey and President George H.W. Bush set the standard.

Carvey, who also played the iconic Church Lady, embellished the 41st president’s nasal tone and patrician air to caricature his signature phrases: “Not gonna do it. Wouldn’t be prudent.”

Bush became a fan. He and Carvey sat together at Bush’s last dinner as president, in 1992. After he lost to Bill Clinton that November, the president invited Carvey to the White House for a Christmas party. The two remained friends.

George W. Bush jokes about weapons of mass destruction

In 2004, American forces remained in Iraq after the 43rd president ordered an invasion based on assertions that Saddam Hussein had weapons that threatened U.S. security.

By the time of the annual dinner, it was apparent those claims were overblown. Bush made light of the situation with pictures of him looking around the White House for Saddam’s weapons.

“Those weapons of mass destruction have got to be here somewhere,” he said as one slide showed him looking under furniture in the Oval Office.

The audience laughed and applauded. Some veterans, including then-Sen. John Kerry, a 2004 presidential nominee, were not amused. Bush defeated Kerry that November anyway.

Colbert skewers Bush and the media

Not long into his second term, Bush sat uncomfortably as Stephen Colbert, then a Comedy Central host, hammered him with an aggressiveness unusual for the dinner.

“The greatest thing about this man is he’s steady,” Colbert said in 2006. “You know where he stands. He believes the same thing Wednesday that he believed on Monday, no matter what happened Tuesday. Events can change; this man’s beliefs never will.”

He sarcastically urged Bush to ignore his approval ratings, then in the low 30s: “We know that polls are just a collection of statistics that reflect what people are thinking in reality. And reality has a well-known liberal bias.”

Colbert lambasted the dinner hosts, too, suggesting Washington media protected the Bush administration.

“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,” Colbert said, “and you had the courtesy not to try to find out.”

A Trumpian dinner without Trump

During his first White House term, Trump broke the long streak of presidential attendance. Comedian Michelle Wolf targeted him anyway.

“It’s 2018, and I’m a woman, so you cannot shut me up — unless you have Michael Cohen wire me $130,000,” she cracked, referencing payments made to keep an adult film star from disclosing her allegations of a sexual encounter with Trump.

When the audience groaned at her crassness, Wolf quipped, “Yeah, shoulda done more research before you got me to do this.”

With Trump absent, his press secretary and now-Arkansas Gov. Sarah Huckabee Sanders sat at the head table and at the center of Wolf’s routine. Wolf compared Sanders’ role for Trump to being a character in “The Handmaid’s Tale,” a dystopian novel about an authoritarian, misogynistic society.

Her harshest barb riffed on a famous Maybelline mascara ad.

“I actually really like Sarah. I think she’s very resourceful,” Wolf said. “But she burns facts and then she uses that ash to create a perfect smoky eye. Like maybe she’s born with it; maybe it’s lies. It’s probably lies.”

Trump, who was in Michigan, called the routine “disgusting.”

Within hours, the Correspondents’ Association issued a statement saying the dinner is meant to celebrate “our common commitment to a vigorous and free press while honoring civility, great reporting and scholarship winners” and saying Wolf’s monologue “was not in the spirit of that mission.”

Sanders rekindled the moment earlier this year at Washington Gridiron, another annual politics-journalism event. “I’m proud to note that color has really taken off,” she said. “In fact, it’s the exact same thing worn by Vice President JD Vance.”

Obama vs. pre-presidential Trump

Despite not yet attending as president, Trump’s had his moment at the dinner.

In 2011, he helped lead the birther movement against then-President Barack Obama. Trump used social media and frequent Fox News Channel appearances to push the false narrative that the first Black president was born in Kenya and not a natural-born U.S. citizen.

But at the Washington Hilton, Obama had the lectern — and he used it with Trump sitting in front of him.

“Tonight, for the first time, I am releasing my official birth video,” Obama deadpanned, before showing the opening scene of Disney’s “The Lion King,” when the royal cub Simba is presented on the savanna.

Obama then turned his fire directly on the reality TV star.

“No one is happier, no one is prouder to put this birth certificate matter to rest than the Donald,” Obama said. “And that’s because he can finally get back to focusing on the issues that matter. For example, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”

As cameras captured a dour Trump, Obama mocked Trump’s role on “Celebrity Apprentice.”

“We all know about your credentials and breadth of experience,” the president said, marveling that Trump had to decide who to blame when “the men’s cooking team cooking did not impress the judges from Omaha Steaks.”

“These are the kind of decisions that would keep me up at night,” Obama concluded. “Well handled, sir. Well handled.”

Trump glared icily.

By November 2012, as Obama prepared for his second term, Trump had filed a trademark application for the phrase he would emboss in the national culture four years later: “Make America Great Again.”