White House Correspondents Dinner: A journey through its most controversial and funny moments

The White House Correspondents' Dinner, an annual fixture in Washington’s social calendar, has evolved significantly since its inception shortly after the First World War. What began as a gathering for journalists has transformed into a glittering red-carpet affair, drawing together the capital’s media elite, political figures, business leaders, and celebrities, all converging to witness the US leader and a comedian deliver their respective roasts.

While some editions of the dinner fade into obscurity, relegated to C-SPAN archives, others generate indelible viral moments – whether humorous, cringeworthy, or undeniably tense – that resonate across social media for years. As Donald Trump prepared to attend the event for the first time as president, a look back at some of its most memorable instances offers insight into its unique place in American political culture.

One notable occasion saw Ronald Reagan, a former Hollywood actor renowned for his magnetic stage presence and easy wit, forgo the opportunity to deliver humorous remarks. It was during his presidency that comedians became an annual fixture at the dinner. In 1983, satirist Mark Russell, a PBS staple, offered relatively gentle jabs at Reagan.

President Ronald Reagan watches as first lady Nancy Reagan comments from the podium during the White House Correspondents' Association annual dinner on April 23, 1987, in WashingtonAP Photo/Charles Tasnadi

"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." However, when it was the president's turn, Reagan demurred. He reminded the audience of a "sad journey" he had made earlier that day to Andrews Air Force Base to receive the remains of Americans killed in the 18 April bombing of the US Embassy in Lebanon.

"I realise 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 stated, explaining that it would be inappropriate to deliver humorous remarks. "If you’ll forgive us," he concluded, "I’ll keep my script, and I hope you’ll give us a rain check, and it’ll still be appropriate next year."

Another unique dynamic emerged between Dana Carvey and George H.W. Bush. Presidents have been lampooned on NBC’s "Saturday Night Live" since Chevy Chase first depicted Gerald Ford in 1975, but Carvey and the 41st president set a distinct standard.

Carvey, also known for his iconic Church Lady character, masterfully exaggerated Bush’s nasal tone and patrician air, caricaturing his signature phrases like: "Not gonna do it. Wouldn’t be prudent." Bush became a fan, and the two sat together at Bush's final dinner as president in 1992. After his defeat to Bill Clinton that November, Bush invited Carvey to the White House for a Christmas party, and their friendship endured.

Comic Dana Carvey, left, shows President George H.W. Bush how to imitate himself, Dec. 8, 1992, at the White House in WashingtonAP Photo/Dennis Cook

The dinner also provided a platform for more controversial humour. In 2004, with American forces still in Iraq following the 43rd president’s invasion based on assertions of Saddam Hussein possessing weapons threatening US security, the claims were increasingly seen as overblown. George W Bush made light of the situation with a series of pictures showing him searching the White House for Saddam’s weapons.

"Those weapons of mass destruction have got to be here somewhere," he quipped as one slide depicted him looking under Oval Office furniture. The audience responded with laughter and applause, though some veterans, including then-Senator John Kerry, the 2004 presidential nominee, were reportedly unamused. Bush went on to defeat Kerry that November.

Not long into his second term, George W. Bush endured an uncomfortably aggressive roast from Stephen Colbert, then a Comedy Central host, in 2006. "The greatest thing about this man is he’s steady," Colbert declared. "You know where he stands. He believes the same thing on 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 disregard 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 also lambasted the Washington media, suggesting they 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."

President George W. Bush laughs as comedian Jay Leno tells jokes at the annual White House Correspondents Association Dinner in Washington, on May 1, 2004AP Photo/Gerald Herbert

During his first White House term, Donald Trump broke the long-standing tradition of presidential attendance. Nevertheless, comedian Michelle Wolf targeted him in 2018. "It’s 2018, and I’m a woman, so you cannot shut me up — unless you have Michael Cohen wire me $130,000," she joked, referencing payments made to an adult film star. When the audience groaned, Wolf retorted, "Yeah, shoulda done more research before you got me to do this."

With Mr Trump absent, his press secretary, Sarah Huckabee Sanders, now Arkansas Governor, sat at the head table and became the focus of Wolf’s routine. Wolf compared Sanders’ role to a character in "The Handmaid’s Tale," a dystopian novel. Her harshest barb riffed on a famous Maybelline mascara advertisement: "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." Mr Trump, who was in Michigan, called the routine "disgusting."

Within hours, the Correspondents’ Association issued a statement asserting the dinner was meant to celebrate "our common commitment to a vigorous and free press while honoring civility, great reporting and scholarship winners," adding that Wolf’s monologue "was not in the spirit of that mission." Sanders later rekindled the moment at another event, stating: "I’m proud to note that color has really taken off. In fact, it’s the exact same thing worn by Vice President JD Vance."

Donald Trump boards Air Force One during his departure from Andrews Air Force One Base, Md., April 28, 2018. Trump traveled to Michigan to speak at a rally on the same night as the White House Correspondent's Dinner, the second straight year Trump as skipped the event with the White House Press CorpsAP Photo/Pablo Martinez Monsivais

Even without attending as president, Donald Trump had a memorable moment at the dinner. In 2011, he was a prominent voice in the birther movement against then-President Barack Obama, using social media and Fox News appearances to push the false narrative that the first Black president was born in Kenya. However, at the Washington Hilton, Obama held the lectern, with Mr Trump seated directly 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.

Obama then turned his attention directly to 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 visibly dour Mr Trump, Obama mocked his role on Celebrity Apprentice. "We all know about your credentials and breadth of experience," the president said, marvelling that Mr 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." Mr Trump glared icily. By November 2012, as Obama prepared for his second term, Mr Trump had filed a trademark application for the phrase he would emboss in the national culture four years later: "Make America Great Again."