FLASHBACK: Five of the most politically-charged moments at the White House Correspondents' Dinner
The worlds of politics and the media are colliding Saturday with Donald Trump's attendance at the White House Correspondents' Dinner (WHCD) for the first time as president.
The annual gala that celebrates the First Amendment and awards journalism scholarships has gotten increasingly polarizing in recent years, so much so that Trump had boycotted the century-old event during his previous years in office.
Here are five memorable moments from the WHCD:
Stephen Colbert made a big splash at the 2006 WHCD with a "special edition" of "The Colbert Report," the Comedy Central program starring Colbert with a right-wing persona that made him a household name.
He offered tongue-in-cheek praise for his "hero," President George W. Bush, all while in character.
"It's my privilege to celebrate this president," Colbert said. "We're not so different, he and I. We get it. We're not brainiacs on the nerd patrol. We're not members of the factinista. We go straight from the gut, right sir? That's where the truth lies, right down here in the gut."
"I believe the government that governs best is the government that governs least. And by these standards, we have set up a fabulous government in Iraq," he later jabbed.
He took aim at Bush's poor approval rating, telling the president, "Guys like us, we don't pay attention to the polls. 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's biting monologue redefined how aggressively comedians go after the sitting president — at least when it's a Republican.
The last WHCD Trump attended was in 2011, when the country only knew him as a celebrity real estate mogul and host of "The Apprentice." However, he was the target of intense mockery by President Barack Obama and comedian Seth Meyers over his outspoken skepticism that Obama was born in the U.S. and called for the release of his birth certificate. Days before the WHCD, the State of Hawaii released Obama's long-form birth certificate proving his citizenship.
"Donald Trump is here tonight," Obama said to the room filled with the Washington elite. "Now I know he's taken some flak lately, but no one is happier, no one is prouder to put this birth certificate matter to rest than The Donald. And that's because he could finally get back to focusing on the issues that matter — like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?"
"All kidding aside, obviously we all know about your credentials and breadth of experience," Obama further jabbed at Trump before poking fun at his "Celebrity Apprentice" gig and mocking the "change" he'd bring to the White House, suggesting he'd overhaul it into a hotel and casino.
Meyers then took to the podium to roast Trump.
"Donald Trump has been saying that he will run for president as a Republican, which is surprising since I just assumed he'd be running as a joke," Meyers quipped, sparking huge laughs from the audience as the camera was aimed at a stern-faced Trump.
"Gary Busey said recently that Donald Trump would make a great president. Of course, he said the same thing about an old, rusty birdcage he found," Meyers later continued. "Donald Trump recently said that he has a great relationship with the Blacks, though unless the Blacks are a family of White people, I bet he's mistaken."
Many have speculated that moment spurred Trump's ambitions to seek the Oval Office.
In 2018, Trump's then-White House press secretary Sarah Huckabee Sanders was sent to represent the administration at the WHCD after Trump decided to skip the event for a second year in a row.
Huckabee Sanders sat on the dais as the WHCA's hand-picked entertainer, far-left comedian Michelle Wolf, leveled personal jabs at the Trump spokeswoman.
"I actually really like Sarah. I think she's very resourceful. Like she burns facts, and then she uses that ash to create a perfect smoky eye," Wolf said. "Like, maybe she's born with it. Maybe it's lies. Probably lies."
She continued, "And I'm never really sure what to call Sarah Huckabee Sanders, you know. Is it Sarah Sanders? Is it Sarah Huckabee Sanders? Like, what's Uncle Tom, but for white women who disappoint other white women?"
Wolf was roundly criticized, even by members of the press. The backlash against was so swift that the WHCA chose a historian to be a keynote speaker at the dinner instead of another comedian the following year.
During the 2024 WHCD, "Saturday Night Live" star Colin Jost gently poked fun at President Joe Biden while saving his brutal jokes towards Trump.
However, Jost put jokes aside for the last several minutes of his monologue to offer a sentimental message for the Democratic president, who at the time was still seeking reelection.
"I lost my grandfather this year, as you alluded to, of a firefighter, William Kelly. He’s the reason that our son’s middle name is William. He helped raise me growing up, and I would not be here today without him," Jost told Biden. "You remind me of him. Some of your best qualities remind me of his."
The "Weekend Update" anchor stopped short of offering a full-fledged endorsement of the embattled incumbent.
"My grandfather, a Staten Island firefighter, voted for you, Mr. President," Jost said, sparking applause from the liberal crowd. "He voted for you in the last election that he ever voted in... He voted for you, and the reason that he voted for you is because you’re a decent man. My grandpa voted for decency. And decency is why we are all here tonight. Decency is how we’re able to be here tonight."
"So Mr. President, I thank you for your decency on behalf of my grandfather," Jost added.
At last year's dinner, Axios reporter Alex Thompson accepted the Aldo Beckman Award for Overall Excellence in White House Coverage for his reporting that shed light on Biden's cognitive decline long before his now-infamous presidential debate performance that led to his ousting from the 2024 race.
"Being truth tellers also means telling the truth about ourselves. And some people trust us less because of it," Thompson told his peers at the dinner. "We, myself included, missed a lot of this story. We bear some responsibility for faith in the media being at such lows."
WHITE HOUSE REPORTERS RESPOND AFTER BEING CALLED OUT FOR WEAK COVERAGE OF BIDEN'S DECLINE AT WHCD
"I say this because acknowledging errors builds trust, and being defensive about them further erodes it. We should've done better," Thompson added.
Thompson's speech made waves in Washington, D.C., sparking debate among journalists about whether there was sufficient coverage of Biden's decline before his abrupt exit from the presidential race.