Michelle Wolf Releases Set Roasting the White House Correspondents’ Dinner

In 2018, stand-up star and former Daily Show correspondent Michelle Wolf set the American news media ablaze with her burn of then-Press Secretary Sarah Huckabee Sanders at the White House Correspondents’ Dinner. Now that nobody is allowed to roast the powerful anymore at the WHCD, Wolf wants all the smoke.

When Wolf hosted the annual meeting of America’s most important political leaders and the journalists who are supposed to hold them accountable during Donald Trump’s first term as president, she unloaded a series of scathing smackdowns on the entirety of Washington, D.C. and its most influential citizens. But somehow, out of all the brutal roasts Wolf delivered to the frowning faces of the political elite, one of Wolf’s most mild burns of the night became the only line from the White House Correspondents’ Dinner to elicit multiple weeks of round-the-clock commentary in all the major news outlets — and Wolf has a pretty good idea of why that was the case.

Four years after the most divisive set of Wolf’s comedy career, Wolf secretly recorded a 15-minute routine that she performed to a cozy crowd in Denver, Colorado in which she addressed her White House Correspondents’ Dinner and told all the jokes that even she thought were too mean for the black-tie event. Well, in the wake of the White House Correspondents' Association firing would-be host Amber Ruffin ahead of this Saturday’s gala over Ruffin’s critical remarks about the Trump Administration, Wolf released the recording of her 2022 show Dinner Time exclusively on Punchup Live, revealing that Sanders and her smoky makeup were lucky that Wolf didn’t turn up the heat.

“A lot of people hated it, a lot of people loved it,” Wolf said of her set at the 2018 White House Correspondents' Dinner. “And, to be fair, that is the lane I like to be in, you know? I’d rather be loved or hated than someone who’s just like, ‘She’s fine.’” Wolf later added of the gala, ”I was under the impression that it was a roast, maybe I was wrong.”

While Wolf knew that her speech would be divisive, Wolf said that she took umbrage with how the media handled her politically provocative performance, specifically with how they focused on this remark she made about Sanders: “I actually really like Sarah. I think she’s very resourceful. 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.”

As Wolf clarified in Dinner Time, she was not, in fact, insulting Sanders’ looks with the jab, as so many politicians and political commentators claimed in the wake of the event. If anything, Wolf was praising the press secretary. “If we’re really categorizing things, that’s a compliment. I’m complimenting her eye makeup and her ingenuity of materials,” Wolf explained to the Denver crowd, pointing out that she actually did insult the appearances of many men that night, although no one batted a smoky eye when she made fat jokes at Chris Christie’s expense.

“The reason you can make jokes about men’s looks and no one gets mad at you is because no one ties men’s looks with their ability to do a good job,” Wolf stated plainly. “Now a woman, if you say that she’s ugly, because we’re so concerned with everyone being beautiful, when you say she’s ugly, they assume you’re saying she’s bad at her job. Which is crazy because we all know an ugly woman is always better at her job.”

“I don’t think Sarah was bad at her job, I think Sarah was actually very good at her job. She was press secretary, her job was to spin things. And she spun things so fast, she spun so much her one eye gave up,” Wolf cracked. “That is a joke about looks — or, look.”

Throughout Dinner Time, Wolf delivered plenty of punchlines that proved how, if she wanted to, she could have given everyone in Washington, D.C. an eating disorder with her burns about their appearances. Wolf teased the digs she didn’t deliver at the White House Correspondents’ dinner, including jokes such as, “Sarah Sanders looks like a young Mrs. Doubtfire.” And: “Sarah Sanders’ dad is Mike Huckabee and her mom is, I also think, Mike Huckabee.”

But really, the media backlash following the 2018 dinner was never about Wolf’s eye shadow joke. “I didn’t make fun of Sarah’s looks, but the reason they said I did is to distract from what I actually did,” Wolf explained. “What I actually did was call out the media for their relationship with Trump. I said, ‘You pretend you hate Trump, but I actually think you love him, because you’re profiting off of him.’ I think that was true then, I think it only got more true.”

Given how the White House Correspondents’ Association just axed Ruffin ahead of tomorrow’s capitulation ceremony, Wolf’s assessments of the media in 2018 and in 2022 may have actually been too generous.

“The media, the left, the right, the government in general, they don’t care what we do so long as we’re fighting one another,” Wolf argued. “Because as long as we’re fighting one another, we’ll never go after the real problem, which is them.”