Meanwhile, the president assured his audience in MI that he would rather be there than at the dinner. But she reserved a considerable portion of her set for roasting White House press secretary Sarah Huckabee Sanders and White House counselor Kellyanne Conway, who took the president's place on the dais. She noted Trump's decision to avoid the dinner by saying, "It turns out Trump is the one (expletive) you're not allowed to grab".
There was a mixed reaction from the press corps itself - with some describing the jokes about Sanders as "cruel" and "mean".
Many administration officials, including the president himself, became the butt of the joke. When former press secretary Sean Spicer tweeted that the dinner "was a disgrace", Wolf replied, "Thank you!"
Wolf's performance, in particular the Huckabee Sanders material, sparked outrage from the conservative class and left some in the Washington media questioning the event's decorum.
In a "roast" that drew both laughs and gasps, Wolf started by saying: "We are graced with Sarah's presence tonight. Like a porn star says when she's about to have sex with Trump, let's get this over with", the first of many bawdy insults.
The comedian caused more controversy with a quip referring to her make-up: "I actually really like Sarah".
"The press has done a lot of incredible work this year. a lot of that was overtaken by a skit that wasn't very amusing and we sometimes celebrate ourselves too much, I think. She burns facts and uses the ash to create a ideal smokey eye", Wolf said. If you don't give her a platform, she has nowhere to lie. It has nothing to do with her looks. What happened to women power and women stick together? To the many thousands of people who couldn't get in, I cherish you.
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"I'm not suggesting she gets hurt", Wolf followed up.
"While Washington, Michigan, was a big success, Washington, D.C., just didn't work", wrote Trump, who continued his break with tradition in not attending the media confab. Trump continues to use his presidential platform for mere pleasantries.
But there was a fierce response on social media from people who said, in essence, the correspondents association hired an edgy comedian. "It's probably lies", Wolf said. "It's not just the White House", Scaramucci said on "Reliable" Sunday.
Columnist Mehdi Hasan also pointed to allegations against the president - including multiple claims of sexual harassment, which he denies.
Wolf managed Saturday night to scandalize the majority of Washington's tuxedo-clad intelligentsia with a barrage of bon mots that, in the eyes of much of the press and political establishment, weren't really so bon at all.
His explanation of the word "covfefe" in a tweet by Mr Trump sparked incredulity.