In response to the announcement, Wolf referred to the association as a bunch of “cowards” in a tweet. “The media is complicit,” she wrote. “And I couldn’t be prouder.”
During her set in April, Wolf spread the jokes around, roasting the Trump administration and the media in equal measure. Anyone familiar with her comedy shouldn’t have been surprised at her scathing, take-no-prisoners approach.
“So-called comedian Michelle Wolf bombed so badly last year at the White House Correspondents’ Dinner that this year,” Trump tweeted Tuesday. “For the first time in decades, they will have an author instead of a comedian. Good first step in comeback of a dying evening and tradition! Maybe I will go?”
Wolf responded on Twitter, “I bet you’d be on my side if I had killed a journalist. #BeBest," referencing the president’s support of Saudi Arabia following last month’s brutal killing of journalist Jamal Khashoggi at a Saudi Consulate. (“Be Best” is First Lady Melania Trump’s anti-bullying campaign.)
Although intended to be a scholarship dinner celebrating the First Amendment, the insular and nerdy Washington tradition has in recent years morphed into a more national spectacle, with random celebrities flooding the city, journalists and the people they cover getting drunk at parties, and comedians and the president delivering speeches broadcast on C-SPAN and cable.
But the aims of a comedian — to roast the people in the room, including the president — don’t always fit the event.
The dinner is an incredibly high-profile gig that can boost the star power of a comedian who does well. But it’s also a high-wire act: Performers balance wanting to effectively skewer the president and the media while getting everyone to laugh at themselves, with telling jokes that are daring enough to earn the respect of your comedy peers.
"I wasn’t expecting this level [of controversy], but I’m also not disappointed there’s this level,” Wolf told NPR shortly after her set. “I knew what I was doing going in. I wanted to do something different. I didn’t want to cater to the room. I wanted to cater to the outside audience and not betray my brand of comedy.”
Among comedians, the setting has long been considered a perfect storm of bad-comedy-room elements. The dinner goes down in the Washington Hilton ballroom and the audience is trying to eat while wearing uncomfortable clothes.
“It’s a terrible room. It is cavernous. People have bad sight lines,” Seth Meyers, who performed in 2011, told The Washington Post. “I feel as though the audience is half-listening to you, and half-listening to how people are reacting to you. Just constantly checking in with other people at their table. I bet a factory that makes forks, is quieter in terms of silverware noises in that room.”
But, Meyers added, “everybody who goes into it knows what the challenges are, and that’s what makes it exciting to do for a comedian.”
Jimmy Kimmel, who performed in 2012, has compared it with “going to the movies and it’s like wedding seating. Nobody is going to be paying full attention to the movie. You want people at the very least to be paying attention to what you say.”
The dinner has almost always had comics, except in 1999, when Aretha Franklin performed, and in 2003, when Ray Charles took the stage. And since the speeches began airing on C-SPAN in 1993, a dynamic has emerged: While edgy jokes can fall flat in the uptight room of people with fragile egos, they can crush with the viewing audience at home.
Stephen Colbert’s infamous 2006 set, performed as his conservative alter-ego, amounted to a takedown of the George W. Bush administration and the media in the lead-up to the Iraq War. “The president makes decisions. He’s the decider,” Colbert said while in character. “The press secretary announces those decisions, and you people of the press type those decisions down.”
The crowd in the Hilton ballroom that year ranged from uncomfortable to downright offended, and plenty of Washington types attacked Colbert for going too far — which liberals said demonstrated the problematic relationship between the White House and the media. In the years since, Colbert’s set transformed from controversial to iconic.
After Colbert, the WCHA opted for the safest of bets by enlisting impressionist Rich Little.
“I loved Colbert and thought he was outstanding,” then-WHCA President Steve Scully told The Post in 2007. “But some people don’t get his brand of humor. Do you want to invite someone to a party and make them into a political piñata? That’s not the purpose of the dinner. It’s for [journalists] and their sources and contacts to have an enjoyable evening. That’s what we’re trying to do."
In 2009, Wanda Sykes received considerable criticism after her set at the dinner, in which she told some pretty scathing jokes about Rush Limbaugh, including one with a reference to 9/11.
White House press secretary Robert Gibbs tried to distance President Barack Obama from the set at the time and told reporters, “I think there are a lot of topics that are better left for serious reflection rather than comedy. I think there’s no doubt that 9/11 is part of that."
Sykes had no regrets. “I wouldn’t change anything,” she told Metro Weekly. “I just know a lot of people were in the room, and they were all laughing, so I think there’s a little hypocrisy there.”
Larry Wilmore has said he knew he lost the room early on during his 2016 set — which closed with a word that sparked a bunch of controversy itself — but he was “actually surprised at the reaction in the room.”
“I thought it was my job to make barbs about the president, politicians and the media, and to make pointed jokes,” he told The Post in 2016. “I knew people were not laughing, but I felt like I was doing my job up there. This is what you hired me to do. . . . You never want to defend a joke. People get to choose whether or not to laugh and whether or not they think something is funny."
The spectacle of the media and political elite hobnobbing in the nation’s capital has always left some journalists uncomfortable. Any sort of simmering discomfort with the whole affair became abundantly clear during the Trump era. In the past, the president has nearly always attended the annual dinner and gives a speech, showing they can take comedic hits and dish them out. Trump, however, has skipped the dinner since taking office and made a big thing of it by holding rallies in Pennsylvania and Michigan instead. Trump suggested he may attend after the association’s decision to nix comedy.
Hasan Minhaj recalled that while at the 2017 dinner, he kept reflecting on how the event was meant to honor the First Amendment.
“This is insane. The president of the administration has abused the First Amendment,” Minhaj, who performed that year, told Vanity Fair. “Our president tweets whatever comes into his mind, and he doesn’t even want to honor the amendment that allows him to do it? . . . The hypocrisy of that sort of helped shape the narrative and the arc that I wrote for the speech.”
But after Wolf’s set, many saw the WHCA as guilty of hypocrisy. Then-President Margaret Talev said the program “was meant to offer a unifying message about our common commitment to a vigorous and free press while honoring civility, great reporting and scholarship winners, not to divide people . . . Unfortunately the entertainer’s monologue was not in the spirit of that mission.”
When it comes to a difficult audience, “as a comedian, you get what you get,” Meyers said. “But it seems like the people who invite you and basically task you with entertaining a room should stand by you.”
This story, originally published Nov. 20, has been updated.