Over the weekend, Stephen Colbert said that he would “love” to again headline a White House Correspondents Association dinner — the April 29 event that will be the first during the administration of Donald Trump.
Whether he was joking or not, it does raise the question of just who will take on the role of featured entertainer at the annual gathering.
Headlined by Larry Wilmore, Cecily Strong and Joel McHale in recent years, it’s at once one of the highest profile gigs of the year and among the most challenging. Performers follow the president on stage, in a cavernous ballroom filled with journalists, politicians and celebrities who have no shortage of opinions.
The task may be even more perilous this year. If Trump attends the dinner, as every president has for more than 35 years, a comic will face the question of how hard or soft to go on the commander in chief who has responded to satirical bites with attacks of his own — such as his Twitter diatribes against “Saturday Night Live.”
Add to that a heightened scrutiny to the White House press corps and how it covers Trump, who has already said that he is at “war” with the media while his adviser has labeled it the “opposition.” Last week, representatives for Vanity Fair and The New Yorker said that they would be bypassing their sponsorship of events tied to the WHCA dinner this year, while some other media organizations are said to be still weighing their participation.
“In the past, the big challenge for comedians was, ‘How could I be funnier than President Obama? In most years, his comedy trumped the comedians,” said Dave Berg, producer of “The Tonight Show with Jay Leno.” “This year goes way beyond that. On the one hand, you could be accused of sitting there and skewering Trump and he is captive [at the dinner]. On the other hand, you could be accused of being too soft.”
An insider who has worked closely on the dinner said that “You would think that it would be easy to get a comedian for the dinner — with this big crowd and the prestige — but it’s really hard and it takes up an inordinate amount of time and it’s really hard to get a commitment.”
But the source does think that it will be a unique chance for an entertainer to make a mark.
“This is a great opportunity, because every comic out there is doing commentary on Trump anyway. Here is a chance to do their material and right in front of him. This is an opportunity to do something new.”
The job of selecting and securing the entertainer falls on the president of the WHCA, and that task this year falls on Jeff Mason, White House correspondent for Reuters. He said that he had no updates on the entertainer yet, or the time frame for announcing who that will be.
Julie Mason, host of SiriusXM’s “Press Pool” and a former WHCA board member, said that when it comes to selecting an entertainer, a “good default is TV people, who are good at satire and family-friendly humor. But they are usually doing live shows themselves, or uninterested in the risk of hosting.”
She said that the association doesn’t have to be bound to having a comedian entertain. Singers used to perform for the event, and Barbra Streisand did one year, she noted. “Completely rethinking the entertainment might be fun,” she said. “But I mean it’s not like there isn’t enough going on already.”
Patrick Gavin, director and producer of the 2015 documentary about the event, “Nerd Prom: Inside Washington’s Wildest Week,” said via email that the “reason this is a tough decision for a comedian is because, if they’re too tough on Trump, they run the risk of violating the ‘singe, but not burn’ principle that guides the dinner (they also run the risk of perhaps not getting the gig in the first place). And if they’re too soft — or soft at all — they will suffer the wrath of half of the country that view taking it to Trump as nothing short of a civic requirement.”
At the WHCA dinner in 2006, Colbert, in his conservative character, gave an especially biting satire of Bush while the president was sitting on the dais right there. It certainly boosted Colbert’s profile, but a big chunk of the audience seemed to react in awkward discomfort. The next year, the WHCA seemed to respond with the safest of safe choices: veteran impressionist Rich Little.
“The choice of comedian could by itself determine whether President Trump comes at all,” Gavin said. “I can’t imagine Trump being interested in taking grief from an edgy comedian and just taking it for an hour.”
There already is some early concern as to whether Trump will attend, or wait until the last minute before making a decision as he continues a war of words with the media. “We don’t want it to turn into a circus over whether the president is going to come or not,” said the insider.
For decades, it’s been a given that each year the WHCA invites the president to attend, and he accepts.
The last president to miss a dinner was Ronald Reagan in 1981, who was recovering at Camp David after an assassination attempt just 27 days earlier in front of the Washington Hilton (which is also the WHCA dinner venue). Reagan did, however, make remarks by phone.
Will Trump upend tradition?
He certainly knows the event — perhaps all too well. One of the most famous moments of any dinner came in 2011, when President Barack Obama skewered Trump, after Trump had drawn loads of media attention for calling into question whether Obama was born in the United States. Trump sat stone faced as Obama rattled off one-liners, and some who know Trump say it was a pivotal moment in his political career. Roger Stone, who had been an adviser to Trump’s campaign, told PBS’s “Frontline” last year that “I think that is the night he resolves to run for president.”
Yet at this dinner, Trump will be tasked with an unusual role — making fun of himself. Like the WHCA dinner, the Al Smith dinner has traditionally been a place for politicians to make jokes at their own expense. When Trump appeared at the event in October along with his rival Hillary Clinton, he told a few jokes but then offered a few campaign-style attack lines. He was booed.
Trump’s presence or non-presence also could drive who attends and who does not.
The dinner itself is to raise money for scholarships and to give awards to journalists, but that purpose often lost in the surreal mix of politicians, news media figures and Hollywood celebrities — easily filling the ballroom of the Washington Hilton to capacity. Figures like Tom Brokaw have called out the event as an excessive display that was sending a bad message to the rest of the country.
This year, some Hollywood figures are wondering how the news media will look if its members are mingling with a president who so routinely attacks them. Beau Willimon, the creator of the American version of “House of Cards,” tweeted that the “press should boycott altogether. Or leave when he speaks. He has zero respect for press. Why give him this platform?”
Others are moving forward with plans. Samantha Bee announced last week that she will host a event on the same evening called “Not the White House Correspondents Dinner.”
Jay Sures and UTA, who last year hosted a party on the night before the dinner with Funny or Die, have committed to hosting another one.
Responding to inquiries about the dinner, Jeff Mason recently released a statement saying that “this year, as we do every year, we will celebrate the First Amendment and the role an independent press plays in a healthy republic.”
Ed Chen, a former WHCA president, said that he actually was inundated with requests from agents pitching their clients for the 2010 dinner.”Everything short of bribery,” he said.
The situation may be different this year, but Chen also questions the need for an entertainer at the dinner at all. In years past, some attendees have headed for the exits right after the president’s remarks to get a good spot in the valet line, passing up the comic who comes out on stage.
