White House Correspondents’ Dinner and the ‘Comedy Central Roast of Donald Trump’: What a difference seven years make

Comedian Michelle Wolf after the White House Correspondents' Dinner at a party hosted by Netflix's "The Break with Michelle Wolf."
(Tasos Katopodis / Getty Images for Netflix)

After another White House Correspondents’ Dinner in which an up-and-coming comic has been criticized for going too far, it’s worth considering what has changed about the lengths a comedian can go in their criticism of the Trump administration, which, as a reflection of its leader, continues to be remarkably thin-skinned.

Trump, like last year, skipped Saturday’s dinner, preferring the far friendlier reception of another campaign-style rally in Michigan. “Is this better than that phony Washington White House correspondents thing? Is this more fun?” he asked the crowd.

But it wasn’t always this way.

Consider, if you will, the year 2011. Anne Hathaway and James Franco presided over an Oscars ceremony that everyone was sure couldn’t get any stranger; the U.S. Senate deviated from the usual 10-year term limit to extend the tenure of then-FBI Director Robert Mueller, and Donald Trump, red tie and all, sat and smiled as a procession of entertainers (including, perplexingly, “Jersey Shore’s” Mike “The Situation” Sorrentino) insulted him for some 90 minutes on “The Comedy Central Roast of Donald Trump.”


Time often has a way of making the past seem ridiculous and — in some cases — eerily prescient, which is surely part of the reason the network pulled the program from its vaults for rebroadcast on Thursday, Friday and Sunday nights.

But another justification surely came with the correspondents’ dinner, a typically chummy, lighthearted affair where a sitting president presides over a meal with journalists while a comic makes jokes at their expense.

This year’s dinner featured “The Daily Show” alumna and host of an upcoming Netflix talk show, Michelle Wolf — whose HBO special last year was winkingly titled “Nice Lady” — and Trump’s absence did nothing to deter her in a barbed, fearless monologue that skewered his financial standing, the media, Democrats, MSNBC host Rachel Maddow and White House Press Secretary Sarah Huckabee Sanders, who attended the evening in the president’s place.

“I love you as Aunt Lydia on ‘The Handmaid’s’ Tale,’” Wolf said to Sanders, comparing her with Ann Dowd’s oppressive character in the Hulu series. “Mike Pence, if you haven’t seen it, you would love it.”

Sanders, seated to Wolf’s left, scowled, giving no indication she planned to be a good sport as the night’s most visible representative of the administration.

“I actually really like Sarah, I think she’s very resourceful,” Wolf went on. “She burns facts, and then she uses that ash to create a perfect smoky eye. Maybe she’s born with it, maybe it’s lies,” she added, referencing a cosmetics tag-line, “It’s probably lies.”


A sympathetic groan rippled through the crowd and Wolf grinned, undeterred, knowing her real audience wasn’t in the room; it was those watching at home. Plus, she had set the night’s ground rules with an early nod to the Stormy Daniels case: “As much as some of you might want me to, it’s 2018 and I’m a woman, so you cannot shut me up — unless you have Michael Cohen wire me $130,000.”

Some of the media and political figures in attendance later accused the comic of going too far. For Wolf, this can only be received as the laurels of a roast well done given previous correspondents’ dinner comics — such as Stephen Colbert in 2006 — who have heard similar criticism. And he turned out all right (though the dinner fared worse the next year with the less edgy Rich Little on hand).

In the ultimate stamp of approval, Trump offered his own critique Sunday morning, referring to Wolf as the “so-called comedian” in calling the dinner “a very big, boring bust” from the relative safety of Twitter.

What a difference seven years make. Whether it was age, power or repeated exposure to ridicule that wore Trump’s skin down, the future president appeared on some level to be in on the joke during Comedy Central’s “Roast” — or at least willing to pretend to be so in the name of furthering his wealth, his fame or, as referenced numerous times, his political ambitions.

The Trumpian touchstones featured in the opening credits of “The Roast” (whose conceit follows a day-in-the-life of Trump from his point of view, though he clearly wasn’t involved in their creation) are immediately familiar and jarring: There’s the branded helicopter, the brief but pointed glance from a young blonde who shares his limo ride to Trump Tower, where deals are struck and campaign posters approved. As he leaves, he gets a kiss from a beauty queen.

Once the show begins, he enters on a golden golf cart flanked by sash-wearing models amid a shower of cash, giving every impression of being not just on board with being the night’s target but reveling in it.

If there has been one constant in Trump’s public life, it’s his fondness for celebrity (witness how quickly he has embraced Kanye West’s praise on social media this week). And while his 2011 roast didn’t entirely draw from the comic A-list — in addition to Sorrentino, there’s the network ringer Jeffrey Ross, Snoop Dogg, Larry King, Lisa Lampanelli and future executive producer of the Trump-sympathizing “Roseanne” revival, Whitney Cummings — a spotlight is a spotlight, and Trump weathers every insult. At one point, he even briefly puckers his face into a play on the then-common impression of him on “SNL” after it’s referenced.

It’s a far cry from the behavior of Trump the president, who keeps his TV appearances primarily confined to the friendly, open-ended exchanges on “Fox & Friends.”

There are the jokes about his hair, his wealth and his fondness for young women, (which after the “Access Hollywood” tape and the Daniels news now takes on a darker cast). But one of the roast’s most favored topics is his turn toward politics, which at that point was just beginning.

“It’s pronounced ‘I am [expletive] delusional,’” host Seth MacFarlane advises him, “Not ‘I am running for president.’” And, oh, how they laughed.

“Donald says he wants to run for president and move on into the White House,” Snoop tells him during his sharply timed turn at the mic. “Why not? It wouldn’t be the first time he pushed a black family out of their home.” The crowd ohhs, the camera finds an amused Ivanka Trump covering her face, and all along, Trump just smiles. “Nice going, great job,” Trump tells Snoop with a pat on the back after his set is through.

And because it’s all sport, the good cheer feels mutual. “Nice to meet you, it’s a pleasure!” Cummings genially says before her turn, and every performer says something kind after their round of barbs. Seven years later, Snoop has been among Trump’s many targets on Twitter, where last year he called the hip-hop star’s career “failing” after he released a Trump-skewering music video.

It’s not just a question of whether Trump would now share a stage with these comics, but whether the feeling would be mutual amid a consistently pugnacious presidency.

Though it seems debatable whether Trump actually enjoyed himself during the roast (Cummings appeared on Larry King’s show in 2017 to discuss that very thing), he undoubtedly enjoyed its conclusion, when, according to tradition, the target gets the last word. He throws some insults of his own, complete with the familiar off-script asides, which generate the usual uproarious stage laughter in return. He even kills the crowd with a profane joke about his hair, which he begrudgingly accepts with a repeated, “OK, very funny.”

But as the show closes, Trump the campaigner arrives, seemingly from the future. Teasing a run that never materialized in 2012, he promises the crowd, “You will have the great pleasure of voting for the man that will easily go down as the greatest president in the history of the United States: Me.”

Time will tell who has the last laugh on that one.

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