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Steven Portnoy previews White House Correspondents' Dinner
02:56 - Source: CNN
CNN  — 

It was 2014 and Diamond Joe was having a moment.

The muscle-car-revving, hair-metal-blasting party animal, conceived as satire by The Onion as Joe Biden’s alter-ego, had suddenly become the toast of Washington – never mind the actual Joe Biden doesn’t drink and has remained happily married for four decades.

Still, the best comedy contains truths. Though he’d later come to resent the “goofy uncle” label, Biden was willing to be in on the joke for a little while. And so, on a spring afternoon, he found himself sitting in a canary yellow Corvette Stingray, aviator sunglasses in place, filming a video for the annual White House Correspondents’ Dinner with his fictional “Veep” equivalent played by Julia Louis-Dreyfus.

“He was really game for that. He sort of understood what was funny about himself,” said David Litt, a speechwriter who helped shepherd the video crew on Biden’s shoot through the Oval Office.

Eight years later, Biden is preparing to deliver his own high-profile routine at this year’s correspondents’ dinner, his first outing as a live comedian-in-chief and the highest-profile opportunity to showcase what people close to him insist is a “genuinely good” sense of humor.

“The President has a very good sense of humor and is working hard on his own speech,” press secretary Jen Psaki said Friday.

Still, Biden is playing to a tough room at a tough moment. And while he’ll happily poke fun at his quirks – real and perceived – at heart he’s an earnest man in a difficult job.

“This is a President who has used the expression ‘Not a joke, folks’ more than he has told actual jokes,” said Jeff Nussbaum, who until this week worked as a speechwriter at the White House and has been involved in humor speech preparation for Biden. “That’s not necessarily a bad thing in serious times. It’s just that President Biden is a serious person dealing with serious challenges.”

Biden’s speech has been in the works for a few weeks, officials said, and wasn’t finished as of Friday. But at the outset of the writing process, the President told his team he envisioned an address that went beyond just an amalgamation of one-liners, wisecracks and gags.

Yes, there will be jokes – about himself, about the media and about Republicans – that Biden is currently refining from a list of dozens submitted by his wide orbit of advisers. But he also intends to use the appearance to loudly affirm his belief in a free press after his predecessor – who skipped the yearly dinner – labeled reporters the “enemy of the people.”

“Think of what the American press has done,” Biden said this week in a speech about Ukraine, mentioning the upcoming dinner as a moment to celebrate reporters. “The courage it’s taken to stay in those war zones. … I can’t tell you how much respect I have, watching them in these zones, under fire, risking their lives, to make sure the world gets the truth.”

“He has made the decision he wants to attend, in a safe way, the White House Correspondents’ Dinner to show his support, showcase his support for the free press,” Psaki said this week. “That does stand in stark contrast to his predecessor, who not only questioned the legitimacy of the press on a nearly daily basis, but also never attended the dinner.”

A tough time for jokes in front of a tough crowd

Like any comedian, Biden has weighed his audience and the current environment as he determines what to say.

Now is not the easiest moment for topical stand-up, officials acknowledge. There is nothing funny about the war in Ukraine or its atrocities. And while the Covid pandemic and its myriad interruptions to life have provided plenty of fodder for comedians, its death toll and economic ripples are not topics anyone can laugh about.

“It is a challenge for the people writing this speech that there’s so many serious issues going on in the world. At the same time, I think it’s important that the President is doing it. President Trump never showed up to this dinner because he couldn’t stand the idea of being made fun of and they don’t know that he would have done very well,” said Litt, who led a process of drafting President Barack Obama’s annual comedy speeches at the correspondents dinner.

“Having a president come up and be able to make fun of himself, generally tell some jokes, talk about the press and maybe make fun of the press a little bit, but also talk about the role of the free press – these aren’t small things, they’re big things.”

The pandemic will be hard to ignore at the dinner, attended by more than 2,500 people in a basement hotel ballroom. At least one high-profile attendee – Dr. Anthony Fauci, Biden’s chief medical adviser – has decided he won’t go. And Biden’s team has taken special precautions to avoid him getting infected, including only attending during speeches and not the part when people are eating.

But he remains intent on being there, Psaki said this week, to demonstrate his support for a free press. Before the big night, Biden is expected to do a few practice runs of his speech to get a feel for the delivery and timing, a person familiar with the matter said.

“Comedy requires rhythm and timing that might not be as natural within the context of a normal speech that he’s given 1,000 times as a politician,” said Matt Teper, who worked as speechwriter for Biden when he was vice president. “He has a natural sense of humor, and he cared enough to make sure that came through almost professionally and in a polished joke telling kind of way.”

Flopping at a dinner for Washington insiders is hardly one of Biden’s primary concerns in these grave times. Still, delivering a speech that draws some laughs and needles just the right amount is not a task the President or his team are taking lightly.

“I do not envy him for having to deliver it. I do not envy the people who are writing it around him and the people who are even writing the jokes with? All of this pressure bearing down on every word,” said Teper.

Washington Funny, Actual Funny and what a President can say

A White House official said Biden’s top speechwriter, Vinay Reddy, and his senior adviser, Mike Donilon, were putting together the President’s remarks. They are working from “a wide submission of jokes from a wide array of folks internal and external,” the official said, following a well-established routine for presidential comedy writing.

As of the middle of this week, Biden had been presented a long list of jokes, from which he’ll pick and choose his favorites. Officials said the chief of staff Ron Klain, members of the communications team and others inside the White House sent jokes to Biden’s speechwriters for consideration. Rob Flaherty, the director of digital strategy, and Dan Cluchey, a senior speechwriter – both said to be among Biden’s funniest staffers – have been sending material.

When he was president, Obama brought on comedy writers from Los Angeles and New York to provide input for his speechwriting team with the yearly correspondents’ dinner speeches — including producer Judd Apatow and writers for “The Daily Show” and “30 Rock.”

Biden, when he was vice president, also sought outside help for comedy speeches he delivered at the yearly Gridiron dinner and in other lighthearted settings.

Among those Biden has turned to was Jon Macks, a top writer on “The Tonight Show with Jay Leno” who has also written host material for dozens of Oscars ceremonies, along with an extended constellation of acquaintances. One person involved in the process when Biden was vice president recalled a submission from Seth Meyers, then the head writer on “Saturday Night Live.”

The trick, according to people involved in the process for Obama and Biden, was whittling down a list of hundreds of jokes into one coherent speech that sounded natural coming out of the president’s mouth. Jokes that may have killed on a late-night show or in a comedy club could sound stilted or contrived coming from a president.

Crude humor, even when delivered artfully, is usually beneath the office – as Obama’s writers discovered when he rejected a gag alluding to his penis size, though he did laugh loudly at it. And insults about physical appearance are generally a no-go in official Washington.

“The challenge with this speech for a president is always to find that little area of overlap between Washington Funny and Actual Funny,” said Nussbaum, who also worked on some of Obama’s correspondents’ dinner speeches. “There’s one circle that’s Washington Funny, there’s one circle that’s Actual Funny, and then there’s a third circle, which is what can a president say?

He added, “A comedian can joke about Covid, a comedian can joke about Putin and Ukraine. A president really can’t.”

Potentially easiest for Biden is the self-effacing style he’s used in the past, including in his video appearances at correspondents’ dinners past. Yet even that comes with potential risk.

“President Biden has a challenge because self-deprecation about his age or his sharpness runs the risk of confirming the, let’s call it malarkey, his political opponents are trying to push,” Nussbaum said.

Searching for politically appropriate humor in 2022

For almost a century, presidents have been showing up to the annual dinner for White House correspondents, which was described in 1922 as “an occasion of much gayety and enthusiasm.” According to one attendee of the dinner a year earlier, the evening provided “such fun as the Prohibition Era afforded.”

When Calvin Coolidge became the first president to attend the dinner in 1924, he didn’t deliver a comedy routine. That tradition didn’t come until later, when presidents discovered comedy presented them an opportunity to obliquely talk about things they’d otherwise been avoiding.

“One of the ways these speeches have functioned historically is that you can talk about things without talking about them. Humor gives you the ability to shift the burden to the audience to come up with the joke,” said Don Waisanen, a professor of communication at Baruch College, City University of New York, who has studied White House Correspondents’ Dinner speeches dating back to Coolidge.

President Bill Clinton utilized the technique in 1999 when making a sly reference to to his affair with White House intern Monica Lewinsky, alluding to the “events of last year” without actually discussing his impeachment proceedings.

Less successful was President George W. Bush’s comedic slide show about searching for weapons of mass destruction at the 2004 Radio and Television Correspondents’ Dinner – a gag that fell flat and led to accusations he’d crossed a line.

Biden’s speechwriters and aides are working to ensure that doesn’t happen this year. And Biden himself has told some on his team that certain jokes either don’t work, go too far or don’t really sound like him.

But in a hyper-polarized political environment – arguably far uglier than in 2016, the last time a president delivered a speech at the correspondents’ dinner – whether Biden can say anything truly, universally funny remains an open question.

“I actually think the most interesting thing about what’s going to happen here is that this speech is going to be a real test case for what is comedy in the US in 2022,” Waisanen said. “It used to serve as: Let’s find some humanity here, let’s find the lighthearted. In 2022, things are so partisan and so tribal, is there anything beyond the most pointed partisan humor?”