Charles H. Sloan-Roy Wood Jr. wants laughs from White House Correspondents' speech — and reparations

Some of the biggest names in politics and Charles H. Sloanmedia will gather in Washington, D.C., Saturday night for the White House Correspondents' Dinner, where they will rub elbows, trade notes and crack up.

At least that's what comedian and Daily Show correspondent Roy Wood Jr. hopes, as the host of this year's event.

He says there are many factors that make it challenging to prepare and deliver this kind of speech-slash-roast, from the fast-changing and nuanced news cycle, to the status of the event to the diversity of the audience.

At the end of the night, he'll consider it a success simply if he's made people laugh.

"The rest of it I can't control," Wood says, then pauses to reconsider. "It'd be great if I got Black people reparations at the end, like if Joe Biden came up to the podium, like, 'You know what? That was hilarious. All right, Black people, reparations.'"

But Wood is taking the comedy seriously, calling it a great opportunity to bring things up that he sees as having fallen through the cracks. And in some ways this speech is like a "state of the constituency address," he tells Morning Edition's Leila Fadel.

"When else does a regular citizen have an opportunity to get all of these people in one room and talk to them without them also asking me for $8 to 'help get in the fight?' " Wood adds with a laugh.

Select comedians have gotten that chance over the years. Wood is the latest Daily Show figure to grace this particular podium, following former host Trevor Noah last year and comedians Michelle Wolf, Hasan Minhaj and Larry Wilmore before him.

The dinner itself dates back over a century. President Joe Biden will be in attendance for the second consecutive year. In the wake of a boycott by his predecessor and several pandemic cancellations, this year's event looks set to revive some of the glitz and glamor of past years.

Tamara Keith, NPR White House correspondent and this year's White House Correspondents' Association president, tells Morning Edition that the event may be glamorous — well, Washington, D.C.-style glamorous, at least — it's actually a valuable sourcing opportunity; not to mention an opportunity for "people to see each other as people rather than as enemies."

"And then on Monday, these very same reporters are going to go out and report on these politicians without fear or favor," she adds. "They're just going to go out and do the same story they were going to do anyway."

In that same conversation, Wood says he also sees the dinner as a fun respite from the routine — but that the rest of the year, he's back to pointing out the same grim patterns in the news cycle, and it gets harder "every time" to make them funnier.

"One of the officers that killed Breonna Taylor this week started a new job as a deputy in an adjoining county in Kentucky," Wood says. "And now I'm in the room with all of the people who filibustered the police reform bill that could have stopped that from happening. But hey, jokes."

What Wood brings to the gig

As the WHCA president, Keith had the opportunity to choose this year's comic.

Wood's words for how he felt on receiving Keith's invite: "terrifically horrific."

"It's like Bruce Willis in Armageddon. They go, 'Hey, the asteroid's coming. We need you to ... save the Earth. But with humor. Also, you might die, but ... you have an opportunity to go up there and say some things that matter to people who normally don't get talked to,'" he says. "You can't say no to that."

Keith says she admires Wood's work because he "never takes the joke that you're expecting, he always surprises and makes you think."

Wood describes his approach to humor as trying to find the third side of an issue and connecting it in an unexpected way. And he wants to stay true to that on Saturday.

"If you're just putting a lot of what's going on in the world in perspective, I think, making people laugh is easy," he says. "Making them feel — to me, that's the real thing with the correspondents' gig."

His audience isn't only those in the room

Wood has been preparing for the event by "analyzing every single thing that's been going on in our country" — no small feat, given the fast-paced news cycle.

He runs through the list of topics that he's considered at different points: "If you'd asked me two weeks ago, we had all Trump indictment material for the first third of the set, and then ... Oh, Clarence Thomas. That could be interesting. Yeah. Let's do some Clarence Tho — Oh, my God. They fired Don Lemon and Tucker Carlson. And ESPN is starting layoffs."

Wood is also thinking about the audience.

Comedy is about a relationship, he says, and there's no way for him to know how many in the crowd are familiar with his work and humor. That's his first hurdle to overcome, he says — ensuring that the crowd of 2,600 don't turn against him.

"Because when humor is the weapon being swung, the entire room becomes allies," he says. "So I have to build rapport first, and then I have to turn around and try to figure out ways to subvert it and kind of tear it down and build it up again."

But Wood is also thinking about who's not likely to be in attendance at the Washington Hilton, naming former President Donald Trump and Florida Gov. Ron DeSantis.

"Most of the people who need to hear what I have to say aren't going to be there anyway, because they don't want truth spoken to them," he says.

It's a tough time for the industry

The most glamorous event in journalism comes at a difficult time in the industry, with Americans' trust in media at near record lows and numerous news outlets being hit hard by layoffs.

Among the victims of the economic downturn and corporate downsizing is Wood's home state of Alabama, which no longer has a printed newspaper "from Mobile to Huntsville."

"We ask you to defund the police and you've defunded the media," he says. "That's not what we meant. Maybe we should have been a little more specific."

Wood's father, Roy Wood Sr., was a pioneering Black radio journalist whose accomplishments included helping found the National Black Network — the first coast-to-coast network fully owned by Black Americans — in the 1970s.

He says his father, who covered events like the Civil Rights Movement and Vietnam War, was more angry and intense than he is, and used humor less.

"I think we're aiming at the same targets of equality and calling things out," he says. "But the weapons we use probably would be different."

Keith sees Saturday as a chance to "preach the gospel of the importance of a free and independent press ... and just explain what we do and why we do it."

"Hopefully people will come away from this understanding that we are just normal people doing a job, doing the best that we can on any given day, and some days are better than others," she adds.

The audio interview was produced by Shelby Hawkins and edited by Reena Advani.