Updated April 25, 2023 at 4:02 PM ET
Roy Wood Jr. was having a moment.
When I visited him at The Daily Show's studios in midtown Manhattan — just as he was about to begin his second night guest hosting the program — the comedy gods had brought serious gifts.
Donald Trump was arrested and arraigned that afternoon (Wood cracked that Trump looked "like someone told him his dog died or Mike Pence was still alive"). Correspondent Jordan Klepper had juicy footage of his confrontation outside the courthouse with perpetually untruthful Congressman George Santos, and a certain former host stopped by to say hi — for the first time since his predecessor, Trevor Noah, had left the show last year.
"I used to work here when the budget wasn't as big," Jon Stewart joked, looking around at the expansive studio ringed by banks of video screens centered on a large, sleek-looking desk. "You're doing a fabulous job, by the way."
Sitting in his office after the show ended, Wood admitted Stewart's visit – which he learned would occur just the night before — felt like a stamp of approval.
"It was a little weird being with him in the writers' room," Wood admitted, laughing a little. "Like, trying to suggest lines to Jon Stewart? [He says] 'Right here, should I say this?' [I say], 'You Jon Stewart, say what you want.' "
Wood's also having a moment career-wise, and not just because he got to guest host the show where he's been a correspondent for more than seven years. On Saturday, he'll be the featured entertainer at the White House Correspondents' Dinner, offering a tart monologue on politics and media which will be broadcast to audiences worldwide in one of his highest-profile appearances yet.
It's a long way from his early days in stand-up, where he rode the bus to shows before he owned a car.
Experiencing what a host really does
Wood's blustery stage persona can mask how thoughtful and deliberate he is off-camera, especially when crafting jokes. In the guest host's chair, he's experienced the difference between what a correspondent does and what the host does.
"The host gets to have feelings," he said. "You have an opportunity to sprinkle a little bit of humanity into what you're talking about. ... I can talk about when I was 19 and I stole a credit card. So I know what it's like to be in a courtroom alone with no friends. Trump's face is exactly someone who goes, 'Wow ... I didn't think today would come.' "
Wood seems a strong contender to nab The Daily Show host's chair permanently, as he's being hailed by fans on social media and name checked by luminaries like Late Show host and Daily Show alum Stephen Colbert.
According to figures from Nielsen and Comedy Central, the TV ratings agree. Wood had the second most-watched week among the first 11 guest hosts — the numbers don't include recent stints by Jordan Klepper and Desi Lydic — only Al Franken did better. Wood says if Comedy Central and the powers that be offer him the gig, he'll take it ("I don't think you can say no to an opportunity like that.")
But Jennifer Flanz, executive producer and showrunner for The Daily Show, wouldn't talk about Wood's chances of getting the job, even when I asked her directly — while referencing that old saying about parents loving all their children equally.
"There are four kids in my family and my parents used to say it to us, and I never believed them," Flanz said, laughing. "This is the first time I've [thought], actually, I get it. You do. You love all your children the same. They're all so talented."
Turns out, Stewart appeared on the show with Wood because Flanz asked him. She says they talked after news broke last year that Noah was leaving the show, and Stewart asked what he could do to help.
"We saved that up for our own news team," she added. "Roy was the first of our news team to go, and it seemed like that was the most appropriate time."
Recalling how intensely Noah was compared to Stewart early on, Flanz said she pitched the notion of rotating guest hosts to create some distance between the new host and the last host. The hope: to remind audiences that The Daily Show is an institution with an identity and influence beyond any single host.
Flanz hasn't even decided if she thinks the show should have one permanent host, anymore.
"I wanna work with everyone and then decide what the next best phase of The Daily Show is," she added. "Are we evolving the brand in any way? Is it one voice ... is it multiple voices? Are we in a time when people just want to hear from one person all the time? I'm not sure."
Stepping into a role that suits him
Still, there's someone else who thinks Wood would be perfect as a permanent host of The Daily Show – the guy who last had the job, Trevor Noah, himself.
"I can't think of anyone more deserving both in talent and character to host the show than Roy Wood Jr.," Noah said, speaking by cellphone on his way to headline a stand-up comedy concert in Boston. "Roy ... he hasn't stepped up, I think he's stepped in to a position and role that really suits him. It's one of those instances where the world has to catch up to his talents."
Wood was among the first correspondents Noah hired when he succeeded Stewart in 2015, saying no one thinks quite like he does.
Among Wood's greatest early hits: talking with Noah for a "report" on this possibility of Black folks living on Mars, saying, "brother can't catch a cab, you think we can catch a spaceship?" Or a bit with Klepper where he asked the police chief in Madison, Wis., if officers are biased, shouting "Got 'em!" when the chief answered yes.
Another great example: a moment from his 2017 stand-up special Father Figure, where Wood takes a sentiment you might expect him to agree with — that the Confederate flag should be banned — and turns it on its head.
"If we get rid of the Confederate flag ... how am I going to know who the dangerous white people are?" he asked, to roars of applause from the crowd. "You stopping for gas at a strange place at 2:00 in the morning, you see that flag hanging from the window, you know this is not the place to get gas."
Noah says the key is finding a way to make everyone laugh: "It's really difficult to step into any space that requires some sort of insight, find a way to process your thoughts, but also find a way to not alienate anyone in the audience, while still being honest and authentic. And I think that's what Roy is really good at doing."
That instinct comes from Wood's earliest beginnings in comedy, 25 years ago while studying broadcast journalism at Florida A&M University. His father, Roy Wood Sr., was a pioneering radio journalist who covered the civil rights movement. But the younger Wood wanted a different path.
He's honest about a moment that almost derailed his life; while in college at age 19, he stole a credit card and used it to buy some jeans (Wood jokes now that he got caught so fast, he didn't even have time to wear them.)
He got suspended from college — but it was after his financial aid check came in. So he used the money to go on the road as a comic, taking the bus to far flung comedy clubs. By the time he graduated and moved back to his hometown of Birmingham, Ala., he was regularly working stages from Orlando to Wichita, driving back home in time to appear on a morning radio show.
"Find me the joke that makes all of those people laugh, that's a good joke," he said. "So when you sit down in the chair at The Daily Show, who are you entertaining, college kids, retirees, regular middle class? It's all the same people that I went from Oklahoma to Sioux Falls entertaining for the better part of a decade."
Saving the late night talk show genre
The late night talk show genre has reached something of a turning point, with stars like Noah and James Corden leaving the space even as ratings decline and social media monopolizes the attention of young viewers who once showed up for David Letterman and Conan O'Brien.
But Flanz says audiences need what programs like The Daily Show provide.
"We're heading into an election year ... and having late night shows in general in this country is important," added the executive producer, who has worked at The Daily Show since its first host, Craig Kilborn, was on the job. "We are very lucky to live somewhere you can say whatever you want about the leadership ... and laugh about things that might be scary. I think that it would be a huge mistake to not revive late night if people think it's dying."
Wood wonders if they should move beyond parodying traditional newscasts, where fewer and fewer people actually get their news. He also wants to find space to feature the opinions of average people.
But he hates the idea of keeping guest hosts on the show permanently, like Saturday Night Live.
"SNL is a show that's led by the cast ... the cast is the star," Wood said. "The Daily Show is a [program] that's run by the host. ... If there is a mass shooting tomorrow, we have to talk about it. And I'm not sure if having a guest host in that particular week, is the strongest possible choice for offering catharsis to the viewers."
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