Before he headlined the White House Correspondents’ Association dinner, Roy Wood Jr solicited advice from Hasan Minhaj, Michelle Wolf and other Daily Show alums who have landed the gig. They all told him the same thing: don’t have any regrets. But more than a week after his 25-minute set, Wood is still grappling with a bridge bit he did on mass shootings. “Drag queens are not at the school to groom your kids,” he intoned three minutes in. “And even if they were, most of them kids [are] going to get shot at school; it ain’t no problem.”
As groans filled the air, he further prodded the lawmakers in the room to “pass legislation” if they couldn’t take his joke – ca callback to Barack Obama’s “don’t boo, vote”. The joke sparked even stronger backlash outside the room, with many dismissing Wood as the most insensitive agent of wokeness yet. That it was followed by another mass shooting in Texas days later didn’t help – but it certainly made his point. “There are always going to be people who will use any opportunity to misconstrue a joke for political points, which some people are doing with that joke online,” he tells me, a little defensively, over the phone.
Wood now finds himself at a career crossroads. His years grinding as a standup comic earned him steady work as a Daily Show correspondent – he joined the program in 2015, at the start of Trevor Noah’s tenure. Now, the 44-year-old is angling to take over hosting duties.
Despite his immense popularity, Wood faces significant headwinds. Non-white representation on late night is about as bad as it was 20 years ago. Wood might also not be considered a flashy choice for one of Paramount Global’s flagship properties.
While The Daily Show was on pause in solidarity with the writers’ strike, we considered that punchline, Biden and Trump’s appeal with Black voters and whether he was serious about walking away from The Daily Show if he doesn’t land the big promotion.
How was the correspondents’ dinner different from other gigs you’ve done?
It’s not like a rap concert, where if you talk trash about a rapper, his crew is gonna be waiting backstage to beat your ass. No one was walking around looking for me like Chris Brown after an Usher event. It was politics. Maybe I’ll get audited. At least Kellyanne Conway thought I was funny.
Do you feel like you said everything you wanted to?
I think my set showed that I can get people on the other side of the aisle to at least laugh. And if I can get you to laugh, I can get you to listen. So maybe the next time around, I’ll get to say something a little bit more poignant. Or something with a bit more teeth to it, if you will.
What was the joke you kept thinking about after you did it?
I was probably most nervous about the Kamala Harris joke. It was about how sexism plays into critical assessments of her job performance and I was concerned it would be misunderstood. [“If a VP’s job is really just waiting to step in to save the country in case of emergency, then the job of vice-president is a perfect job for a Black woman,” went the joke. “Whatever you do accomplish, whatever you do accomplish, all they going to do is just give a man credit for it.”] I knew the school shooting joke was going to elicit groans too but I refuse to say I shouldn’t have done it.
I don’t feel like everybody has the same comedy IQ anyway. That’s really what a lot of the outrage toward me boils down to. Some people just aren’t bright enough for my type of program.
You’ve referred to your first decade in a comedy, where you spent lots of time playing comedy clubs in the south, as a “very bitter education on the psyche of the middle of the country”. What did you learn?
You learn, real fast, what connects people. These different demographics I’m performing for every night may not know me or want to hear me, but it’s still my job to bring the room together. Some nights, I’ve had people tell me: “I thought you were funny, but don’t leave the hotel tonight. It’s not safe.” Not a common occurrence, but it has occurred.
But I’ve also had nights where I’m standing on a street corner in Appleton, Wisconsin, eating a burrito outside a bar at one in the morning with a whole bunch of cool people I just met. No doubt there’s racism and inequality in America. But on a base, person-to-person level, we’re not nearly as divided as we’re made out to be.
Does that mean America is ready for a southern-fried, Black Daily Show host? Will there still be viewers too paranoid to invite you into their homes late at night?
If somebody’s trying to decide whether to watch me solely for my skin color, they’re probably not the right viewer anyway. Larry Wilmore had a show for a while, and people invited him in. Trevor was invited in. Charlamagne tha God has had a couple of tries hosting late night shows at Comedy Central. I don’t feel like what I’m doing is completely unprecedented. To have an opportunity as a Black American to just talk about issues from my perspective, it’s gold. But I think they’ll eventually realize that I’m mainly in it for the jokes, not to preach.
What makes you think you’re ready for the big promotion?
I just think that if you’re doing something interesting well enough for long enough that people will eventually catch on. And for the past 25 years, I’ve just been showing up, putting in the work – wash, rinse, repeat. The grind doesn’t stop.
Three nights after the correspondents’ dinner, I was back on stage in New York at the Comedy Cellar working out jokes for my national tour this summer and fall. It’s always back to work with me. I’m literally telling myself, “Get back in the car, fucker.”
What would landing the job mean for your work/life balance?
My son is seven now. Last time I went out on tour he was four. No parent wants to be away from their child for an extended period. That’s why I’m anxious to host something. It’s not just solely about my creativity; it’s also fiscally.
So there’s part of me that looks at the job for what it could mean to me for my ability to provide while also being home a lot more. I don’t want to spend 45 weeks on the road every year if I don’t have to. Going out in a nice wave every two to three years would be the ideal approach.
I’m guessing the writers’ strike probably has you home a bit more these days. What’s your take on it?
We’re shut down like everyone else in the city, and for a good reason. This is an important battle in terms of pay equity and monitoring the evolution of technology.
AI, you mean.
The concern is fair.
As a prolific contributor to Black Twitter, are you at all troubled by the rise of digital blackface? Last year Capitol records tried to launch an AI Black rapper.
Thankfully, that is one of its glaring limitations right now. AI has got to be programmed by somebody, and we all know tech companies don’t have the best record of hiring Black people. So who’s gonna fuckin’ make this shit Blacker?
They’re already kind of doing it, like with that fake Drake song. That was for sure one of those “Hey, do you mind if we try – oh, no, bad idea? Right. Yes. So sorry. So sorry!” moments. They’re testing the waters to see how people respond.
But at some point you’re gonna need the human touch and expertise that comes through lived experiences. That’s why the writers’ strike is so necessary. It also affects the directors, the actors’ guild, animation. It’s not so much a writers’ strike as it is a beachhead across the industry in all positions. The writers are just the first ones on shore.
Back to Biden. Is we is or is we ain’t voting for him? Did he offer up any more threats if Black voters don’t go with him again in this election cycle?
I didn’t see anybody after [the correspondents’ dinner]. Not Biden or anyone from Fox News or even from Clarence Thomas’s camp. That said, I haven’t had a chance to really look at his policy points. But I think Democrats would be wise not to run a platform under the assumption that the Black vote is already a given. It’s not.
Trump looks likely to be the Republican nominee again, but it’s been a long time since rappers were name-checking him in the 90s. Does he have any standing with Black America?
How many references are being made in rap songs today? Not many. He doesn’t have that same cool cachet as he did before with the Black community. What’s more, Trump being cool versus Trump being electable are two different things, especially to Black voters. But there are always going to be people who see him as the better option no matter what, even with the indictment.
And what about Ron DeSantis?
He’s clearly trying to activate voters with extremist legislation. But he doesn’t realize that most people who are activated by bullshit laws can only follow one or two at a time. They’re called single-issue voters for a reason. Slow down, my man.
Why is it so important to have you among the late night hosts calling this out?
It’s not often you see a Black host on late night. And when you do, they’re on cable.
Clearly Arsenio set an impossible standard.
I think we have to accept there’s never gonna be another. He was Black America, Black Twitter. He was everything cool all rolled into one burrito.
I will tell you right now: one of the most impactful talkshows out there right now is the [online, live comedy show] 85 South Show, and it’s every bit as meaningful and pertinent to Black culture as Arsenio was back in 1994.
But overall, after seeing some strides toward inclusion on late night, I’m looking at Ziwe being canceled, Desus & Mero being gone, Sam Jay’s Pause being on hold at HBO, TBS canceling Samantha Bee. Amber Ruffin is the last one standing. There’s clearly been a contraction in late night in terms of representation. As far as I can tell, the name of the game is saving money.
Something’s gonna give and, who knows, the writers strike could change a lot. I just know the type of show that I want to do. It would for sure honor who I am and my path, but mainly reflect on and have a dialogue about this country.
And if you don’t get the gig, do you intend to make good on the promise you made in a New York Magazine interview to leave the show completely?
I don’t think it’s so much of a cut and dry “if they don’t hire me, I’m out”. It’s more like: “What’s the new plan, and is there a place for me that I like that also works for the network?” Would I like to host The Daily Show? Sure. But who knows which way they’re gonna go.
You’ve read the rumors, bro. One minute, they’re gonna have guest hosts forever; the next, they’re floating a multiple-chair, Weekend Update-type of situation. I just know that I have a lot to say and need to find a place to say it: whether that’s the stage, a scripted show, something unscripted. It doesn’t even necessarily have to remain within the realm of political satire. Again: I don’t know what Comedy Central wants to do and can’t say that I’d be down for any and everything. But it’s for sure where I’d rather be.
This interview has been edited for brevity and clarity