It Took ‘The Daily Show’s’ Roy Wood Jr. 20 Years to Get This Good

AUSTIN, Texas — When Roy Wood Jr. comes down to meet me in the lobby of his hotel early on a Sunday morning in Austin, he’s wearing a faded yellow Ric Flair T-shirt and a crisp Cubs hat. South by Southwest—and the rest of the country—lost an hour to daylight saving time the night before and the lack of sleep shows.

But the 39-year-old stand-up comedian and Daily Show correspondent wasn’t out late partying the night before. He was in his hotel room with his girlfriend taking care of their baby son.

“I don’t like festivals,” he tells me in the elevator ride up to the JW Marriott’s private breakfast lounge. “There’s so much shit going on.” We pass his friend Amber Ruffin, a writer and performer who works on Late Night with Seth Meyers, in the hallway, but they’re both too busy to say more than a quick hello.

Over some morning beverages—coffee for me, cranberry juice for Wood—we talk about how he’s arrived at the height of his professional success exactly 20 years after he started performing stand-up at small clubs in his home state of Alabama.

In addition to his regular gig on The Daily Show, Wood hosted the recent fourth season of Comedy Central’s stand-up showcase This Is Not Happening and has yet another series in the works with the network that he’s co-creating with The Boondocks’ Aaron McGruder called Re-Established.

Wood started on The Daily Show the same night as Trevor Noah in September 2015. Before that, he was a regular on the TBS sitcom Sullivan and Son as served as a comedic correspondent of sorts for ESPN. He credits the appearances on ESPN’s SportsNation with landing him the Daily Show gig.

In the two and a half years since he made his debut on the show, Wood says he’s watched Noah really come into his own as a host. He compares the South African-born comedian to Black Panther, taking the audience’s energy and firing it back at them.

“Trevor has a unique way of absorbing the energy and the zeitgeist and matching that in his delivery,” he says. He remembers the “visceral” feeling on set during their live election night show when it became clear that Trump was going to win. He admires the way Noah was able to read the situation and react with the appropriate gravity.

“Where delivery’s concerned, I feel like I’m one note, maybe two notes,” he says. “Trevor’s like 40.” Wood considers his two notes to be “frustrated” and “confused.”

“I think the show has found its voice in terms of finding the most unique take on an issue,” he says, noting that Jon Stewart never faced as much competition. In an already overcrowded field, Netflix has announced just in the past few weeks new late-night-style shows from Daily Show alums Michelle Wolf and Hasan Minhaj, as well as another from Norm Macdonald and potentially even a new series hosted by former President Barack Obama.

“Obama needs to go somewhere and windsurf,” Wood jokes about the latest competition. “C’mon, Obama, what are you doing?”

Instead of taking the talk show path laid out by former colleagues like Wolf, Minhaj, Jordan Klepper, and others, Wood has decided go a different way. There was some talk about him hosting a sports-themed late-night show for Comedy Central, but he was worried that he wouldn’t be able to make fun of the sports world and still “have access” to athletes and leagues who tend to “take themselves too seriously.”

He describes Re-Established, which will shoot its pilot later this year, as “a buddy comedy” about two probation officers. “Ultimately, the goal with the show is to put a face to the people that are getting a second chance in life,” he says. “When you look at our criminal justice system and the recidivism rate, I think there’s something to be illustrated about the journey from being arrested to so-called normalcy.

“It’s not typical television fare,” he acknowledges, “but I think the good stuff rarely is.”

Wood is in Austin to perform stand-up as part of SXSW’s comedy festival. And in a headlining spot at Esther’s Follies on Sunday night, he displayed masterful control over the audience during a 25-minute set that covered everything from McDonald’s “real chicken” McNuggets to what The Shape of Water taught him about catcalling.

“I’ll tell you what’s the same: Write the joke, perform the joke, hone the joke,” he says of his two decades performing on stage. “What’s different is that the doors to entry in comedy change often.” When he was coming up, he says, the key was getting TV credits. For Wood, that meant appearances on shows like Star Search and Premium Blend in the early 2000s.

Now, he sees young comedians skipping that step altogether and uploading material directly to YouTube or Twitter. Where Wood had to rent a video camera from Rent-A-Center and then dub the tape to VHS to review his own stand-up sets, younger comics can do the same with their phones.

“I should have taken the internet more seriously,” he says of his early days in comedy. “One of my biggest regrets in my career was ignoring the changing tides and listening to bitter, older road comics who dismissed change.”

Among those road comics he looked up to were Paul Mooney, Ron White, and Doug Stanhope. “I’ve never seen anyone living their truth better than Stanhope,” he says. Wood admits that he was pretty much a “Martin Lawrence impersonator” when he started out.

As for the way America’s heightened political correctness has affected his material over those 20 years, he says he tries not to let it bother him. “If I make a joke you don’t like, I’m OK with that,” he says. “People have a right to be offended. Comedians are being unrealistic if they think someone can’t be offended. You as a comedian can then decide to not give a shit if they are offended.

“Comedians are always the tip of the sword of change,” Wood adds. With that comes some “growing pains.”

“The thing that’s unfortunate is that the people who know are quick to attack the people who don’t know, as if they should have known,” he explains. “But everything you know at some point was taught to you.”

He cites the evolution from LGBT to LGBTQ to LGBTQIA as an example. “It takes time to learn that,” he says, “so if you forget to put the ‘IA’ on and someone jumps down your throat and calls you a piece of shit, I can’t be mad at them. I just consider myself educated.”

Toward the end of his SXSW set, Wood delivered a bit about how Hugh Hefner “died right on time,” before his career could be sullied by the #MeToo movement. The Playboy founder passed away at the end of September 2017, about one week before the Harvey Weinstein story broke. 

“Nobody timed their death more perfectly than Hugh Hefner,” he said. Wood speculated that Hefner knew a “Weinstein-level exposé” was about to come out about him and “like a fucking boss, he talked it over with his team, said, ‘I’m out this bitch, Wakanda Forever!’”

When the applause died down, Wood said quietly, “This is the moment in the set when I should have left.” But he just couldn’t help himself, and did another five minutes.