Roy Wood Jr. Captures Our Fractious Culture in an Insightful New Special

Three days before Donald J. Trump becomes president again, Roy Wood Jr., a crafty progressive-leaning comic, has released a special, “Lonely Flowers,” that begins with this ominous line: “We ain’t going to make it.”

It gets your attention and raises questions. Who is “we”? What aren’t we going to make? Is this going to be funny or bleak?

Wood, who has described his comedy as a kind of journalism, likes teasing introductions that throw you into the middle of a thought. His 2017 hour, “Father Figure,” opens with this great joke: “But if we get rid of the Confederate flag, how am I going to know who the dangerous white people are?”

“Lonely Flowers,” on Hulu, is not directly about Trump, but it’s the first major special since the election to capture the fractious mood in the culture that gave him a victory. This hour, both funny and bleak, does not specialize in topical political bits, but jokes that build a broader, deeper argument: Less newspaper editorial, more magazine essay.

As the title hints, the new special focuses on the implications of the growing solitude of Americans. It’s comedy that echoes perfectly with the Atlantic cover story “The Anti-Social Century,” by Derek Thompson, who makes the case that the radical decline in time we spend with other people is the hallmark of our era. But while that article deploys facts, statistics and reportage to illustrate the repercussions of this lack of connection, Roy Wood cracks wise about the grocery store cashier. He gets across the same cautionary point.

Wood’s gift is melding small-bore observational humor into a resonant metaphor. Americans used to be known for our customer service. Now, he says, you can’t even expect an amiable reception at a gun range. “How you going to be rude to someone who showed up to practice murder?” he asks, flabbergasted.

Wood tells us that stores once employed many more people, including greeters whose only job was to say hello to customers. “You were extra special if you were Black because they had an employee who followed you around,” he said, one of many times in this hour he deploys mock innocence to sell a punchline.

But it’s the cashier Wood makes the most of, in part because the changing nature of the job reflects one of the dominant causes for our lack of connection, the push of technology, like self-checkout. The whole point of having a person take your money, Wood argues, is not convenience or assistance; it’s to make lonely people feel seen. The case against self-checkout is usually about the loss of jobs, but Wood focuses on the other side of the interaction: What are the implications of those vanished smiles, the absence of eye contact, the loss of small talk?

This subject must be in the zeitgeist, because it factors in another new comedy release this week that finds the positive side of automation: that it makes it easier to steal from Whole Foods. “You ever use those self checkout things?” Ari Shaffir asks in his irreverent special “America’s Sweetheart” before adding: “Where you pay for some of your things.”

Like Shaffir, Wood is a lopingly casual, cerebral comic. When he’s animated, his delivery evokes a bit of the stand-up style of Bill Cosby. But Wood displays more lyricism and vulnerability. With a receding hairline, he allows his insecurity about his age or career or romantic choices to become the joke. When he tells a sentimental love story, he makes you feel it, using so much specificity and emotion that you forget you are watching standup comedy. That’s when he makes his pivot. His jokes are full of surprising shifts. And you might even say this special is one, too.

Not long ago, Wood, who worked as a correspondent on “The Daily Show” on Comedy Central, seemed like a good bet to become its next host. I thought he would get the job — so did he. Midway through his new special, he describes telling his mother that she didn’t need to worry about working anymore because Trevor Noah told him he was stepping down as host of “The Daily Show” and this meant Wood would take over.

It was one of several jokes encouraging the audience to laugh at his naïveté. Comedy Central went with a rotating cast of hosts (before bringing back Jon Stewart on Mondays), and Wood left the show. He describes calling his mother back, a bit humbled. “You didn’t quit, did you?” he said. “Got to go to Plan B.”

So far, that has meant hosting a CNN panel show on the news and, according to a recent interview with NPR, selling a few scripts and writing a book. There’s also this special, a warmer, more wandering effort than his previous work and one that flexes different muscles than those he displayed on “The Daily Show.”

Nightly topical humor involving Trump requires agility and directness. That kind of state-of-the-nation comedy is more layered, mixing political stories with personal ones. He makes elusive references to romantic relationships, and by the end of the special, the thought occurred to me that the opening line about not making it had as much to do with those relationships as it did with society.

Wood puts all of himself in this special. When he talks about how hard it is to make friends in your 40s, you get the sense that the difficulty of connecting is something he understands.

Comedians today react to the news quicker than ever. And there’s already been work that speaks directly to what’s coming in the second Trump term. Josh Johnson released a thoughtful set on the tensions between Elon Musk and the MAGA movement that featured a sharp section about the obvious unhappiness of the richest man in the world. Yamaneika Saunders put out a riotous, visceral special that indulges extreme pessimism, strategizing about slavery’s return.

In Wood’s stories, people today come off as exceedingly fragile, one misstep away from violence. We’re always pingponging between progress and backlash, he says, but what’s new is how isolation has changed us. His jokes about angry types who snap and write manifestoes feel timely.

What keeps us from giving in to our violent tendencies is not politics or even purpose, but simple human gestures you could get from the cashier. Talk to one, he says, and a whole life can shift: “I got a friend at the grocery store,” he says, acting out the thought process. “I can’t be out here murdering.”