In the course of this past year, I’ve found myself wondering, more than a few times, whether we are living through the world’s stupidest era. Of course, it’s not as though people haven’t been doing dumb things since the dawn of time. (It wasn’t so smart of the Trojans to let that horse into their city.) But, as the second decade of the twenty-first century proceeded inexorably toward its culmination, it began to seem to me as if human folly—in politics, arts, and culture—was almost willfully outdoing itself. This might not have been strictly, statistically correct—I’m not sure how we might assess if it were. But, with our brains likely rotting inside our skulls as we spend hour after hour scrolling on our phones, and with the Trump Presidency—and all its petty vulgarities and boneheaded indignities—barrelling on, I thought it might make sense to check in and see where we stood. Stupidity, especially in the political sphere, often comes with a side of brutality, and keeping track of it, rather than allowing it to pile on, might help us to hold fast to our higher selves. Also, there is something innately comical about stupidity; if we are forced to suffer fools, we can at least have some laffs in the process. What follows is a non-exhaustive list of some of the major idiocies of the year. If nothing else, it’s been a wild ride.

2019 in Review New Yorker writers reflect

on the year’s best.

In honorary first place comes, naturally, Donald J. Trump. The President has provided enough stellar material to populate several lists on his own. Last week, during a roundtable with small-business owners, Trump meandered off topic and claimed that the E.P.A. was hard at work on solving the dire problem presented by low-flow toilets, which need to be flushed “ten times, fifteen times, as opposed to once.” (Consumer Reports told CBS News that the least efficient models take four or five flushes max.) In September, he falsely maintained that Alabama would be impacted by Hurricane Dorian; during a presentation at the White House, he doubled down by displaying an official National Hurricane Center map in which the state had been clumsily circled for inclusion in the storm’s potential zone, apparently with a Sharpie. In October, after he pulled U.S. troops out of Syria, he wrote a thuggish and ineffective letter to President Recep Tayyip Erdoğan, of Turkey, in which he tried to convince him not to launch a military strike against Kurdish-led forces, and added, “Don’t be a tough guy. Don’t be a fool!” (Erdoğan reportedly threw the letter in the trash before proceeding to invade Syria and attack the Kurds.) What united all of these instances was Trump’s bullheaded refusal to engage with anyone’s reality but his own. This tendency was on full display in what might be the President’s stupidest moment this year. In September, in a chyron, CNN apparently cited a tweet from Trump in which he referred to Representative Adam Schiff as “Liddle’ ”—a form that the network transposed, sans apostrophe, as “Liddle.” Turning once again to Twitter, the President claimed that CNN, as a representative of the “LameStream Media,” “purposely took the hyphen out” of the word he used in “discribing” Schiff. It is, he lamented, “A small but never ending situation with CNN!” What makes this tweet the winner for me is its glorious display of the dense layers of mistakes and misapprehensions that the President labors under. “Describing” is “discribing,” an apostrophe is a hyphen, and “li’l” is “liddle’,” but never “liddle.” (What doesn’t change, however, is Trump’s paranoid sense of persecution.) To read this tweet is to become privy—hilariously, frighteningly—to the thinking process of a man whose head seems packed with cement. It’s a place that even the thinnest rays of wisdom and discernment no longer reach, if they ever did.

The President’s personal lawyer, Rudy Giuliani, also had a strong year, gaffe-wise. His most impressively stupid achievement might have been when he butt-dialled—first in September and then, amazingly, once more, in October—the NBC reporter Rich Schapiro, and left two inadvertent voice mails. In the first call, he spoke with an associate about the Bidens and their alleged misdeeds, and, in the second, he talked about the resources required for his business interests in Bahrain and Turkey. “The problem is, we need some money,” Giuliani says in the second voice mail, in a sound bite that, in its baldness, could have been taken straight from a movie about the hapless mind behind a scam gone wrong. “We need a few hundred thousand.” My colleague Jody Rosen has written that Giuliani, with his accidental calls and Twitter missteps, is emblematic not only of the Trump Administration’s “who cares” strategy of chaos and nihilism but also of our more generally vexed relationship with our devices, whose perennial newness threatens to outpace us. This is indisputably true, and I’ve certainly made typos in texts and uploaded the wrong links to Twitter. I can even (almost) imagine myself wearing Apple AirPods incorrectly, as the attorney seems to have done so memorably in 2018. But there is a special satisfaction in what appears to be Giuliani’s obdurate inability to refrain from this type of behavior. Even the term “butt-dialling” is apt in this respect. It brings to my mind, like a kind of visual poem, the image of a pair of buttocks, in lieu of a head, with an iPhone held up to their nonexistent ear, hearing nothing and yet still, somehow, emitting sound.

And from Giuliani it’s a mere hop and a skip to his associates, the Florida-based, Soviet-born businessmen Lev Parnas and Igor Fruman. The pair, who donated hundreds of thousands of dollars to a pro-Trump super PAC, were arrested while attempting to leave the country in October. They were charged with breaking campaign-finance laws by attempting to mask donations from foreign entities made to U.S. politicians in the hope of influencing U.S.-Ukraine relations. (Both men have pleaded not guilty.) Allegedly, they were also working in Ukraine to dig up dirt on the Bidens, at the behest of Giuliani. This is all, as my colleague John Cassidy pointed out, a “deadly serious matter.” Still, there’s some fun to be had here, especially when thinking about my favorite detail of the whole affair: the names that Parnas and Fruman had chosen for their supposedly legitimate business concerns. In the U.S., Parnas ran a fraud-prevention service that he called Fraud Guarantee. Fruman owned a beach club in Odessa, Ukraine, called Mafia Rave. These names are so frank, so boldly literal (even if unintentionally), I couldn’t help but be a little charmed.

At Game Five of the 2019 N.B.A. Finals, between the Golden State Warriors and the Toronto Raptors, Drake wore a seven-hundred-and-fifty-thousand-dollar Richard Mille watch. Photograph by Gregory Shamus / Getty

Boldness also played a part in another favorite of mine this year. In June, the rapper Drake wore a seven-hundred-and-fifty-thousand-dollar Richard Mille watch, the “69 Tourbillon Erotic,” to an N.B.A. Finals game between the Raptors and the Warriors. The watch’s gargantuan silver-and-black face sports three bars whose displays can be flipped to generate two hundred and sixteen combinations of suggestive phrases. Options such as “I long to,” “I need to,” and “Let me” can combine with verbs, such as “taste” or “arouse,” and, finally, nouns, such as “your lips” or “your nipples.” At the game, Drake’s watch face, as caught by cameras, bore the phrase “I’d love to kiss your pussy.” As these things go, this cut pretty quickly to the chase. At the same time, something about the use of a three-quarters-of-a-million-dollar implement to express this particular desire seemed insanely circuitous. The vaguely corporate language (“I’d love to,” to my mind, works better when preceding, say, the words “pick your brain” or “grab a coffee”) made the whole thing even odder. And whom, exactly, was this message directed toward? Any old person whose eye happened to catch it? The potential for embarrassing misunderstandings here seemed almost too fraught to bear.

Another sort of misunderstanding took place that same month, when Kylie Jenner, the Kardashian scion, threw a birthday party for her friend Stassie Karanikolaou. The theme for the party was Margaret Atwood’s “The Handmaid’s Tale”—specifically, the dystopian novel’s recent TV adaptation, which depicts a theocratic state, Gilead, where, amid dwindling birth rates, fertile women are enslaved as “handmaids” and made to bear the ruling class’s children. In a series of Instagram Stories, Jenner took her followers through the party, which included a red-and-white color scheme, handmaid-regulation red gowns and white bonnets for the guests, and “under his eye” tequila cocktails—for that totalitarian-rape-culture-meets-San Fernando Valley-chic vibe. In the Stories, as Karanikolaou walks into the well-appointed mansion, she says, “Praise be, bitches,” while Jenner is heard shouting, “Welcome to Gilead!”