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What Makes a Tweet the ‘Worst of All Time’?

We asked the experts who have made a bracket to try and find out

I used to care about lots of tweets. I once tried to collect the hundred or so amazing tweets I regard as canonical — proof of the social network’s value. Of course, there are many more bad tweets than good; almost daily you encounter some tweet that makes a credible case for itself as the worst of all time. At this moment, these are the only tweets I’m interested in, because they make up the 2018 Worst Tweet of All Time Bracket, a side project from Sam Sacks and Sam Knight, co-creators of a watchdog news site and podcast called the District Sentinel. They’re mounting this March Madness-style tournament with the account @WorstDamnTweet, and I have to say: trying to gauge the relative badness of each entry is breaking my brain — that’s how stiff the competition is.

Although the matchups, including play-in rounds, are decided by the voting of the Twitter Mob, the selection and organization of these appalling tweets present a compelling idea of what makes for a truly stupid tweet. Immediately we notice the robust representation of political takes and personae; five of the eight regions have an explicit connection to the field, from D.C. pundits and cable news anchors to far-right trolls and our absolute dumbest elected officials. Even those in the Celebrity and “Extremely Online” categories are typically signaling or dissecting politics in their garbage tweets, as when #Resistance fighter Eric Garland first embarked on his Adderall-fueled “game theory” thread. There can be no doubt about it: wading into the Beltway muck raises your chances of authoring a memorably shitty tweet by at least a thousand percent.

“We honestly tried not to make it too political,” Knight and Sacks told me via Twitter DM, “but we also wanted to make sure that most of the entrants were actually relevant people and not just randoms, hence a lot of politico-types are represented.”

This brings us to another qualification. For a bad tweet to achieve legendary status, it needs exposure. Scientifically speaking, the worst tweet of all time is almost certain to come from a verified account with thousands if not millions of fans — an audience that presumably takes the person’s opinions seriously. (A notable exception is Justine Sacco’s racist tweet about AIDS in Africa, which went unaccountably viral and ruined her life despite the fact that she had fewer than 200 followers at the time.) A dumb tweet from, say, J.K. Rowling, is far more aggravating than the same dumb tweet from some anonymous schmuck because you know there are tons of idiots out there liking and retweeting it. You can actually see those numbers. Internet celebrity, then, is a crucial factor in determining worst tweets. The same people, as the Sams explained to me, “come from notable bubbles: The Acela Corridor (NY-DC), Hollywood, Capitol Hill, etc.”

“Places where people don’t often think before they tweet: ‘Hey, am I and my friends the only ones who subscribe to this wacky-ass idea?’’’ the Sams clarified. “So it leads to people posting truly insane shit without even realizing it. For example, Ezra Klein is completely clueless that people experience political violence in the U.S. all the time because he personally never experiences it. Or the belief that a team of troops could beat an NFL team. You can only arrive at that conclusion after living in a conservative bubble or being regularly fed Jake Tapper tweets.” A profound lack of self-awareness (or grounding in the national reality) is an indispensable advantage for a bad tweet.

It must be said, too, that many @WorstDamnTweet contestants are notorious for tweeting badly as a matter of course. Concocting candidates for the worst tweet of all time is, as they say, very “on brand” for these users. Whereas a guy like Kanye West is just a loose cannon who produced many fine, funny tweets before randomly and tragically declaring “BILL COSBY INNOCENT !!!!!!!!!!” in 2016, CNN’s terminally myopic Chris Cillizza has all but made a sport of getting demolished by The Ratio, a phenomenon that occurs when a horrendous tweet receives few endorsements and scores of angry, mocking replies. It is left to the observer, therefore, to figure out which dumbass tweet in Cillizza’s pantheon of stunningly dumbass tweets is the dumbassest of the bunch. The Sams have made the canny choice — one I agree with — to enshrine tweets from serial offenders like Cillizza which already serve as historic landmarks.

“We wanted to pick tweets that were both really bad and recognizable,” they told me. “As soon as people saw them, they’d be like, ‘Oh yeah, I remember that garbage!’” At the same time, they “wanted to be careful about not promoting stuff that was too offensively racist, Islamophobic, homophobic, or whatever. These awful tweets (many of which have been deleted along with their accounts), are going to be making the rounds again, so we didn’t want things too offensive out there.” Therefore, while Infowars goblin Paul Joseph Watson spouts vile hatred on Twitter virtually 24/7, it made sense to instead commemorate the pathetic beauty of his saddest cultural analogy:

So there you have the most reliable parameters for atrocious tweets: 1) political and 2) tweeted by a prominent figure who 3) has no clue how their comment reads to anyone without brain-worms. Once in a while, a pure and revolting non-sequitur can ascend to mythic levels of disgrace — see director Kevin Smith’s graphic tweet regarding married sex — but the roots of bone-crushingly bad tweets are usually ideological. My own takeaway from this is that we are fairly tolerant, up to a point, of offensive and ignorant content that lacks a significant platform or doesn’t directly pertain to the monstrosities of war, torture, disease, poverty, and other blights that exact a heavy human cost.

Is there any chance of eliminating this crap? Don’t get your hopes up — it’s a natural element of the digital ecosystem. “We do hope some of these accounts take notice,” the Sams said. “So far none have blocked us. But this tournament won’t end bad tweets. In fact, this tournament needs them to exist. The best thing we can hope for now is bring accountability to the shit take lords.” Regardless, a new generation will emerge. The bigger you get on Twitter, and the deeper you sink into its logic, the more off-putting and isolated you are, and the more inevitable your worst tweet ever becomes. Meaning that the only surefire way to stay out of a bracket like this is, as always, to never tweet.

But do make sure to vote in @WorstDamnTweet — now that you’re an expert, I mean.