The 20 Best Trollings in Modern HistoryS

From the Spanish-American War all the way up to the 40 Hottest Women in Tech, the past century has borne witness to some epic trolling, bro. This amoral art form—loosely defined as "the media fucking with you on purpose"—has defined our modern era of outrage. It is time that we honored the very best trollings of the past 115 years.

The 20 Best Trollings in Modern HistoryS

The Spanish-American War
In 1898, our nation's glorious barons of yellow journalism decided that a war with Spain would be good for business. The sinking of the USS Maine in Cuba was attributed (in blaring headlines) to "Spanish Treachery" or "Enemy's Secret Infernal Machine," despite the fact that the Navy itself didn't know what had caused it. Oh well! Then we had a war. LOL.

The 20 Best Trollings in Modern HistoryS

"The War of the Worlds," by Orson Welles
In 1938, long before the Onion and the Daily Show, the American public's ability to detect fake news was at an all-time low. Still, the fact that thousands of people across the nation fell for a fake alien invasion (of New Jersey, of all places) goes to show that, had the internet been invented back then, the commenters would have been just as stupid as they are today.

The 20 Best Trollings in Modern HistoryS

Hitler, Man of the Year
"Look, our 'Man of the Year' is simply the most important person in the news that year. It is not a comment on their moral worth," Time Magazine people would say then, and forever after. Later at the bar, they cackled. "Hitler. I can't believe we actually did that shit."

The 20 Best Trollings in Modern HistoryS

"Is God Dead?"
The key is they ran this in 1966, when such a thing was considered provocative. (Also note the pioneering use of the Question Headline Used To Retain Plausible Deniability.) To achieve similar shockwaves today, the cover would have to be something far more thunderous, like "Is Justin Bieber Dead?"

The 20 Best Trollings in Modern HistoryS

"Oh, Wow"
In 1979, Joan Didion slammed Woody Allen (fairly!) in the pages of the New York Review of Books. John Romano, a Columbia professor, sent a letter of more than 600 words disputing Didion's complaints about Allen. To which Didion replied, in print: "Oh, wow."
This reply to an angry letter will never be topped.

Andy Kaufman's Feuds
Though not a member of the media per se, comedian-ish performance artist Andy Kaufman was more committed to fucking with the media than any other entertainer of his era. Perhaps the most impressive: his feud with pro wrestler Jerry "The King" Lawler, which caused Kaufman to break his neck (or did it???), was not revealed to be a hoax until ten years after Kaufman's death. That is the type of commitment to a "bit" that Gawker readers will appreciate in 2023, when it is revealed that "Caity Weaver" is simply a pen name adopted by the struggling former star Billy Crystal.

The 20 Best Trollings in Modern HistoryS

CYBERPORN
IT'S 1995 AND CYBERPORN IS COMING FOR YOUR KIDS—WHO ARE PROBABLY MASTURBATING RIGHT NOW (into your good sheets).

The 20 Best Trollings in Modern HistoryS

Roseanne Guest Edits the New Yorker
One could legitimately consider the entire Tina Brown era at the New Yorker as a large-scale and subtle act of trolling. But nothing drove it all home quite so well as when she had noted journalist Roseanne Barr guest edit the magazine in 1996, prompting some staffers to quit. Imagine if they'd known what Tina Brown would do at future magazines. At least Roseanne was alive!

The 20 Best Trollings in Modern HistoryS

Christopher Hitchens' Book-Length Takedown of Mother Teresa
Sure, he made a very viable argument. He also named his takedown of the world's most beloved nun "Missionary Position." It was even more incendiary than his later book-length takedown of god himself. Chris Hitchens was a master troll because he could devise a trollish idea ("Fuck Mother Teresa") and then actually pull it off. May he rest in peace, in hell.

The 20 Best Trollings in Modern HistoryS

Ayelet Waldman Loves Her Sexy Husband More Than Her Boring Baby
Ayelet Waldman, the writer wife of Michael Chabon, had to write a "Modern Love" column to let all of the mommies out there who are not having sex know: Ayelet Waldman is still having lots of sex, because she loves her husband more than her baby. That's right. Yeah, she said it. All she wants to do is to fuck her famous husband, who gave her HPV.

The 20 Best Trollings in Modern History

Zombie Princess Diana
Tina Brown's tenure as editor of Newsweek was the most complete and breathtaking example of sustained trolling ever undertaken at a major magazine. She put zombie Princess Diana on the cover and didn't even laugh about it. I mean... respect that troll. However...

The 20 Best Trollings in Modern History

"Muslim Rage"
By late 2012, Tina Brown was so bereft of real ideas that she'd resorted to simple xenophobia. This is trolling at its ugliest: a borderline racist caricature that appeals to its audience's basest emotions. Tina Brown is not a hero.

The 20 Best Trollings in Modern HistoryS

The Tiger Mom
Trolling is not about whether or not you have an actual argument; it's about how you make that argument. Amy Chua did, in fact, have an argument, about the merits of a particular parenting style. Then she wrapped it up in a brand called "Tiger Mom" and let the Wall Street Journal run an excerpt with the headline, "Why Chinese Mothers Are Superior." (She also advocated being a monster to your kids, for good measure.) Talking shit about someone's parenting skills is a great way to get them to spread your story around like the ebola virus.

The 20 Best Trollings in Modern History

Michael Wolff's Career
Michael Wolff is intelligent enough to be an actual, serious media critic; he's also canny enough to know that few people give a shit about serious media criticism, so he can get a lot more readers by tossing off ridiculous white whines about restaurant reservations and incendiary mansplanations; and, he's both needy and amoral enough to just, you know, insult people for attention. Michael Wolff, Le Trolle Extraordinaire.

The 20 Best Trollings in Modern HistoryS

The Atlantic's Vague Woman-Concern
As one of America's oldest and most respected magazines, the Atlantic has covered wars, politics, and everything else for many generations. But recently they discovered that nothing gets as many hits as vague meditations on unanswerable existential questions about women, such as whether they can "have it all." And hey, more power to them, clickety click click click. We, too, have always wondered, uh, whether women can, you know... get.... everything? *Checks traffic stats* Or not?

The 20 Best Trollings in Modern HistoryS

"Why Women Hate Me For Being Beautiful"
Samantha Brick wrote a feature for the Daily Mail about the trials and tribulations of being a beautiful woman. The story was illustrated with copious photos of Samantha Brick, who is not especially attractive. Five thousand seven hundred twenty five comments later, we know: It's a simple formula that really works.

The 20 Best Trollings in Modern HistoryS

Time Magazine on Attachment Parenting
Good cover.

The 20 Best Trollings in Modern HistoryS

"I Did Something So Horrible This Morning That I Can't Even Put It In My Headline"
XOJane.com is a site specializing in an advanced version of trolling in which A) a community of like-minded readers is cultivated and B) that community is led, little by little, to ever more ridiculous editorial horizons, until they wake up one day wondering, "What the fuck am I reading?" (That day has not come yet.) We could choose any number of gross articles about bodily functions to illustrate this point, but even better is this Emily McCombs post, "I Did Something So Horrible This Morning That I Can't Even Put It In My Headline," which, after blatantly refusing to state its own topic in the headline, still ends up being a gross article about bodily functions.
Do not try this at home.

The 20 Best Trollings in Modern HistoryS

The 40 Hottest Women in Tech There are plenty of "Hottest Women" slideshows, and there are plenty of poorly concealed sexist attention-grabbing honey traps, but none were done quite so ham-fistedly as Complex Magazine's thing last week. Right in the middle of a big argument about misogyny in the technology industry, Complex reminded everyone that women are for looking at. Guys, the formula is showing through the hot sexxxy see-through... computer screen. This attracted mega traffic precisely because it was so fucked up. Which is the point.

The 20 Best Trollings in Modern HistoryS

The Entire New York Times Style Section
On a weekly basis, nothing in American journalism comes close to the steady and dependably loathsome trolling of the New York Times Style section. We could list any one of hundreds upon hundreds of trolling examples from the section, which tend to be either "Straightfaced Story About Outrageous Rich People Behaving Outrageously, But We Act Like We Don't Realize That And We're Just Writing a Straight News Story, Which Will Only Make You More Mad," or "Completely Fabricated Trend." Your life will be much less rage-filled (we say from hard-earned experience) if you simply accept up front that the entire section is bullshit.

The 20 Best Trollings in Modern HistoryS

This Listicle
Thanks for clicking all the way through. Clickety click click click. LOL.

[Image by Jim Cooke. ]