History is packed full of unbelievable events, but some of the most unforgettable highlights were the underhanded tactics and savage insults people dished out to each other. Whether they were playful, hilarious, or just plain mean, the comebacks and cheap shots on this list left the public speechless. From politicians to celebrities, these perfectly timed burns came from all kinds of people. Some of these roasts changed opinions, some became popular quotes, and others simply lived on because they were just too legendary to forget. We’ve compiled 29 of the most savage roasts, comebacks, and cheap shots in history that are sure to leave you gasping.
#1
Winston Churchill, in his younger years, liked to drink. One time, when he was drunk at a party, a woman was very disapproving of his behavior. She said to him, “If I were your wife, I’d poison your coffee.” Churchill replied, “If I were your husband, I’d drink it.”
Image source: modern-prometheus, BiblioArchives / LibraryArchives
#2
When a couple of Frenchmen turned away from the Duke of Wellington at a diplomatic event, a woman apologized to him for their behavior. He responded by saying “I have seen their backs before, madam.”
Image source: -Crux-, Thomas Lawrence
#3
Phillip II if Macedon: “If I invade Laconia (Sparta) you will be destroyed, never to rise again.”
Sparta: “If”
Image source: Litotes, Oblomov2
#4
Benjamin Disraeli and a lord of sandwich, not sure which one:
“I do not know whether you shall die on the gallows or of the pox.”
“That depends whether I embrace your morals or your mistress”
Image source: alphanumericsprawl, Cornelius Jabez Hughes
#5
I don’t know if it can be considered a roast, but I always enjoyed the story of President Coolidge at a dinner party. Coolidge was known to be a man of few words and so the woman next to him informed him that she had bet someone she could get more than two words out of him, to which he replied “You lose.”
Image source: reddit.com, Harris & Ewing
#6
When France demanded that all US soldiers get off of French soil, and LBJ asked, “Does that include the ones buried at Normandy?”
Edit: President Lyndon B Johnson. Not Lebron James
Image source: champt0n, Arnold Newman
#7
After invading southern Greece and receiving the submission of other key city-states, Philip II of Macedon sent a message to Sparta: “If I invade Laconia you will be destroyed, never to rise again.”
The Spartan ephors replied with a single word: “If”.
Subsequently, neither Philip nor his son Alexander the Great attempted to capture the city. Philip is also recorded as approaching Sparta on another occasion and asking whether he should come as friend or foe; the reply was “Neither”.
Image source: LifeWin, Richard Mortel
#8
During the elections of 1800, Thomas Jefferson hired a newspaper editor named James Calendar to write and publish the mist vile things about his opponent, John Adams, including “Adams had a hideous, hermaphroditical character, which has neither the force and firmness of a man, nor the gentleness and sensibility of a woman.”
Image source: I-Do-Doodles, Rembrandt Peale
#9
This one comes from a really unlikely source.
A reporter once asked Mahatma Gandhi, “What do you think of western civilization?” He replies, “I think it would be a good idea.”
Image source: exhibit_Z, Elliott & Fry
#10
This letter sent by the Cleveland Browns to one of their season ticket holders.
Dude complained about paper airplanes and sent a letter into the Browns. They responded with “I feel you should be aware some asshole is signing your name to stupid letters.”
Image source: reddit.com, Erik Drost
#11
Stalin was angry at Tito, the ruler of Yugoslavia, because Tito refused to join the Warsaw pact. In retaliation, Stalin sent a number of Soviet assassins to try to kill Tito, all of which were unsuccessful.
In a letter to Stalin, Tito wrote this:
“Stop sending people to kill me. We’ve already captured five of them…If you don’t stop sending killers, I’ll send a very fast working one to Moscow. And I certainly won’t have to send another.”
Josip Broz Tito? More like Josip Brass Balls Tito.
Image source: sd51223, Digital Library of Slovenia
#12
In Plato’s Republic, Socrates, Thrasymachus, and a few other people are discussing what justice is. After everyone answers, Socrates argues against them and explains why their definition of justice is flawed. But he doesn’t put forth his own definition at first (he actually spends the majority of the rest of the book defining it through a system of government, but that’s not important).
Eventually Thrasymachus notices this and gets pissed. So (paraphrasing here) he says something like:
Socrates is playing his usual trick: not answering the question himself, but instead waiting for someone else to answer it, and then taking what he says and trying to prove it wrong.
It was pretty hilarious when I first read it.
Image source: chowder138, Greg O'Beirne
#13
“Shortly before World War I, the German Kaiser was the guest of the Swiss government to observe military maneuvers. The Kaiser asked a Swiss militiaman: ‘You are 500,000 and you shoot well, but if we attack with 1,000,000 men what will you do?’ The soldier replied: ‘We will shoot twice and go home.'”
Image source: echisholm, Marzio Bergomi
#14
Mozart didn’t like this singer so much that he wrote a piece for her with high and low notes constantly because he noticed that when she hit low notes her chin went to her chest and when she hit high notes her head would fling back. So it was like she was bobbing like a chicken
Image source: danielokane, Johann Nepomuk della Croce
#15
Stephen Hawking was in an interview, when a cord was unplugged, and alarm went off (this was before he was completely immobile), and he slumped in his chair. The people interviewing him were scared out of their minds, until they realized that he was alright, and chuckling at his joke. The cord and alarm were for a computer.
Image source: redsuslmao, ²°¹°°
#16
Steve Wilhite
He invented the gif, then he won a Webby Award for it. Webby Award speeches are only allowed to be five words long. He went up and said “it’s pronounced JIF, not GIF.”
Jod himself could come down and tell me that, I wouldn’t believe it. It’s GIF. Forever. Bye.
Image source: reddit.com, The Webby Awards
#17
The guy who opened a fake no 1 restaurant in London using Google reviews and his back garden and shed with microwave meals.
Image source: dirtyaccomplice, Jay Wennington
#18
In the 30s-40s BBC did an April fools broadcast where they told people how spaghetti was made… on trees. They literally showed fake spaghetti trees and since not many people in that time knew how spaghetti was made, lots of people believed it.
Image source: Voicedtunic, Robert Couse-Baker
#19
Technically this isn’t a troll since it was serving a purpose, but Admiral Nelson was escaping a French fleet when a man fell overboard. It was Nelson’s policy of never leaving anyone behind so he turned his ship around to go pick him up. The French saw his ship turn back toward them, assumed he had reinforcements coming beyond the horizon, so they turned and ran.
Image source: ScarletCaptain, Lemuel Francis Abbott
#20
Alexander the Great found the philosopher (Diogenes) looking attentively at a pile of human bones. Diogenes explained, “I am searching for the bones of your father but cannot distinguish them from those of a slave.
Image source: Xanderab, Wikimedia Commons
#21
Sultan Mehmed IV of the Ottoman Empire asked the Zaporozhian Cossacks (basically part of the Ukraine) to submit to him voluntarily after they beat his army in combat. Instead they wrote him a letter including such delightful turns of phrase as “What the devil kind of knight are you, that can’t slay a hedgehog with your naked arse?” and “the devil shits, and your army eats.”
Image source: panascope, Wikimedia Commons
#22
The old-timey NYC newspaper the Sun imo. In the 19th Century, they published some articles about the presence of life on the moon like unicorns, winged humans, and other creatures who built temples and lived peacefully. This caused a massive moon craze until it was later outed as fake.
Image source: reddit.com, Defunct publishers
#23
In China there was the war of the three kingdoms. The Wei, Shu, and Wu.
Two of their armies met in battle and the smaller was out of arrows. They were separated by a river. One night, the leader of the smaller army stocked the front of their boats/rafts with straw bales and moved toward the opposing army over the river. They were immediately hailed with arrows. The men ducked behind the straw while the arrows stuck in the straw, undamaged. They then sailed away and yelled.
“We thank you for the arrows, we will return them shortly!”
This may just be a tall tale from Romance of the Three Kingdoms but it may be true.
Image source: Mr_Caterpillar, Yu Ninjie
#24
Diogenese
He became notorious for his philosophical stunts, such as carrying a lamp during the day, claiming to be looking for an honest man. He criticized Plato, disputed his interpretation of Socrates, and sabotaged his lectures, sometimes distracting listeners by bringing food and eating during the discussions. Diogenes was also noted for having mocked Alexander the Great, both in public and to his face when he visited Corinth in 336 BC.
Image source: Anom8675309, Römisch-Germanisches Museum
#25
Gilles Corey. A farmer caught up in the Salem witch trials, he was sentenced to “pressing” (being slowly crushed by stones) to force him to make a plea.
Every time he was questioned, he simply said “More weight”.
He died without making a plea.
Image source: frachris87, factschology.com
#26
The guy that sent the first spam email.
On May 3, 1978, Gary Thuerk sent the first spam email on ARPANET, marketing the Decisystem-20 family of office computers. He succeeded in annoying many people, and the governing authorities even started a crackdown, stating: “Nobody should be allowed to send a message with a header that long, no matter what it is about.” Thuerk didn’t know it at the time, but he created a new type of email
Image source: FIBAgentNorton, Andrey Matveev
#27
Not super historical as the others, but my favorite. In the early 1960’s Ferrari dominated the 24 Hours of Le Mans, however they were not in a good financial situation so Henry Ford II Offered to buy the company and allow them to do their own thing.
Eventually a deal was worked out but at the contract signing something pissed off Enzo and he said he didn’t want the deal, Henry was pissed.
Henry then decided that Ford will be the dominate force in the 24. After a year or so of r&d Ford came out with the GT40. The next 3 years Ford took the top 3 spots and dethroned Ferrari.
Image source: jserpette95, Doug Coldwell
#28
TL;DR Husband gets killed, wife decides to literally burn an entire village to the ground.
Nah, you’re not explaining it brutally enough.
Her husband gets killed by members of a tribe, the Drevlians.
Since she’s now ruler (until her son is an adult, 10-15 years away), the Drevlian leaders ask her to marry their Prince.
She buries the 20 messengers alive.
She send a messenger to accept the proposal, and asks the Drevlians to send their best and brightest to accompany her on her travel to the Prince’s location.
They arrive, and she burns them to death in a bathhouse she had prepared for them after their long journey.
She invites a bunch of remaining dignitaries to a feast in her husband’s mourning, gets them and their retinues drunk, and has her soldiers slaughter the lot.
She makes her way around the country and basically ruins all their settlements. The Drevlians, being utterly screwed at this point and after a long seige, offer to buy her off with honey and furs. She instead asks for pigeons and sparrows, not wanting to “leave the poor peasants with nothing”.
She instructs her soldiers to render the birds inflammable, tying pieces of sulfur or kindling to them, and then releases them near the Drevlian Capital City of Iskorosten at dusk. Being birds, they all return home to roost for the night. She then sets the city alight, and razes it with thousands of burning birds carrying her payload. Her soldiers capture those who try to flee, kill a bunch, turn some into slaves, and order the rest to pay tribute to their new Queen.
TL;DR – Don’t kill a King and then ask the Queen to marry your Prince.
Image source: rachface636, Geminiilover
#29
My guy Heinrich Schliemann, father of modern archaeology. This dude was a fraud, con artist, an absolutely liar and legend. He wanted to discover the original Troy, and as such when someone else gave him a lead him to the alleged site, he BLEW UP THE REAL Troy because it “wasn’t old enough”, threw all the pieces in the trash, labelled the wrong layer of the city as the real Troy and took all the credit.
Image source: SadPermitRevoked, HeidICON
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