Let’s face it: while important figures in history may have had some serious titles to uphold, they certainly weren’t immune to the hilarity of being human. They were just as prone to making mistakes, pulling pranks and stirring up trouble as the descendants (us…) that they left behind.
Emperors, princes, presidents, war leaders, philosophers, and many other of histories greatest people have left some pretty funny stories behind from their time in power. You might not think that war and politics would be natural sources for comedy gold, but as our ancestors show, sometimes the horrors of battle or the mundanity of politics produce some real knee-slappers.
45. I’m Sailing Away
44. Funky Shootout
43. Grace Under Fire
I’ve always found the antics of the USS William D Porter, a U.S. Navy Destroyer in WWII, to be comical. Amongst other things, the Porter accidentally fired a live torpedo at the USS Iowa while President Roosevelt was on board for a top secret trip to North Africa.
The story comes off as a slapstick comedy come to life.
42. Toilet Humor
41. Never Friendzone Charlie
In the 1600s, Prince Charles of England and the Spanish princess Maria Anna were supposed to be wed, as a huge diplomatic deal between the two countries.
Due to political issues the negotiations took nine years, Spain was essentially stalling for time to keep Britain peaceful, pretending that there were religious troubles. Eventually Prince Charles and the Duke of Buckingham sailed for Spain (in secret, on their own initiative, much to the alarm of King James of England when they vanished and the British ambassador in Spain when they showed up) in an attempt to woo the princess, thinking that it would really work.
The princess had zero intention of ever marrying Charles and so they went home in disgrace.
Two years later Charles, now King, attacked Spain. The previous King and parliament had massive fallouts over this sensitive political issue, Charles assumed that by just launching an attack everything would sort itself out.
The commander, Cecil, planned to raid Spanish treasure ships but missed them due to a storm. He went ahead with the invasion woefully unprepared. He attacked a port city and found many Spanish ships there, but didn’t give the order to attack (thinking his fleet would take the initiative) so they escaped.
He executed a very difficult and costly attack on a fort, which succeeded, then realised that was of no use whatsoever in capturing the actual city, which was one of the most heavily defended in Spain.
The English hadn’t brought enough food with them so Cecil was forced to allow his men to ransack the local pubs, and they all got quite inebriated.
The Spanish showed up and Cecil had to retreat, the 1,000 men who got left behind were too inebriated to defend themselves and were executed. The fleet retreated to England and missed yet another raiding opportunity.
They got no loot and caused no damage to the Spanish.
Because King Charles’ best mate (and probable lover) the Duke of Buckingham had organised this farce, Charles refused to acknowledge the colossal failure and just let it go.
Parliament was outraged and impeached the Duke, but Charles dissolved the parliament, setting the tone for his entire reign. Some years later, after a lot more ridiculous conflict between the King and Parliament, civil war breaks out, the King is beheaded, and the monarchy suspended.
It never regains the power it used to have and parliament runs the country forever.
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40. Kicking The Bucket
I present you, the War of the Bucket.
In 1325 there was rivalry between the city-states of Bologna and Modena.
A few Modenense soldiers stole a bucket from a well in Bologna, and war was started (even though there had been conflicts for 300 years between them).
The war was won by Modena, so the bucket still remains in Modena.
39. Still Not The Most Absurd Crusade
38. Monkey Business
During the Napoleonic Wars, a French ship wrecked along a remote shore of England.
The lone survivor was the captain’s pet monkey, dressed in a little army uniform. The locals, having never seen a Frenchman before, assumed he was French.
They arrested, tried, and convicted him for being a French spy.
When they hanged him, the monkey kept climbing up the rope, proving to be an elusive victim of capitol punishment.
To this day, the residents of Hartlepool are known as Monkey Hangers.
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37. Attack Of The Neutrals
Switzerland — the world’s most famous neutral country — “invaded” Liechtenstein in 2007 with 170 soldiers.
What happened was that the infantry accidentally crossed over the border, discovered their mistake, turned back, and made the call up the chain to to explain themselves so the Swiss government could apologize.
Liechtenstein didn’t know it had happened until they got the apology.
36. Dic-taters
This is the best case of reverse psychology in history.
35. President For Life
34. Simon Fez
In 1925 the first President of Turkey banned fez hats. This caused a sudden uptick in fez smuggling and riots supporting the hat.
33. Hassle In The Castle
The battle for Castle Itter in World War II was one of the weirdest ever. Simply reading the list of those involved sounds like a joke!
On one side, you have :
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14 American Soldiers with a tank
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10 German Army soldiers (yes, German soldiers)
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One German from the Waffen SS
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French VIP prisoners (among them: a former prime minister and a famous tennis player)
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One Austrian
On the other, you have about 100 German SS soldiers.
End result:
the SS were almost all captured, and the German army officer sacrificed himself to protect the French ex-prime minister from a sniper.
32. This Dexter Isn’t A Genius
My favorite historical absurdity is the life of American merchant Timothy Dexter, the luckiest idiot to ever live. Among his exploits:
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Sent warming pans to the (very, very warm) West Indies. His captain sold them as molasses ladles. Made a profit.
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Sent wool mittens to the same place, sold them to a passing Asian trader for export to Siberia.
AdvertisementMade a profit.
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Literally shipped coal to Newcastle (a huge exporter of coal). Showed up during a miner’s strike and sold it at a huge markup to the other traders waiting for it to end.
AdvertisementMade a profit.
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Shipped bibles to the East Indies. Sold them to missionaries. Made a profit.
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Shipped cats to the Caribbean. Turns out there was a massive rat infestation at the time.
AdvertisementMade a profit.
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Hoarded whalebone by accident. Sold it for use in corsets. Made a profit.
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Faked his own death, attended his own funeral, and caned his wife for not crying enough.
AdvertisementPresumably didn’t make a profit.
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Bought an opulent mansion, with statues of George Washington, Napoleon Bonaparte, Thomas Jefferson, William Pitt, and himself, with the inscription “I am the first in the East, the first in the West, and the greatest philosopher in the Western World”.
AdvertisementLived in it for the rest of his days, which is sort of like making a profit.
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Wrote a rambling, incoherent book with inconsistent capitalization and no punctuation; printed a second edition with a few extra pages filled with nothing but punctuation, instructing readers to “peper and solt it as they plese”.
AdvertisementMade a profit.
31. Lay Off The Wine?
30. Vidi Vici Veni
29. A Very Loud Hello
The capture of Guam during the Spanish-American war was pretty absurd.
An American ship appeared and started shooting warning shots towards a fort on Guam.
In response, a rowboat is sent out from the fort with two people. Upon reaching the American ship they say that they are delighted to have some visitors and that they would return the salute if they only had some gunpowder.
They were surprised to learn that the US and Spain were at war and that they were now prisoners.
28. This One’s A Bit Emutional
The time Australia lost a war to some emus… that’s pretty funny.
Emus were threatening Australian farmland, so the government sent in the army to machine gun the emus. The troops were recalled after a series of embarrassing failures, which resulted in “only a few” emus being killed.
27. Burn, Baby, Burn
26. Surgical Strike
25. Accidental British Cobra Epidemic
The British government wanted to get rid of the cobras in India, so they started offering money for cobra corpses. To take advantage of this, many people started breeding cobras to kill for the money, so they stopped buying cobra corpses once they realized it was going on.
All of the cobra breeders released the snakes and there ended up being even more cobras than there had been in the first place.
24. Duplicating A “Better” City
During the Byzantine-Sassanian wars in the early 6th century, Khosrau I of Persia destroyed Antioch and captured its civilians.
However, rather than enslaving them or ending their lives, Khosrau brought them back to Persia and rebuilt them an almost exact replica of Antioch, down to the layout of the city and rooms in the houses.
The citizens were freed and made into full Persian citizens.
The city was named “Weh Antiok Khosrau” – “Khosrau’s better Antioch”
23. An Inappropriate Grand Prix Birthday Celebration
One of my favorite funny stories is that in 1977.
Australian Formula 1 driver Alan Jones won the Austrian Grand Prix. No one expected him to win, so the organizers didn’t have the Australian national anthem on hand to play at the ceremony after the race.
Instead, some under the influence random person started playing “Happy Birthday” on the trumpet.
The race happened in August. Jones’ birthday is in November.
22. Careless City-Conquerer Admitting His Guilt
When Britain was fighting to conquer India, a General named Charles James Napier was told not to attack the city of Sindh.
However, he had an opportunity, went ahead and attacked Sindh, and captured it.
When he sent news back to Britain of his victory, his telegram was a single word:
“Peccavi”.
This is not an English word, but a Latin one and most people know of it through the Catholic church. Directly translated into English it means, “I have sinned”.
21. An Experiment Over A Coffee Phobia
King Gustav III of Sweden was convinced that coffee was poisonous and dangerous to public health.
He levied heavy taxes on coffee and even passed a royal edict banning it, however, its consumption became ever more popular.
Determined to prove its danger, he ordered an experiment carried out:
two identical twins had their death sentences commuted to life imprisonment, on the condition one drank three pots of coffee a day, and the other three pots of tea.
Physicians would monitor the effects and report their eventual demise to the King.
Both of these physicians died of natural causes before this happened, however.
Even King Gustav was assassinated in 1792 before either of the twins had met their end. Eventually, the tea drinker was the first to pass away, at 83 years of age.
His brother’s age is not known.
20. Austria’s Accidental Attack Against Itself
In 1788 two portions of an Austrian army attacked each other by accident near the city of Karánsebes. Two days later the Ottoman enemy showed up and took the city without a fight as all that was left were corpses and wounded Austrians.
19. Prank-Landing Of A Stolen Plane
One of my favorites is in 1956, for a bet and while under the influence, a man named Tommy Fitzpatrick stole a small plane from New Jersey and then landed it perfectly on the narrow street in front of the bar he had been drinking at in New York City.
Then, two years later, he did it again after someone didn’t believe he had done it the first time.
18. Australia’s Accident-Avoidant Gold Medal Speedskater
Australia’s first gold medal at the Winter Olympics was in speedskating.
The skater (Steven Bradbury) was coming last until every single athlete in front of him fell over.
The best part is that he was only in the finals because the exact same thing happened in the semifinals. To this day, an incredibly unlikely victory is known as ‘pulling a Bradbury’ in Australia.
17. A Royal Weapon Of A Chinese Board Game
In ancient China, there was a board game called liubo. The rules haven’t survived to the modern day, but archaeologists have found the stone boards and playing pieces in tombs, and it’s mentioned quite a bit in historical texts.
Most notably, not one, but two separate imperial princes from different dynasties are recorded as having killed a relative by smashing them over the head with a liubo board.
16. A Drunk King’s Fall From His Castle
Charles XII of Sweden was a proper party king in his youth, at one of his many parties he got a bear so under the influence it fell out of a castle window and died.
15. Lincoln’s Hysterically Dry Humor
Abraham Lincoln had a dry sense of humor.
He once answered a question about whether his legs were too long by saying, “I have not given the matter much consideration, but on first blush, I should judge they ought to be long enough to reach from his body to the ground”.
Regarding General McClellan–who was skilled at training soldiers but reluctant to send them into combat–Lincoln quipped, “If General McClellan doesn’t want to use his army, I’d like to borrow it”.
Then–this last one is disputed yet was reported in reputable newspapers in 1863–when a congressional delegation complained that General Grant had too many drinks, Lincoln reportedly replied that he would like to know what Grant drinks so he could send a case to each of his other generals.
14. Philosopher Diogenes’ Extreme Confidence
It was in Corinth that a meeting between Alexander the Great and Diogenes is supposed to have taken place.
These stories may be apocryphal. The accounts of Plutarch and Diogenes Laërtius recount that they exchanged only a few words: while Diogenes was relaxing in the morning sunlight, Alexander, thrilled to meet the famous philosopher, asked if there was any favor he might do for him.
Diogenes replied, “Yes, stand out of my sunlight”. Alexander then declared, “If I were not Alexander, then I should wish to be Diogenes”. “If I were not Diogenes, I would still wish to be Diogenes,” Diogenes replied.
13. Pirate-Kidnapped Julius Ceasar’s Sarcasm
Once Julius Caesar was kidnapped by pirates, who demanded a ransom of 20 talents. He laughed and told them that they did not know who they had captured, and suggested 50 talents as a much more suitable sum.
While he was a hostage, he acted like their commander rather than their prisoner. He would tell them to stop talking when he wanted to sleep and read them his own poetry (calling them illiterate idiots when they weren’t impressed enough).
Once he was freed, he had all the pirates captured and crucified.
12. The High-Maintenance, Financially Reckless Founding Fathers
I’m a historian whose specialty is the American Revolutionary Era. I think one of the more humorous things about this period is that almost every single Founding Father were worse at managing personal finances than the average American is today (yes, it was that bad).
Seriously, by 1790, they had all amassed a crazy amount of debt, a lot of it was on extreme extravagances, like Washington ordering marble from Italy for his new fireplace or ordering green wallpaper (the most expensive color in the 18th century) from Northern Europe.
Many of them were simply drowning in debt and had no clear plans for getting themselves out of it.
11. A French Monkey On Trial
There’s a community in the UK, in and around Hartlepool who are known as “Monkey Hangers”
“According to local folklore, the term originates from an incident in which a monkey was hanged in Hartlepool, England. During the Napoleonic Wars, a French ship of the type chasse marée was wrecked off the coast of Hartlepool. The only survivor was a monkey, allegedly wearing a French uniform to provide amusement for the crew.
On finding the monkey, some locals decided to hold an impromptu trial on the beach; since the monkey was unable to answer their questions and because they had seen neither a monkey nor a Frenchman before, they concluded that the monkey was, in fact, a French spy.
Being found guilty the animal was duly sentenced to death and hanged on the beach”.
10. Stalin’s Many Failed Assassination Attempts
Stalin kept trying to assassinate Josip Broz Tito. Tito sent this letter to Stalin:
“Stop sending people to kill me! We’ve already captured five of them, one of them with an explosive and another with a weapon… 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”.
9. A Flying Turtle And A Priest Horse
My brother studies ancient history, so I’ve heard a few good ones. In 455 BC, the ancient Greek playwriter Aeschylus spent all his time outside after hearing a prophecy that he would be killed by a falling object.
He later got killed by a turtle that an eagle had dropped on his head after mistaking it for a rock.
Another funny one is the Roman emperor Caligula had such a strong connection with his horse that he appointed him as a priest, and was planning to make him a senator before he got assassinated.
8. An Under The Influence Crusade To Capture Fort Ticonderoga
My usual standby to this is that the infamous attack on Fort Ticonderoga by the Green Mountain Boys during American Revolution, which provided Washington with a lot of sorely needed cannons… was literally a case of “hold my drink”.
The leader of the Green Mountain Boys and his group liked to drink… a lot… in this bar that could see the fort. One day during the Revolutionary War, they got REALLY under the influence and had a conversation that effectively went “Hey… hey guys… guys… I think… we could… I think we could just… TAKE… that fort”!
“You are absolutely smashed! There’s… there’s no way! I mean… wait… no… that might work… huh”.
So they went out and took the fort, just to see if they could.
Afterward, they had a lot of cannons and few drinks. So they sold Washington the cannons (despite largely having a desire for him to lose to the British) so they could reverse this equation.
7. Sword-Wielding, War-Hungry Churchill
Jack Churchill was the last man to use a sword in battle, and he stormed Normandy with a Claymore. He single-handedly took out 42 Germans who were armed to the gills with only his broadsword and was upset when the Americans dropped the bomb and ended the war because he wanted to keep on fighting.
Definitely a colorful character worth looking into from WWII
6. French Capturing The Dutch On Thin Ice
The battle of Texel. In 1795, a Dutch fleet of 14 ships and 850 weapons got frozen on/in a lake. The French Calvary road on the ice, and ended up capturing the ships, weapons, and some other merchant ships.
Think about that — French dudes on horseback won a naval battle.
5. Rome’s Sacred, War-Signalling Chickens
The Sacred Chickens of Rome. See before a battle in the ancient era you used various divination techniques to see how the battle was going to turn out or whom the gods favored etc.
Well, one of the techniques the Romans used were chickens. They would throw out some seed, and if the sacred chickens ate, then it meant it was time to fight.
If they wouldn’t eat, that meant it’s time to flee.
During the war with Carthage, a Roman admiral used the sacred chickens before a battle, and they wouldn’t eat.
So he said “maybe they are thirsty,” and kicked them overboard. He lost the battle spectacularly, and learned a valuable lesson — always listen to the sacred chickens.
4. An Attack On The Aztecs With A Wooden Slingshot
There’s an indigenous account from the siege of Tenochtitlan, the Aztec capital, in which the conquistadors were trying to get the Aztecs to surrender the city.
One day, the conquistadors got pretty close to the city walls and started building something out of wood.
The Aztecs were keeping an eye on them, but couldn’t understand their language. The Spanish started arguing amongst themselves a bit, and one guy, in particular, was throwing his weight around and pointing.
They all kept building but kept having arguments. Many hours later, construction was complete; turns out, they’d been building a trebuchet.
The Spanish finally start getting ready to fling some big rocks at the Aztecs.
The Aztecs watched as the Spanish managed to fling a boulder about 20 feet into the lake that surrounds the city. The Spanish argued more. They tried again and managed to smash a hole in a wall of the marketplace, but the thing takes so long to aim that by the time it hit, the Aztecs have cleared all their stuff out of the way. The Spanish argued more, then wheeled the trebuchet away in shame.
It was never seen again.
3. General Patton’s Hilarious Capture Of Trier
In WWII, General Eisenhower sent a message to General Patton, telling him to bypass Trier because it would take 4 divisions to capture.
Patton’s response: “Have taken Trier with two divisions. What do you want me to do? Give it back”?
2. Crushing The Pastry Of Royalty
When the Princess Royal Victoria (Queen Victoria’s eldest daughter) and her new husband Fritz (second in line to the Prussian throne) were on their way back to Prussia after being married in England, they stopped by the town of Wittenberg.
The townspeople baked Vicky (as she was known) and Fritz a big apple tart famous from their area. A while later a Prussian field-marshal named Wrangel boarded the train.
He did not look where he sat down and so he sat right on top of the pastry, collapsing into it. He took it in good humor and ordered a rush change of clothes.
1. Arabic Scholar Who Knew How To Party
Al-Khatib Al-Baghdadi was an eleventh-century Arabic scholar, philosopher, and theologian. He spent his early twenties traveling what is now Iraq and Persia, recording the different regional traditions.
He wrote several influential books about hadith, a key aspect of Islam, as well as the defining history of the city of Baghdad. He also wrote a guidebook on how to crash parties.
