#2. Guam Tries to Borrow Ammunition from the Enemy
In the first stages of the Spanish-American War, USS Charleston was ordered to capture the Spanish island of Guam. They were running on a schedule, too -- they had been given only two days to complete this mission.
When they finally reached Guam, time was running short. With every reason to expect heavy resistance, they fired 13 shots at the shore fort of Santa Luz and waited for a response.
"Sir, you are sending the ammo too quickly for us to catch! Perhaps it would be easier to just hand it to us?"
The Spanish response was not the expected barrage of cannon fire and creative swearing. Instead they sent a single small ship, carrying a Spanish officer who politely asked permission to come aboard.
Out of curiosity, they let him. The Spaniard politely welcomed USS Charleston to Guam. Then, he thanked them for their lovely 13-shot salute ... and apologized that they had not saluted back as they were completely out of gunpowder. He proceeded to earnestly ask if the Americans would lend him some so they could return the favor.
Which prompted this expression from every crew member on board, simultaneously.
After what had to have been one of the most hilariously awkward conversations in the history of warfare, a confused and presumably very annoyed Spanish officer informed the Americans that Spain had never bothered to inform Guam that they were at war with the U.S. at all, and that in fact several battles had already occurred. This would be why, for instance, they didn't bother stocking up on gunpowder.
This is how the strategically important island surrendered without firing a single shot, presumably because a "WE ARE AT WAR" email got stuck in Guam's spam folder.
#1. Stonewall Jackson Is Gunned Down by His Own Men
When General Lee split his troops during the battle, he gave Jackson the all-important task of attacking the Union flank. Stonewall obliged by raising his trademark hell, tearing through the opposition like the unstoppable force of nature that he was. He only stopped his attack because nightfall made it too dark for accurate dick punching.
"Don't fire until you see the bulge in their pants!"
Look, friendly fire is going to happen. Real war isn't like a video game -- there are no icons hovering over your teammates' heads. But there is friendly fire and then there is accidentally shooting one of the most legendary generals in the history of warfare.
It happened thanks to Jackson's typical bravado. He had a mind to take the fight to the enemy the second he could, and was keen on running reconnaissance on the Union's formations. So keen, in fact, that he just couldn't wait for any actual intelligence officers to gather the knowledge he desired, let alone wait for them to explain that shit to him. No, he was going to ride out and do the spying himself.
Presumably while yelling "I am a spy! I am spying directly upon you!"
So out beyond the Confederate lines he rode, accompanied by just a small entourage. When one of his officers pointed out that wandering out beyond your own lines in the aftermath of a battle at night might be a tad dangerous, Jackson assured the man that it was all good and ordered him to go and tell everyone to prepare for opening yet another tin of whoop-ass on the enemy, Stonewall style.
However, Jackson failed to realize two very important things.
Thing number one: Your average soldier isn't Stonewall Jackson, or even all that brave. He's cold, and tired, and hungry, and terrified out of his skull of the darkness beyond his picket. And most importantly, he's scared enough to fire at any suspicious movement -- especially if said movement rides directly toward him at high speed, booming that he's your own high commander.
It didn't help that he changed his name every time he thought of a cool new one. This time it was "Punchbeard Solowar."
Thing number two: Jackson was now coming in from the exact direction these men were pointing their guns.
Thus, Stonewall and his returning party were greeted with gunfire the very second Confederate sentries saw him. The general took three bullets, had an arm amputated and succumbed to operation-induced pneumonia eight days later. And that's how a few random sentries wound up with an incredibly awkward story to tell their families back home.
For more real-life scenarios that could've been set to Yakety Sax, check out 6 People Who Faked Their Own Death (For Ridiculous Reasons) and 5 Movie Martial Artists That Lost a Deathmatch to Dignity.