#2. Abraham Lincoln Led a Bumbling Backwoods Militia (and Wrestled Them)
Before he was given the task of crushing the Southern rebellion, Abraham Lincoln volunteered to help crush a Native American rebellion back when he was 23, during what was called the Black Hawk War. It took place in 1832 after a group of Native Americans crossed the Mississippi River into Illinois to reclaim their land from white settlers and had almost nothing to do with the professional hockey team of the same name.
It was named after the Kickapoo twin-engine chopper.
In response, the government scrambled to put a militia force together, and Honest Abe was voted company commander of his band of volunteer soldiers. Although Lincoln was proud of being entrusted with this command, it was reported by the men that the appeal of electing him as their officer was that they were able to do whatever they wanted. Serving under Abraham Lincoln was apparently less like Full Metal Jacket and more like Our Gang and/or The Goonies.
For example, like most modern-day rural militias, Lincoln's company never saw actual combat. But they did spend plenty of time drinking all of their whiskey supplies, which was something they used to issue to soldiers because conventional wisdom has worn many strange masks over the centuries. When Lincoln's troops ran out of their own booze, they teamed up with a neighboring company to use tomahawks and buckets to raid the officers' stockpile of wine and brandy.
When Abe awoke, he discovered that someone had shaved his mustache.
Lincoln tried to call his men into formation the next morning, but they were nestled peacefully beneath a hazy cloud of sleepy booze farts and didn't manage to crawl out of bed until after 10 o'clock, by which time the rest of the militia companies had already left them far behind. Lincoln's troops managed to march about 2 miles before simply giving up and going back to sleep to cast off the rest of their hangovers. Lincoln was arrested and forced carry a wooden sword for two days as punishment, because old-timey justice was occasionally hilarious.
Despite the fact that his men made almost no effort to listen to anything he said, Lincoln still had a blast being a militia captain because he got to engage in impromptu wrestling matches with the other soldiers. And if there was one thing Abraham Lincoln loved, it was kicking people's asses. He gained a reputation as the best wrestler in the army, because apparently they just wrestled all the time instead of actually trying to quell the Indian rebellion they had been mustered together to pacify. Abe lost only one of his completely insane wrestling matches, to a man named Thompson, a soldier from a different company whom he battled for the right to choose the best camping spot, according to an actual historical document containing the sentence, "At last the man got the crotch lock on Mr. Lincoln."
#1. College Student James Monroe Ransacked the Governor's House
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When 16-year-old James Monroe was attending the College of William and Mary in 1775, one of the most popular extracurricular activities for the young student body was to harass the local British governor in the name of the impending American Revolution. As opposed to the type of civil disobedience that currently takes place at William and Mary (which consists mostly of purchasing licensed merchandise from a movie by the Wachowskis and reblogging things), Monroe and his buddies would march around on the college green deliberately trying to provoke the stationed British soldiers.
They'd dance beside the signs reading "Keep off the grass."
And because there were no panty raids in 1775 (largely due to the fact that women were forbidden by law to come anywhere near an institution of higher learning), Monroe led his colonial Animal House on a raid of the next best thing -- an enormous stockpile of weapons from the governor's mansion.
See, the colonies were scant months away from full-blown war with England, and tensions were pretty high. So the Royal Governor of the Colony of Virginia, Lord Dunmore, thought the best way to keep the peace in the little slice of stolen Powhatan land the crown had tasked him to protect was to keep a goddamned arsenal on display in the Governor's Palace at all times. This seems to suggest that Lord Dunmore's appointment was largely political, and not at all related to any demonstrable ability to govern things.
He thought the guns were pretty.
Anyway, when the militia fighting started to get serious, Lord Dunmore packed his royal bags and got the hell out of town, abandoning his mansion with everything still left inside (although he presumably stopped at a few local taverns to spread the word that it was haunted in order to keep it safe from plundering colonists). Monroe saw his opportunity for the biggest college prank ever and raided the palace, loading up around 200 muskets, 300 swords, and 18 pistols that were delivered directly to the local militia.
Again, these were all weapons that Lord Dunmore just left behind in his house like stacks of old Pokemon cards (see "terrible governor," above). Monroe dropped out soon after to join the fighting and never did earn his degree, which didn't stop him from achieving the highest office in the land, in case you were wondering how little college matters (answer: not at all, if you are sufficiently ambitious and/or insane).
Related Reading: Did you know LBJ had a huge wang and slept with waaaay more women than JFK? It's true! Oh, and Andrew Jackson was a murderous lunatic. And guess what- Teddy Roosevelt kept a damn badger in the White House.