Toyotomi Hideyoshi
Toyotomi Hideyoshi was a poor peasant's son who fought as a nose-in-the-trenches grunt in a strict, regimented, class-driven militaristic society that valued family honor and noble lineage above all things. Despite his inauspicious roots and lack of a recognizeable last name, this guy not only excelled at the art of war, but rose to the point where he became the de facto ruler of one of the most powerful industrialized military empires on the planet, the supreme commander of the Japanese army, and one of the most face-melting samurai warriors of all time.
That's so completely over-the-top insane that I can't even think of an analogy absurd enough to compare it to.
Hideyoshi was born in 1537 to some average Joe nobody who either worked as a woodcutter, an infantryman, a farmer, or some wacky metaphysical combination of those three professions. It's not really important in the grand scheme of things, because poor pops was toast by the time Hideyoshi was just thirteen, leaving this young peasant boy out on his ass to figure out what the hell he was going to do with his life. Hideyoshi tried his hand at entering a Buddhist temple, but xtreme head-shaving monkery really wasn't this guy's bag, and he quickly decided it would be far more lucrative to give up the simple life of monasticismness and go off to join a merry band of cutthroat murderous bandit thieves. Hideyoshi tooled around the countryside harassing innocent bystanders, robbing folks, punching old ladies, and generally being a bastard-faced blight on society, but eventually even that got boring as well. Fed up with kicking over strollers and shaking down laundromats, young Toyotomi tried his hand at being a blacksmith, a leatherworker, a wood carver, a fast-food fry technician, and pretty much every other job available to someone of his lineage. Nothing was really working out for him.
I was going to find some funny Demotivator about how much work sucks, but after I saw this I just stopped looking.
During his adventures wandering the Japanese country in search of a paycheck and a job that didn't completely lick Minotaur balls on fire, Hideyoshi somehow found employment as something called a "sandal-bearer" in the service of a soon-to-be-notorious feudal lord named Oda Nobunaga. Now I'm not entirely certain what exactly a "sandal-bearer" was actually responsible for in his day-to-day work (it seems pretty self-explanatory, but then again so does "Electronic Warfare Specialist" - and apparently that job has absolutely NOTHING to do with being really good at Call of Duty or Command & Conquer) but it's probably safe to say that this guy wasn't necessarily responsible for charging head-first into battle and single-handedly capturing enemy castles with nothing more than a Wakizashi and a really hard boner. I don't know, it just seems like there's no real way you can interpret the words "bearing" or "sandals" to make that job sound cool or interesting or not-utterly-soulcrushing. Still, Hideyoshi was sick of the nine-to-five bullshit he'd beeing going through, and he dedicated himself to serving bravely and honorably in any capacity that he could. It paid off big time.
Oda Nobunaga was a hardcore guy who knew a good badass when he saw one. Oda was quite the blood-spewing juggernaut himself (you can rest assured that I will be giving him his due diligence on this website at some point down the line) and it he took note of Hideyoshi's surprising balls-out attitude almost immediately. Initially, T-Hizzle he was lined up with those faceless soon-to-be-dead mooks that stand around like dumbasses in KOEI games trying to look vaguely menacing but honstely not really actually doing anything substantial, but it's obvious he didn't belong there. Hideyoshi's innate ability to forcibly kick ballsack sent him on the fast-track up the command structure, and time after time he prevailaed against superior forces using only his military tactical genius and his ability to kill lots of people when they least espect it. Like, one time this guy led a small group of badass Special Forces samurai asskickers up the side of Mount Inaba in the middle of the night to attack a heavily-defended castle from an unprotected side, and another time he crushed a besieged enemy army by having his soldiers re-route a river so that it flooded their fortress and drowned everybody inside. Shit like that gets you noticed, especially when you're working for a guy who's hatefully referred to across Japan as "The Demon King".
Toyotomi enjoying a moment of barefoot rock-climbing before slicing someone's face in half longways.
Toyotomi Hideyoshi would go on to serve Nobunaga for 24 years, rising through the ranks from sandal-bearing boot-licker to a Corps Commander who took those sandals, put Grizzly Bears in them, and then rammed them up his enemies' assholes. He and Nobunaga partied hard, smashed the balls off of a bunch of puny little city-state militias, and slowly but brutally unified the fragmented prefectures of Japan into one cohesive militaristic ass-kicking empire. Things went somewhat downhill in 1582 when Nobunaga was betrayed, sneak-attacked, and sworded to death by one of his own trusted generals, which bit. Apparently some dickmonger named Akechi Mitsuhideo was all pissed off or something just because the Demon King had ordered the dude's parents executed for treason or douchery or something along those lines, but I don't really get it, honestly.
Whatever the stupid reason behind this betrayal, however justified or otherwise, Hideyoshi wasn't about to let that shit go down on his watch. As soon as this righteous typhoon of pointiness heard word that Nobunaga had been assassinated, he launched a full-on attack at the castle he was besieging, captured it in two days, pulled a 180-degree handbrake turn, and hauled ass after Akechi Mitsuhide and bloody, bloody vengeance. Despite the pit stop to crush his enemies, Hideyoshi STILL managed to catch Akechi before he'd even been able to make his escape. Within seven days of Nobunaga's assassination, Akechi was dead at Hideyoshi's feet. Toyotomi personally presented the decapitated head of the traitorous general as part of his master's funeral procession. That is fucking awesome.
After a brief power struggle, Toyotomi Hideyoshi took over as the full-on commander of Nobunaga's army. By this point the Demon King had already captured a third of Japan, and had the military forces in place to complete the conquest, and Hideyoshi spent the next eight years slicing more faces than a Los Angeles county certified plastic surgeon. By 1590 he had conquered the entire country, and forcibly pacified all opposition. And of course when historians say "pacified", they mean "he impaled them with a katana or two until they were no longer breathing."
Hideyoshi ruled as supreme totalitarian dictator of Japan from 1590 until his death in 1598. Though his official title was something sort-of lame, like "Grand Master of State", he was basically the guy in charge. As they say, he had all the arquebuses, so he made the rules, and the figurehead Emperor and Shogun basically had no choice but to agree with whatever crazy bullshit Hideyoshi wanted to attempt. It was at this time that Hideyoshi changed his first name to Toyotomi, which means "Bountiful Minister", because I guess when you're the presidente-por-vida you can do whatever the hell you want with your names and nobody's going to give you a hard time. It was definitely an improvement over his old name, Kinoshita, which means "Under the Tree" and is also an anagram for "Shit in Oak", so that's something. In somewhat more historically-significant news, Hideyoshi also re-defined the military and feudal hierarchy , established new systems of land surveying and taxation, set up a full-time army, and then cemented his position against any possible revolutions by confiscating every sword in the country that didn't belong to one of his professional soldiers.
Hideyoshi's rise from faceless grunt to the Will of the Emperor was pretty damn impressive, but like all good super-powerful megalomaniacs, later on in his career as a tyrant this guy kind of flipped his shit and became moderately-to-severely psycho. First he crucified a bunch of perfectly-good Jesuits for no reason at all, then he had his nephew's entire extended family – like 30 people – publicly executed and tossed into a pit labeled "The Tomb of Traitors", even though it wasn't really a tomb and there wasn't a lot of evidence to suggest that they were traitors. After that he unsuccessfully tried to invade Korea. Twice. His self-professed plan the second time was to stack up a giant pile of severed ears in the middle of downtown Kyoto, which is suppose is kind of amusing in a Universal Soldier-sort of way (I guess you'd probably think it was less cool if you were Korean), but our old friend Yi Soon Shin smashed the entire Japanese navy into flotsam with his nutbag and that was about the end of that.
Despite the crippling boringness of his tax reforms and the failure to fulfill his dream of crushing Korea, conquering the Chinese Empire, and then eventually colonizing Alpha Centauri with samurai space cruisers and giant mecha robots, Toyotomi Hideyoshi is a pretty insane dude. This guy came from nothing, destroyed his enemies, conquered all of Japan, avenged his master's death, and then laid out the groundwork for a Shogunate that would control Japan for over three hundred years. Nowadays the Japanese regard him as one of their greatest historical heroes, and it's really tough to argue with them.
BADASS FASHION SENSE FTW