5. Gill (Street Fighter III: Third Strike)
Being a ludicrous, popsicle-colored boss with a god complex is probably enough to earn ol' Gill a spot on this list. What's truly diabolical about him, though, is his out-of-this-world cheapness. We've got a boss here who's such a cheat that, if you beat him, his super bar will actually restart the match with him back at full health. That should never happen, man! This beautiful turd has obviously been getting special treatment his whole life, and that helping hand continues to prop him up in what's supposed to be a street fight. Everyone else stays down when they get K.O.'ed, but no, it's different for Gill. It alway has been for Gill.
The sense of entitlement even radiates from his backstory. This blond bombshell of a false messiah is the leader of an Illuminati-esque cult that comes with all the requisite shadowy, cloaked figures and sexy personal assistants. He claims to truly be interested in uniting the human race, but it's such posturing and hollow rhetoric that you can honestly just smell the scent of bullshit on that rocky mediterranean beach his stage is set at. C'mon... dude's so conceited that one of his signature specials involves him opening his heavenly wings and flexing his heavenly body. This is the kind of savior who would kick sand in your face on the beach and steal your girlfriend without apology. Seriously, screw this guy.
4. Geese Howard (Fatal Fury)
Were you, oh gentle browser, able to call this one? Don't worry - even Geese knows he's a predictabo choice. You don't need to pat your back on this guess, pal.
Many other evil businessmen cum evil martial arts champions have followed Mr. Howard, but credit must still be given to the scumbag who set the standard. He's basically a vision of what Fatal Fury's hometown hero, Terry Bogard, might turn into with that oh-so-corrupting money 'n power stuff. What truly sets Geese apart, though, is that he's a boss evil enough to have been behind the misery in at least two fighting franchises (possibly three if you count KoF). See, not only did he murder the Bogard bros' dad, he was also ordered the kidnapping of sweet lil' Yuri and the corruption of her father, Takuma, in the Art of Fighting series. That's right, he ordered Mr. Big and Mr. Karate around. He was a boss of bosses!
Geese started these injustices while he was still Southtown's youngest police commissioner, mind you - ten years before he started causing all sorts of problems with his corrupt King of Fighters tournament - so give him credit for being a multi-decade jerkhole. Exuding that right kind of Trump-ian evil business charisma, he's the boss SNK players love to hate the most. We can almost scientifically prove that fact because he's been killed off in Fatal Fury twice and, due to fan demand, the games kept revealing that he'd somehow survived multiple plunges off high-rise skyscrapers. Hell, even when they finally had to admit he was dead in the later games, for sure, they still brought him back anyway as the ghostly "Nightmare Geese" (and with a halo he definitely didn't deserve).
3. Jedah (Darkstalkers 3: Vampire Savior)
As far as wicked, world-conquering schemes go, traveling back to the dawn of time to turn the fetus of GOD into a vampire is way, WAY up there. We're talking about thinking so far outside the box that the very notion of the box becomes a hazy abstraction. Jedah gets +10,000 XP on cleverness alone.
He's also a pretty dapper reaper, wearing what looks like a modified high-school boy's uniform/muscle suit with enough confidence that the ensemble actually seems... fashionable? If you're going to pervert all of existence, may as well do it in style, no? Jedah catches the eye in a game that's already absolutely bursting with insane characters and outlandish settings: a showboating darkstar even among the underworld's best and brightest (worst and shadiest?).
Furthermore, Jedah applies an extra sanguine panache to his specials, being gross enough to use his bodily fluids as weapons. It's not enough for the shinigami hipster to shoot enormous, spinning saw-blades at you - no, he'll also blast you with his own blood in attack which might as well be called "Hepatitis Hose!" Oh, and he also steals your soul with a legally and physically binding "blood contract" that's really just a giant piece of paper he slams opponents onto using his own prehensile red stuff.
Killer fashion sense and killer blood. Jedah is the full package, ladies.
2. Heihachi Mishima (Tekken)
As mentioned previously, the halls of fighting game history might as well have a whole executive board staffed with evil businessmen moonlighting as evil karate champions (see: Wolfgang Krauser, Rugal Bernstein, et al). However, how many were sinister enough to toss their own flesh and blood into a volcano? And on multiple occasions?!
The story of the Tekken games revolves around the cycle of betrayal and burning Oedipal fury that turns the Mishima family tree. At first, it seems like an open-and-shut case of payback: Heihachi's son, Kazuya, gets revenge for the aforementioned volcano drop-off. Lesson learned, right? Nah, the man with the electrified bald spot never mends his ways and, over each subsequent game, he commits new acts of familial injustice which make the lava dunk into just one crime in a sequence. Not only did Heihachi toss his son into the fire, he also...
...locked his father, Jinpachi, underneath a mountain for decades.
...terrorized his illegitimate grandson, Jin, until he became a winged demon.
...spurned his adopted son, Lee, enough that he developed a garish split personality.
...and totally forgot about fathering an illegitimate son, Lars, until the bastard confronted him!
And that's all discounting the countless crimes Heihachi's Mishima Zaibatsu has committed upon innocents he wasn't related to. It also excludes the numerous atrocities of fashion the man has committed (seriously, it takes special arrogance for a boss to rock a handlebar 'stache and a diaper individually, let alone both together).
1. Akuma (Super Street Fighter II Turbo)
Put it this way - this guy introduced himself to the fighting game community by effortlessly beating the shit out of the boss you were scheduled to duel with. Few experiences from the pre-Internet video-game era made as striking an impression as the time Akuma literally just glided in, murdered M. Bison in a blink, and challenged you, the player, to a real fight. Here is a boss so bad, other bosses fear him.
Even though Akuma's inclusion in any Capcom fighter is just a given these days (playable with the flimsiest "codes" sometimes, too), and even after Capcom utterly nerfed his stamina in the name of "balance," there is still a visceral novelty to playing against him. This badass is what Ryu would be like if he stopped being a baby and started embracing the forbidden Dark Hadou fully!
Lets not forget that his signature move is the "Raging Demon," or "INSTANT HELL MURDER!" It's been about twenty years since the debut of this bastard sometimes known as Gouki, and there is still nothing more insulting/upsetting/decisive than getting demon-ed at the end of the round. The flames, the symbol, the iconic pose... it's like a week's worth of swirlies crammed into three or four horrible seconds.