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After losing the match, the bet was settled and Sibi/Ivy got her prize as settled before. 
Not that the big bad wolf was actually unhappy of the defeat.

sibi_the_messtress bandai_namco mythology soul_calibur soulcalibur soulcalibur_iv ivy_valentine sibi_(sibi_the_messtress) canid canine canis domestic_cat felid feline felis maine_coon mammal mythological_canine mythological_creature werecanid werecanine werecreature werewolf wolf anthro anthro_penetrated armor bdsm bodily_fluids bondage bound clothing cosplay cum cum_from_pussy cum_in_pussy cum_inside dominant dominant_female dominatrix duo female female_penetrated fingers game_over game_over_screen gameplay_mechanics genital_fluids genitals gui health_bar inaccurate_knotting knot knotting leaking_cum looking_pleasured lore male male/female male_penetrating male_penetrating_female melee_weapon narrowed_eyes penetration penile penile_penetration penis_in_pussy pussy rape_play seductive sex size_difference small_dom_big_sub strangling sword teeth text tongue torn_clothing vaginal vaginal_penetration weapon whip 1:1 2024 absurd_res digital_media_(artwork) hi_res url rating:e

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lintwave soulcalibur amani_(amanimynt) canid canine canis mammal wolf anthro clothed clothing cosplay crossdressing dress fishnet_clothing fishnet_legwear flower fur gloves green_body green_fur handwear legwear male melee_weapon plant rapier red_background rose_(flower) simple_background solo sword weapon yellow_eyes rating:s

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Villianous

Definitely one of the biggest projects I've worked on. The goal was to draw 50 different video game villians, and only 1 villian per franchise (With one exception). I appologize if some of the art isn't exactly up to snuff, as this has been a work in progress for almost a year and a lot of the characters were already done months ago.

I'll now list each character for those who don't recognize everyone and give them a little bio.

1. Andross
First appearance: Star Fox (SNES)
Most Recent Appearance: Starfox Adventures (GCN)

Andross was once a brilliant scientist, but was banished to the Planet Venom after an experiment goes haywire. This guy is power hungry and totally nuts! Usually appears as a giant floating head with two hands. He is the mortal enemy of Fox McCloud.

2. Black Bomberman
First Appearance: Bomberman II (NES)
Most Recent Appearance: Bomberman Live (Xbox Live Arcade)

In Bomberman II, the original Bomberman gets framed for a crime he didn't commit. His first look-alike, Black Bomberman robs a bank and leaves Bomberman to take the fall. Although originally portrayed as a villian, and later a smooth talking rival, Black Bomberman joins the ranks of "Villians that become Good Guys" as he's not only become playable in multiplayer options but sometimes flys Bomberman's ship for him. Wait, when did Bomberman get a ship?

3. Black Shadow
First Appearance: F-Zero X (N64)
Most Recent Appearance: F-Zero Climax (GBA)

Black Shadow is the servent of Deathborne and just loves antagonizing Captain Falcon, of whom he is one of his many rivals. His biggest role so far is his anime role, of which he remains the most prominent threat to Captain Falcon. He is also heavily emphasized in GX for the Gamecube, although he is not usually the final boss in any of the games.

4. Bowser
First Appearance: Super Mario Bros (NES)
Most Recent Appearance: Super Mario Galaxy (Wii)

Here's a guy who needs no introduction. You get bonus villian points for being the main antagonist of the most famous video game mascot in history! Bowser gets props just for the sheer number of games he's been in, he also proves he can be just as durable as his mustachioed rival by appearing in party, racing, fighting, and even sports games.

5. Captain Syrup

First Appearance: Wario Land: Super Mario Land 3 (Gameboy)
Most Recent Appearance: Wario Land 2 (Gameboy Colour)

Captain Syrup is the leader of the Brown Suger Pirates, and Wario's first real nemesis. Like Samus Aran, Captain Syrup's gender was swapped during english translation and thus many people were shocked to find that the captain was in fact a woman. She's ruthless and just loves treasure, but then again so does Wario. See where things get complicated now?

6. Carmen Sandiego

First Appearance: Where in the World is Carmen Sandiego? (PC)
Most Recent Appearance: Carmen Sandiego: The Secret of the Stolen Drums (Xbox, GCN, PS2)

No doubt you've heard of her, that sticky fingered filcher Carmen is craftier than a macaroni picture. But whether you recognize the name from the television show or the geographical edutainment game the series is number one in it's genre. But with stuff like "Mario is Missing" to compete against, that's not really a hard thing to do. Nevertheless, Carmen herself is super famous.

7. CATS

First And Only Appearance: Zero Wing (Sega Mega Drive)

ALL YOUR BASE ARE BELONG TO US.

8. Dark Queen

First Appearance: Battletoads (NES)
Most Recent Appearance: Super Battletoads (Arcade)

Most often she is portrayed as a dark, mysterious, sex goddess. She wants to rule the universe and all that good stuff, but the Battletoads keep getting in the way. She also commands giant rats... yeah.

9. King Dedede

First Appearance: Kirby's Dreamland (Gameboy)
Most Recent Appearance: Kirby Squeek Squad (DS)

Hail to the king baby! The only thing Dedede loves more than antagonizing that little fluffball Kirby is making his subjects miserable. He's pretty self centered and doesn't care if his people go without food, after all it's all about him right? However he has been known to be good at times, so he isn't completely evil. He's even saves the world every so often, when it suits him that is.

10. Duck Hunt Dog

First And Only Appearance: Duck Hunt (NES)

I swear this thing must be evil or something, why else would he constantly mock you every time you screw up? He's the first villian on the list that hasn't actually done anything evil, but his cackle will haunt my dreams forever.

11. Donkey Kong

First Appearance: Donkey Kong (Arcade)
Most Recent Appearance: Donkey Kong 3 (Arcade)

The original Donkey Kong only lasted a few games, but what happened to him? Well rumour has it that because him and his family were constantly being harassed by Mario the only option he had left was to enter the Witness Protections Group. He now lives peacefully in a jungle somewhere under a new name, free of any plumbers. But that doesn't mean we can't remember Nintendo's first ever villian, it'd be a paltry list without him.

12. Dracula
First Appearance: Castlevania (NES)
Most Recent Appearance: Castlevania: The Dracula X Chronicles (PSP)

Not only is Dracula the most famous monster of all time, he's also one of the most famous Video Game Villians of all time. He has a penchant for blood, and he's one of the most persistant villians on the list. Continuously re-animating yourself just to harass the same family generation after generation, man this guy's hardcore.

13. Miles Edgeworth

First Appearance: Phoenix Wright: Ace Attorney (DS)
Most Recent Appearance: Phoenix Wright Ace Attorney: Trials And Tribulations (DS)

Once an ambitious youngster, Miles Edgeworth's life changed after a terrible accident. Now one of the most feared prosecuters in the world, he rules the court with an iron fist. Until of course, spikey haired Phoenix Wright enters the courtroom. Edgeworth is cool, calculating, and smug, and all of these things make you want to beat the snot out of him. Prime villian qualities there!

14. Dr. Eggman

First Appearance: Sonic The Hedgehog (Genesis)
Most Recent Appearance: Sonic Rush Adventure (DS)

Here's another classic, Dr. Eggman is a genius at robotics but he can get pretty tempermental and throw a fit at the slightest miscalculation. One thing's for sure, anyone who captures poor defenseless little animals and traps them in robots while they slowly have their life drained away in order to power said robots, has a serious problem. Maybe he was attacked by animals as a kid and this is his way of getting some kind of revenge? Or maybe he's just an ass.

15. Emperor Bulblax

First And Only Appearance: Pikmin (GCN)

I know he looks small, but when you're the size of a quarter, you'll see how important perspective is. Emperor Bulblax is the final boss of the game Pikmin. I'm not exactly sure what he's supposed to be, but he's pretty gross. Touching everything with that big old tongue of his. It takes a while before you actually chisle his health down to nothing but is it actually worth it in the end? The treasure he holds isn't actually needed to beat the game, and when your appearance is only optional it kinda hurts your Villian Score.

16. Ganondorf

First Appearance: The Legend of Zelda (NES)
Most Recent Appearance: The Legend of Zelda: The Twilight Princess (GCN, Wii)

Ganondorf is the embodiment of evil. He's taken many forms, from giant beast to unholy essance, but in the begining he was a man. A man with an endless thirst for power, and even though he is defeated at the end of each game he will always return. What makes him so terrifying is that he will never actually die, and he's cruel and ruthless enough to place among the top of the list of Greatest Video Game Villians of all time.

17. General Morden

First Appearance: Metal Slug (Arcade)
Most Recent Appearance: Metal Slug 6 (Arcade)

How many of you took a look at him and immediately thought of Saddam Husain? I'm sure the resemblance was more than a coincidence. General Morden is your typical war mongering general, but unlike most generals I know of he often sides with aliens. It's pretty embarassing though when those same aliens continuously betray you as well. General Morden can often be seen hanging from something very high in his boxer shorts.

18. Inky

First Appearance: Pac-Man (Arcade)
Most Recent Appearance: Pac-Man Championship Edition (Xbox Live Arcade)

The blue ghost from Pac-Man.

19. Blinky

First Appearance: Pac-Man (Arcade)
Most Recent Appearance: Pac-Man Championship Edition (Xbox Live Arcade)

The red ghost from Pac-Man.

20.Pinky

First Appearance: Pac-Man (Arcade)
Most Recent Appearance: Pac-Man Championship Edition (Xbox Live Arcade)

The pink ghost from Pac-Man.

21. Clyde

First Appearance: Pac-Man (Arcade)
Most Recent Appearance: Pac-Man Championship Edition (Xbox Live Arcade)

The orange ghost from Pac-Man.

22. Grumple Gromit

First Appearance: Bubble Bobble (Arcade)
Most Recent Appearance: Puzzle Bobble 2 (Arcade)

His Japanese name is "Super Drunk". That's fucking awesome.

23. Gruntilda

First Appearance: Banjo Kazooie (N64)
Most Recent Appearance: Banjo Pilot (GBA)

This girl must have a lot of time, because she always speaks in rhyme. Another villian on the pile, this one's gross her face is vile. The ring came off my pudding can, "Take this pen knife my good man!" Man this schtick is getting old, Stop & Swop was a flop, or so I was told.

24. Inferno

First Appearance: Soul Edge (Arcade)
Most Recent Appearance: Soul Calibur II (PS2, GCN, Xbox)

Inferno is the very embodiment of Soul Edge itself, retaining the memories of every warrior who fought with it, it is able to mimick their abilities and fighting style. It appears as a skeleton engulfed in flames, and it feeds off of souls. Inferno was the last boss in the first few games, but was later replaced by Abyss.

25. Jack of Blades

First Appearance: Fable (Microsoft Windows, Xbox)
Most Recent Appearance: Fable: The Lost Chapters (Microsoft Windows, Xbox)

Jack of Blades was once known as the strongest hero of all time, but considering what kind of list he's on right now I think you can guess how that turns out. As it happens, Jack is the reason everything bad happens to you and he's really evil and probably eats babies, he turns into a dragon at the end and after killing him you're given the option to either banish his magical mask (Which houses his soul) or keep it, thereby becoming the new "Of Blades".

26. King K. Rool

First Appearance: Donkey Kong Country (SNES)
Most Recent Appearance: Donkey Kong Barrel Blast (Wii)

This guy wrote the book on insanity, he concocts plans to steal, blow up, or conquer anything and EVERYTHING. And all for no real reason so it seems. You know you're a villian when you steal someone's major source of food entirely because of spite, and then blow up their island for some laughs. Recently he's tryed conquering other planets as well, you gotta at least applaud his efforts. K. Rool also changes jobs more than Mario does, he's been king, pirate captain, scientist, and boxing heavyweight. He must have Multiple Personality Disorder or something.

27. Kefka

First Appearance: Final Fantasy VI (III in North America) (SNES)
Most Recent Appearance: Final Fantasy VI Advance (GBA)

Known for two things among Final Fantasy fans, the first being that Kefka is known as one of the most evil characters the series has ever known. The second is that unlike the series' staples Kefka is not only the main antagonist but also mortal. Kefka's human side made him more distinguishable from other series villians and overall a better character. Very endrogenous, Kefka insists on dressing as a clown.

28. Kratos

First Appearance: God of War (PS2)
Most Recent Appearance: God of War II (PS2)

Definitely the black sheep, Kratos is the only protagonist on the list, but that in no way makes him a good person. Kratos was best known for killing, and he was damn good at it. Once a captain of the noble Spartan army, Kratos' life of infamy began. After calling upon Ares the God of War for aid in battle he gave his life to the gods. He becomes a servant to Ares, but eventually repents and instead sets out to make him pay for all the sins he forced Kratos to commit. Kratos is in this way, a tragic hero.

29. LeChuck

First Appearance: The Secret of Monkey Island (Amiga)
Most Recent Appearance: Escape From Monkey Island (Macintosh, Microsoft Windows, PS2)

LeChuck is an evil-undead-zombie-demon-ghost-pirate and scourge of the seven seas, when he isn't trying to force Elaine Marley to marry him he's engaging in an insult duel with Guybrush Threepwood. Captain Barbo- er, I mean LeChuck is another one of those villians that become good guys at points in the series.

30. M. Bison

First Appearance: Street Fighter II (Arcade)
Most Recent Appearance: Super Street Fighter II HD (Xbox 360, PS3)

M. Bison was one bad dude, and a recouring villian in the Street Fighter II franchise (I'm gonna list Street Fighter II as it's own franchise because it's STILL releasing games). You actually got to play as him in Street Fighter II: Turbo, and that was cool... for about five minutes. Afterwards you just went back to using E. Honda and spammed the Thousand Hand Technique. Also he was played by Raúl Juliá in the movie. Awesome...

31. Master Hand

First Appearance: Super Smash Bros. (N64)
Most Recent Appearance: Kirby and the Amazing Mirror (GBA)

Master Hand symbolizes the player and everything they do. He pulls Nintendo characters out of The Chest of Time and places them into stadiums and forces them to fight each other. Why he does this is anybody's guess, but if it's just for the purpose of amusing himself that would make him one evil dude.

32. Medusa

First And Only Appearance: Kid Icarus (NES)

Some freaked out bitch with snakes for hair, was turned into a monster for ruining crops. Srsly. She's the last boss in the game, and despite how different she looks in the manual she's a giant head in the game.

33. Mewtwo

First Appearance: Poke'mon Red and Blue Version (Gameboy)
Most Recent Appearance: Poke'mon Fire Red and Leaf Green (GBA)

Mewtwo is a clone of the Poke'mon Mew, and the last Poke'mon you face off against in the game. He's also the strongest Poke'mon in the series... well except for Mew... and Celebi is also pretty strong...

...Jirachi, Deoxys, Darkrai...

...Actually nevermind...

34. Mike Tyson

First and Only Appearance: Mike Tyson's Punch-Out!! (NES)

You know who he is, "Kid Dynamite" himself once starred in a video game. Although after Nintendo lost the liscence for his name Punch-Out was re-released, and Mike himself was replaced by the significantly less cool "Mr. Dream". My Uncle works at Nintendo, and he said if you beat the game in less than 10 minutes you get to see a secret ending where Tyson bites off your ear!

35. Murai

First Appearance: Ninja Gaiden (Xbox)
Most Recent Appearance: Ninja Gaiden Sigma (PS3)

I honestly know very little about this guy. Apparently he's some ninja dude with nunchucks, I did him as a personal request. Go look him up on Wikipedia if you really want to know about him.

36. Doctor Neo Cortex

First Appearance: Crash Bandicoot (PS1)
Most Recent Appearance: Crash of the Titans (Wii)

Doctor Neo Cortex is very twisted and manipulative and, like almost every other video game villian, a mad scientist. The appeal of Cortex comes mostly from Naughty Dog's cleverly written stories, and as such Doctor Neo Cortex reflects the game's hillarity well. His stereotypical occupation and character traits seem to almost parody villianous mad doctors as a whole.

37. Pokey Minch

First Appearance: Mother 2 (Earthbound in North America) (SNES)
Most Recent Appearance: Mother 3 (GBA)

Pokey is Ness' neighbour, but it is apparent that he harbours a grudge against his family. Pokey seems like your average pig-faced little boy at first, but he in fact assists Giygas in taking over the world. He doesn't seem like the type of person who was born evil, but probably just sides with the winning team, like Wario.

38. Professor Pester

First And Only Appearance: Viva Piñata (Xbox 360)

This guy has got to be one of the biggest douchebags in the entire world of video games, not only because he acts like one whenever he enters your garden. Once he pulls out that long piece of wood, you know what's about to happen, and it's not going to be good. After spending countless hours of attention and effort on your precious local piñatas, Professor Pester will have no qualms with forcing you two to "part ways" if you know what I mean. What an asshole.

39. Psycrow

First Appearance: Earthworm Jim (Genesis)
Most Recent Appearance: Earthworm Jim 3D (N64, PC)

Just as his name implies, this guy is a psycho! This crazy-ass spacesuit wearing bounty hunting crow will chase Earthworm Jim all over the galaxy just to get his super suit back for his boss, Queen-Slug-For-A-Butt.

40. Pyramid Head

First Appearance: Silent Hill 2 (PS2)
Most Recent Appearance: Silent Hill: The Arcade (Arcade)

Pyramid Head knows what raping people is about. He knows how people are supposed to be raped. Anyone who doesn't rape by the rules of wavedashing, no items, and Final Destination is a scrub.

41. Rabbid

First And Only Appearance: Rayman Raving Rabbids (Every fucking system this gen and last)

Bunnies that want to take over the world.
WAAAAAAAAAARGHH!!

42. Revolver Ocelot

First Appearance: Metal Gear Solid (PS1)
Most Recent Appearance: Metal Gear Solid: Portable Ops (PSP)

Revolver Ocelot holds the record for longest time spent twirling his guns, and he wasn't even trying. The only thing he loves more than twirling his guns is torture. Revolver Ocelot is a great villian, because no matter what the outcome he always seems to come out on top at the end of every game. Plus, GUN TWIRLING!

43. Ridley

First Appearance: Metroid (NES)
Most Recent Appearance: Metroid Prime 3: Corruption (Wii)

Ridley has appeared in almost as many games as Samus herself, and can best be described as the Metroid series' main antagonist. Despite looking like a savagte beast, Ridley is actually extremely intelligent and can command the Space Pirate army. He is the perfect combination of brains and brawn.

44. Scorpion

First Appearance: Mortal Kombat (Arcade)
Most Recent Appearance: Mortal Kombat: Armageddon (PS2)

Scorpion has appeared in almost every Mortal Kombat game ever made, and is probably the most well known character outside the games. His lines "Come here!" and "Get over here!" are iconic on their own right. Besides that, Scorpion is a ninja, and that's reason enough to make him a badass.

45. Space Invader

First Appearance: Space Invaders (Arcade)
Most Recent Appearance: Space Invaders DS (DS)

These guys would crawl down the screen in the game Space Invaders and you gotta shoot them down without getting yourself killed. If one of them reaches the bottom, it's game over.

46. Sturm

First Appearance: Advance Wars (GBA)
Most Recent Appearance: Advance Wars: Duel Strike (DS)

Sturm is the leader of Black Hole, and is supposedly from space. His Japanese name is German for Mr. Evil, he is awesome, and you should all love him.

47. Tom Nook

First Appearance: Animal Crossing (GCN)
Most Recent Appearance: Animal Crossing Wild World (DS)

This guy seems nice at first, but don't let his innocent demeanor fool you, he's pure evil. Do you have any idea how much he charges for a house?

48. Albert Wesker

First Appearance: Resident Evil (PS1)
Most Recent Appearance: Resident Evil 4 (GCN)

Cool and precise, Albert Wesker is definitely one creepy customer. His motives are never crystal clear. Whether he's working for or against Umbrella Corporation, Wesker always poses a threat. He's the kind of guy who will, and has, sacrifice his entire squad in order to protect his own interests. For that, he earns the title of asshole, and by association one of the top Video Game Villians. And that's an order.

49. Dr. Wily

First Appearance: Megaman (NES)
Most Recent Appearance: Megaman Powered Up (PSP)

The German robotics specialist, Dr. Wily is known for creating some of the most ridiculous and ineficient robots ever conceived. Why put all that knowledge to use and build a giant laser, or a boss room lined entirely with spikes when you can create "Topman"? If this proves one thing, it's that Dr. Wily is definitely one eccentric scientist.

50. Ze Professor

First Appearance: Conker's Bad Fur Day (N64)
Most Recent Appearance: Conker: Live and Reloaded (Xbox)

And yet another... German scientist. Ze Professor is the Great Fairy Panther King's top scientific mind, and also his advisor. Ze Professor created the Tediz, cyborb bears, and plans on using them to rule the world. He resents working under the King, and occasionally makes little remarks about him behind his back. Ze Professor is the mastermind behind such great inventions as the floating chocolate.

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