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Let's face it, we all wanted to be the bad guy at one point. Quite honestly, most videogames do allow you to be the bad guy, repercussions or not, but sometimes you need more. You need to at least pretend for a little while that you are one insane, calculating motherfucker. You need to be a swaggalicious James Bond megalomaniac, a card-holding master planner with a side of asskicking. Sometimes, you just need to be Ledger Joker. And there really isn't any explicitly named simulator for that. Note, I did say "Batman Villain", so explicitly/overly super-powered villain games are out of the question. That is neither the spirit nor the presence of the experience I'm thinking of right now. I'll just put up a list in no particular order and talk for a while about each one.

1. Payday 2

It's a very supervillain-ey game. You get to extensively plan and strategize epic crimes and commit them like a true professional, all while wearing your favorite clown mask. That's all there really is to it. Fast-paced action, gang wars and inter-criminal intrigue, 80 different kinds of SWAT guy for you to shoot, and loads of weapons and playstyles to go about doing it all with. Very fun to do with teamwork, and very intense. Even though it's an excellent game, I do think it's probably the weakest supervillain simulator out of this list simply because there isn't that much variety in what you do.

The Payday guys are thieves and robbers, plain and simple. Their goal is purely the dollar, and their mastermind is too gritty and grizzled and (relatively) down-to-earth to consider things like terrorism, serial murder, and other methods of unleashing your inner-asshole on the computer-generated cityfolk. You can rob people, take hostages, and occassionally commit crime while you're at it.

2. Fallout New Vegas

Honestly, this only gets on this list because of the IEDs, the horrible atrocities you're free to commit, including but not limitted to paying a claw-handed metal monstrosity to tear your anoose with his blocky laserfists. That thing was NOT made for bedroom purposes. You do get to beat on your useless mooks, too, depending on how worthless and loyal they are. Oh, and you can conquer a city and make master plans, too, so there's that.

3. GTA V

When you're talking about a crime simulator, obviously the newest, biggest, shiniest one is the first to be brought up. With the amount of shit you can do in it, it's actually pretty fitting. There's a helluva lot of customization, everything from tights to makeup to masks, you're probably able to look like a bonafide supervillain, or at least some bad guy out of a spy movie, not that long into your multiplayer experience. It takes place in a satirical, backwards city full of murderable citizens, features all manner of heists for the seasoned machiavellian bastard, and it features a wide array of weapons with which to do all manner of dirty deeds, whether your deeds are as silver-age and simple as stealing the city's supply of fire trucks in order to utterly barricade the big highway, or as elaborate and difficult a scheme as stealing a tank from the military base...

There's also a lot of cool stuff you can do that isn't necessarily crime-related. Fancy cars, buying your own crib/base of operations, all the perquisites of screwing everyone over to get to the top, at your fingertips. If I'm not mistaken, you can even play golf and tennis with your fellow ill-moralled aristocrats. I mean, sure, you can be the typical terrorist type and say that you were doing it for an ideal or some shit, but that's probably because the game never included a simulator for expensive hobbies like sky-diving, part-time pilotting, golfing, sportscar-collecting, mansion-living, heading off to the parks with your gun and ATV to start hunting the most dangerous game of all. Y'know, the sort of lifetime benefits that criminal masterminds commit crimes for!

I guess the big downsides come from it trying to do too many things at once, and the fact that, no matter how good you are at things, unless it's flying, nothing changes very much. The animations are all the same, and everything stays clunky and stupid-looking. Even professional bludgeoners and knife-fighters swing their shit as half-assedly as someone with no idea what they're fucking doing.

YOU DON'T SWING A TRENCH KNIFE WHEN YOU WANT TO KILL A MAN WITH IT, YOU ASSHAT! WHAT THE FUCK ARE YOU WASTING ALL THOSE ANIMATION FRAMES FOR!? OH, LOOK, NOW YOU'RE DEAD BECAUSE THE POINTY END TAKES SHORTER TO STAB WITH. WHO'DA THUNK IT, RIGHT, SHITFORBRAINS!?

YOU KNOW ALL THOSE HOURS I SPENT MAKING YOU SUCKER-PUNCH HOARDS PEOPLE AND SUBSEQUENTLY GETTING BEAT TO DEATH BY THE COPS!? YOU KNOW THAT STAT THAT I SPENT BUILDING FOR HOURS AND HOURS SO THAT YOU COULD SERIOUSLY REK MOTHERFUCKERS BY HITTING THEM!? WHY THE FUCK ARE YOU STILL JUST SHOVING PEOPLE, YOU RETARD!? YOU'RE SUPPOSED TO EMULATE A LEARNING HUMAN BEING, SURELY YOU HAVE ENOUGH EXPERIENCE IN GRIEVOUS BODILY HARM BY NOW TO KNOW THAT SHOVING IS TACTICALLY USELESS BY THE FUCKING MECHANICS OF THE FUCKING GAME!? HOW THE FUCK DOES JIMMY GREENHORN KNOW HOW TO RELOAD JUST AS FAST AS SOMEONE WITH "MILITARY TRAINING"!? HELL, WHY IS THE ONLY THING THAT CHANGES THE TARGETTING RETICULE? THEY BOTH HOLD THE GUN THE EXACT SAME FUCKING WAY! HOW DOES THE PISTOL HAVE THAT MUCH SPREAD!? IS THIS WHAT ROCKSTAR THINKS AMERICANS ARE LIKE!?

Essentially, it's a pretty accurate representation of the ends of supervillainy, but half the means look like they were executed only by accident and not efficacy. Well, and the multiplayer leaves open the opportunity for an equally eccentric vigilante archnemesis, so there's two ups and one down.

4: Saints Row 2

This one has the advantage of them sweet Rich Supervillain Perquisites in the form of fancy-ass airport apartments with stripper poles, extensive character customization, (From what fighting style floats your boat, to the character's voice, to their very fucking walking style) and henchmen that aren't as completely useless as they usually are. Plus, with the addition of perks and upgrades, you can make armored, pimped-out supercars with chariot spikes and extended nitro boosts to commit crimes in style, and even increase your physical badassitude to Bane-like levels. You can war with other gangs and conquer territory, take hits out on people, raid supplies, take over casinos and strip clubs, nab drugs, and do all the things necessary for the establishment and upkeep of a proper supervillain empire.

While there aren't quite as many weapon options as there are in GTA, they stray from branching off into 800 distinct guns and get more into things like Pimp-cane shotguns, flamethrowers, and fucking samurai swords, and they move and use items like they know what they're doing. The world outside of crime isn't that well-developed, but you can create your own colorful sociopath and commit atrocities in the name of your criminal empire, so there isn't too much to be upset about.

They also have plenty of dynamic crimes that you can commit in the overworld without needing missions, which, afaik, you can't really do in GTA. You can kidnap hostages, rob stores, pedestrians, and hobos alike, and use people as shields, for those of you who need variety on the fly, free of cutscenes.

Any thoughts on this? Do you have any favorite games that you think can effectively capture the SuperEvilBoss feel?

EDIT: Dear god, I will never be hired for a job at this rate...

The Infamous series has a very good supervillain-ey feel to the entire series. I'm sure you're familiar with the game series, but this is by far my favorite game series that allows you to be the bad guy. Namely, Infamous 2.

I do disagree with a lot of the villainous options in the Infamous series, on the basis that the choices have no real meaning and substance to them. You either do the average thing or go out of your way to be a twat. That's not what villainy is about! Villainy is about making an easy road to the top by paving it with the ill-obtained labors and bloodshed of other people. Granted, the evil choices did exploit people, but it only ever reached the same mission conclusion, and we received a bunch of morality-swapped missions and cutscene that were similar in nature, because the lightning guy decided to go do something dickish out of the blue instead of just doing the regular, easy thing that didn't light fires under the feet of innocent children.

And as awesome as draining people to death and stuff always was, I just don't get the same Magnificent Bastard feeling when I play someone with powers of that caliber. It could easily be fixed if the writers went more in-depth with the details, buildup, and interaction with the plots and schemes the villain version of you would be doing rather than the big socio-political cluster fuck about the mutants and the anti-mutants.

Then again, if they did something like that just to make the puppy-punching path less ridiculous, they'd probably end up with a sad case of Dishonored syndrome, where you have to sacrifice your experience of the content to get the good ending.

Ohh, right, Dishonored! I knew I was missing a supervillain game! I was trying to avoid big superpowers, though, I guess, but superpowers do have a broader gameplay appeal.

The big problem I had with Infamous is it kept making the good guy endings canon. The game is called Infamous, seems like it should be making the "evil" endings canon.

Everyone always assumes that the good endings are the only good endings, so developers are alwas inclined to make their character be the good guy through sequels as a sort of "reward"... Because god knows, the writing just isn't good enough for bwing good to be its own reward, unless being evil is a ridiculous task done for little to no rEason and/or mechanicqlly more difficult... After all, if you don't walk away from a game with a warm and fuzzy feeling afterward, it's not a video game, it's a filthy communist manifesto that hates america!

Just stick your dick in an anthill, should suffice.

Also go fuck yourself.

I totally understand your point. The story is quite lacking, and the choices didn't make much difference to the storyline. But damn, was killing everybody with lightning so much fun!

Some of the older games had a lot of opportunities for super villainy, like the first two Geneforge games, Arcanum, the old Fallouts, Planescape Torment, etc.

Red Dead Redemption.

I dunno, the main story sort of takes you out of feeling like a villain. In fact whenever I did do anything really villainous in between missions, it sort of felt slightly out of character since he's supposed to be reforming and all.

Mainly was just referring to the many uses of the Lasso, tbh.

Hangings, Carlos-Style dragged along at high speeds murder, classic tied up damsel on the train tracks murder (while twirling your evil mustache, optionally).

And who could forget all the fucked up sidequests? Flowers for a dead woman, digging up corpses, other generally evil things.

But the most evil of all?

Cheating at high-stakes poker.

Another thing you could do with the lasso is drag them so they hang over a cliff and they'd slowly choke to death. Or just tie someone up and throw them in the water so they would drown.

Always thought you should have been able to rob a train in the game.

... You can.

Bound By Flame: Not a particularly good game, but fun enough. Being evil maximizes the most powerful skill tree in game and I do quite enjoy the PC's evolution into a horrible, fiery demon. Game DOES have some nice music on occasion and 1 very nice monster design (It's reveal has pretty good music too) but the writing is horrid and everyone is a sarcastic douche. Still was fun. 

http://store.steampowered.com/app/243930/

Overlord: Raising Hell: God I love that game... You can be a benevolent overlord (within reason) but that's no fun. I much prefer kicking people's heads in and razing ransacking their houses. Plays a bit like Pikmin if you're familiar with that, but the theme is way better (well obviously). Didn't enjoy the second game that much, which was a shame. Oh well...

http://store.steampowered.com/app/12710/

Some Browser Games I Enjoyed (These you can do at work, so you don't have to worry about unemployment):

I Am An Insane Rouge AI: GLaDOS Sim, anyone?

http://www.kongregate.com/games/nerdook/i-am-an-insane-rogue-ai

Mastermind: World Conqueror: Probably the most SUPER-villiany ala James Bond experience I've ever had in a video game. While the novelty lasts, I found it to be pretty fun. Gets repetitive after a while tho.

http://www.kongregate.com/games/theswain/mastermind-world-conquerer

Destroy all Humans was probably one of the first villainy games that raised your adrenaline depending on how much army you could get on you.

It’s been suggested that the old video game Paperboy had you playing as a villain protagonist.

You’re delivering papers to customers and getting points for breaking non-customers windows (and vandalism in general, along with assault on citizens). If anyone unsubscribes, they become fair game until they resubscribe again.

Obviously, you’re running some sort of racket.

Not supervillainy level, but still pretty fun.

KotoR provides an excellent Sith Lord experience. 

I enjoyed having Zalbaar kill Mission for me.

Hotline Miami would be more of a violent vigilante game. It's a indie, 2D top down action produced in 2012 by Dennaton Games. There's not much of a plot in the first game but instead, more focused on action and sweet sweet blood. 

If you've played Payday 2... you've definitely heard of this game before. I mean... here's a DLC trailer that links HM to Payday.

I can't say that I prefer the sequel over the original, because I don't. However, I recommend that you blow all your money both games. Gameplay is pretty much the same in both games, storyline is more developed in the second game but I beg you to start the first game.  Here's a trailer of the second game.

WARNING: Don't play unless you want to rage your balls off. 'Cause that's gonna happen.

Tried to do a no death run on the first game. Got to the final boss, then died because I killed the panthers behind the fountain and ninja bitch threw a knife at me. I then cried for twenty minutes.

Anyway, that's one of my favorite games of all time. Didn't care much for the second one, but it had some sweet music (namely Roller Mobster, Run, and She Swallowed Burning Coals). I think the thing I remember most about that game is the music. And also how mind-numbingly hard it is (specifically the second one, what with its open areas where enemies that are off-screen shoot you and shit).

Also planned on going as Jacket for Halloween, but I'm broke so I couldn't buy a rooster mask and a letterman jacket.

Anyway, as for good villain experiences, the KoTOR games, as Malk said, both provide nice Sith Lord experiences. The first half of the Force Unleashed too, but then you became a good guy. But you can become a Darth Vader rip-off if you go for the bad ending.