Top 10 Best Evil Bosses to Work For (and why it may be a bad idea)

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Top 10 Best Evil Bosses to Work For (and why it may be a bad idea)

In all walks of fiction, the hero usually travels alone, and at most has a small band of allies to follow along. Sometimes heroes band together and form teams, but rarely do they bulge beyond militia numbers. The villains, however, oh boy the villains. They are no strangers to having help. If the government wants to give out jobs, they need to release a few super criminals into the population. Tons of minion work will pop up. There’s a wide range of positions, really. Sure there is the grunt work, wet work stuff. But some villains operate on legit means. Plenty of opportunities to be had in a business run by people who are ambitious enough to want to rule the world. So I’ve compiled a list of the best villains to work for (and some reasons why you might want to keep a few extra resumes handy).

10. Monty Burns

Burns even relaxes classier than you do.

Why it would be great…

We’re all familiar with the face of corporate (and general) evil on the Simpsons. If ever there was a villain…well it would probably be Bart – the kid is a walking ad for abortion advocates. However, C. Montgomery Burns at least makes more money by being evil, and so of course has employees. Bart just has Milhouse, and nobody likes Milhouse. As if you didn’t know already, Burns runs Springfield’s main source of power, the nuclear power plant. Of the many employees that work there, one of them is the ever incompetant Homer Simpson. Think about it: Homer is borderline retarded, and the running joke of him working there is that all he does is goof off and nap, assuming he does show up. The show has almost forgotten the man even works there, only occasionally making a joke about how he will soon get fired or he hasn’t shown up for weeks. And yet he can always return to his job as a safety manager. You can be the worst employee ever and still get paid. It’s incredibly easy!

Why it might suck…

Homer Simpson is a special case, and yes that has more than the one meaning. Where Homer is constantly able to goof off and gain major promotions (only to lose them) and never show up and still keep his job, everyone else is extremely expendable. Burns has been known to fire people as a joke, to amuse himself during the long days. Now, Lenny and Carl have been fired a few times, and they were able to come back – but it may have something to do with their proximity to Homer. Frank Grimes was also very close to Homer, but he died because Homer’s immunity to consequences sent him over the edge. So if you are not naturally a lazy, stupid, best friend of Homer, this may not be the job for you.

Necessary Job Skills

  • Entry-level knowledge of what nuclear power is. (ex: What is nuclear power? That’s it.)
  • Acceptable degree of ignorance in order to tolerate less than excellent workers.
  • No women, ducks, or dogs. (We have enough of those.)

9. Number 2

Why it would be great…

You are 2 cool for school, Number 2.

Now while others on this list are the top of the food chain, Number 2 was…well the number 2, to Dr. Evil. Keep in mind, however, that Dr. Evil is only around for a few months between long, varying absences. The time he wasn’t around, Number Two ran the show, and he was fantastic at it. He increased productivity and profits ten fold. I’m sure with that comes extra employee benefits and pay, too. Plus, if you’re lucky, you get to work in a factory that makes miniature models…of factories. I’ll give you a moment to come down from that fantasy high.

Why it might suck…

Remember how Number 2 isn’t always in charge? Right, well that’s when Dr. Evil is back, and besides having the surname Evil, he’s also a tad incompetent. Not only that, he’s a satire of Bond villains. Which means that if you work for him in any illegal capacity, you’re going to die. If the hero doesn’t get you, you’ll probably be a test subject for whatever crazy death trap he has planned to use on said hero. And Number 2 wont be able to get you out of that jam.

Necessary Job Skills

  • Comfortable working with animals (that may or may not have laser beams attached to their heads).
  • Willing to relocate at a moment’s notice.
  • No strong ties to any British government agencies.
  • Ability to move out of the way of steam rollers.
  • Ability to guard a highly trained secret agent, solo.

8. Big Boss

The only time he's blue collared is when he's eating a blue berry pie.

Why it would be great…

You may not be as familiar with this employer as the others, so I’ll give a brief history. Big Boss is the big boss. The main crime lord in a city of the future. He commits crime, in a future time. He’s more of a desk criminal, however. White collar, quite literally. To do the dirty work, he has a team of loyal henchmen and women who carry out big heists. This all takes place in a world where cops are the main focus. So in other fiction, the minions are assumed to go to prison but we rarely ever see that. Here, we know for a fact that the criminals go to jail when caught. I mean, there can’t be any problem with due process because it’s not some vigilante catching them, it’s a cop. Granted it’s a cop with a robotic dog, but he earned that dog by rising through the police ranks. So how do you keep a show going if the criminals are always being “sentenced to jail”? Well, they get out. Simple as that. The only one who can really bust them out is Big Boss, posting bail and getting some dirty cops to help him out. I mean come on, this is a big city, and we only ever see a handful of super cops. There has to be lesser cops around, ones who are resentful that they aren’t made of metal, or get an awesome set of vehicles, or a fucking robot dog. So they take a little on the side from Big Boss to get back at ol’ Bulletproof, who they think only got his job not because he’s a trench coat wearing bad ass, but affirmative action.

Why it might suck…

The villains get their names almost on a Dick Tracy principle. The idea that your villain name is like a nick name, based on some personality trait or something eventful that happened to you. While most of the villains have passable names, if you were unlucky you might get stuck with Pencil Dick or Pizza Face. And that shit goes on your police record. Imagine going into work every day and hearing everyone call you Ratboy – and then you get arrested.

Necessary Job Skills

  • An interesting concept that helps to accent your specific skills (fat managerial types need not apply).
  • Willing to commit crime, in a future time (this is very important)
  • Must love cats.
  • Able to work with the differently-abled (like idiot nephews).
  • Must hate robot dogs.

7. Magneto

Why it would be great…

I chose the movie version for the pic because he looks far more fatherly than the muscle-bound guy screaming electricity in the comics.

Like Professor Xavier, Magneto wants to protect mutants from the hatred on them from humans. Where they differ, Magneto finds it easier to just wipe out all humans and let the gene pool just be all mutants. Magneto often comes across as very fatherly, being very protective of his “children” and making sure they grow up right and do what is best for their “family.” It’s part of what makes him such a great villain, that he’s not some Snidely Whiplash, but rather someone you could really see siding with. What’s more, the dude lives in a fucking asteroid. That’s cool shit right there, and you get to live up there with him. So you’re at the bar, and the “I can have sex with you 10 times before you even know it” line isn’t working. Just say you live on an asteroid and the bitches are all yours. Bitches love space.

Why it might suck…

Most people who are big into one cause are big into others. You think Magneto is only about the furthering of mutant cause? Hell no. He probably hates animal cruelty too. And he camps out in front of Wallstreet holding up 99% signs. The guy is a serial protestor, and you have been signed up to his team. Sure you sometimes get to go shoot lasers and fly into battle along side, and against, beautiful and scantily clad women, but Magneto knows that violence may be the answer, but not the only one. Enjoy throwing red paint on Xavier when he’s being wheeled out in his new fur coat.

Necessary Job Skills

  • Flight, laser-anything, control of something (bowels and self do not count), or any other “power” that most do not have.
  • Ability to die and come back a short time later (note: this does not count as your power).
  • Hair.
  • No fear of heights.

6. Cobra Commander

Commander being more of a dick than anything, but still evil.

Why it would be great…

Cobra, the big leagues. All other world problems are put on hold because Cobra is once again firing lasers and building weather devices and controlling our minds with rock and roll. You get to drive in cool vehicles, wear awesome uniforms, and shoot god damn lasers. Plus, you’re pretty sure that Baroness chick has been giving you bedroom eyes from behind her sexy Tina Fey glasses. Sure you’re going to war against a better funded military, and you’re usually going to lose each battle you’re in, but you’re going to have fun doing it. Why? Well, have you ever seen a Cobra member die? Sure, it may be implied, but if we operate on the assumption that death is only confirmed by a lifeless corpse, then Cobra is doing pretty well. Of course, those lasers do hurt, and they could blind you. So don’t stare directly at the Joes.

Why it might suck…

First Mexicans, then Indians, now this. We just can't win!

Okay, so there are two teams: Cobra and the Joes. On the Joes side, everyone gets a cool name and theme. Uniqueness is key, but team work is big too. It’s like being in a super extended version of the Village People, but there are actually a few women this time. Now, for Cobra, there are some members who have cool names and memorable looks, but only a few. The rest are grunts all with the same uniform and hardly a face to be shown. So Baroness might have been checking you out, but she honestly can’t tell you from that guy in accounting you hate. Plus, lasers sting more than paintballs. Also, if you happen to join Cobra as it stands now, with the 2011 reboot, you’ll find all the grunt work has been outsourced to these weird jell-o mold creatures. Sorry, mate.

Necessary Job Skills

  • Expert with blue lasers (red need not apply).
  • Able to wear a face-covering mask all day.
  • No U.S. citizenship is a big plus!
  • Knowledge (it’s half the battle).

5. Giovanni

The only thing keeping Pokemon from taking over is this man.

Why it would be great…

The mysterious leader of Team Rocket, Giovanni is also a gym leader and cat enthusiast. He’s also more manly than two bears fighting over a steak covered in Old Spice. He runs a legit front with his gym, and while I’m not sure exactly how a gym makes money, it doesn’t matter because he makes his most money by running Team Rocket. Team Rocket steals pokemon, pure and simple. They steal other things, too, sure, but the main goal is to help Giovanni collect rare and powerful pokemon. Team Rocket was also the first to do the whole stealing pokemon bit. Since then each generation has had its own “team” to fight against, but working for Rocket means you work with the first, and the best. You were into stealing pokemon before it was cool.

Why it might suck…

In any case, the company retreats are the best time you'll ever have.

It’s hard to really say why it would suck, or even why it would be that awesome. The reason is Giovanni works in the background as far as we know. In the anime, our main experience with Team Rocket is Jesse and James, two bumbling members who rarely speak of “the boss” but are still determined to steal this one and only Pikachu just for him. That’s dedication. This is either from fear or admiration of Giovanni, or perhaps just a great sense of perseverance, but either way the team is motivated beyond all belief. Still, Jesse and James are like the black sheep of this organization. When they encounter other members, they are doing so much better than they are, with much more funding and success. One can only assume that Giovanni is a really great boss if you’re competent and actually manage to steal pokemon. However, if you’re bad at it, as many grunts are in the games, he seems to mostly forget about you and in one case he even tried to have Jesse and James get killed upon a blimp he wanted destroyed for the insurance money. Also, Giovanni fucks with pokemon, like Mewtwo. If you ever sit down and read some of the pokemon facts, you’ll know that these creatures could easily destroy each and everyone one of us without a moment’s reprieve. Working with Giovanni can sometimes be like poking a bear with a bear hormone-laced salmon.

Necessary Job Skills

  • Able to work with a partner.
  • Willing to step aside when someone beats you in a pokemon battle (honorable trait).
  • Your own Rattatta, Raticate, Ekans, Arbok, Koffing, or Weezing (you may not use any other pokemon).
  • Willing to steal from children, but not hurt them in any way.

4. General Warhawk

"LET ME SHOW YOU INAPPROPIATE WORKPLACE TOUCHING!"

Why it would be great…

Another obscure choice, but trust me when I say it would be pretty sweet working for him. Sure he’s an asshole to most everyone he knows, and his schemes rarely work out, and you’re not exactly sure if that general rank was appointed or he just started calling himself that, but at least you wont die. Working for S.A.V.A.G.E. you are constantly at odds with the U.S. military, but in the show we really don’t see them take on the villains directly. Instead, they call in Rambo. That’s right, Rambo. Let’s clear something up first, though. This isn’t quite the Rambo from the movies. In fact, working for the U.S. military should be your first hint this isn’t the movie Rambo. While this version is certainly badass and dangerous, he doesn’t kill. He rarely fires a gun, and if he does it’s not directly at anyone with the intention to kill. While in Cobra you might assume death takes place, under Warhawk’s command it’s almost always clear that the goons aren’t being killed.

Why it might suck…

Also, you will probably have to answer to these assholes.

To compare to Cobra again, in Cobra if you lose, it’s not surprising. I mean, they have a whole army, just like Cobra does. It’s a pretty fair fight. With Warhawk, your only obstacle are the Forces of Freedom. But the rest of the members rarely do anything, it’s just Rambo. Sure you’re not as well trained as anyone on the U.S. side, but come on it’s one guy. He doesn’t even wear a shirt and he never comes out with a scrape. He’s either immortal or you’re really bad at shooting. Either way, you’re face is always going to be red when that small island village is liberated from Warhawk’s rule.

Necessary Job Skills

  • Knowledge of how to operate a wide variety of guns (perfect aim is not a must).
  • Willing to travel to exotic and tropic environments.
  • Must always wear a shirt, no matter how hot it gets (bare chested is for douche bags).

3. Dr. Doom

He spreads his legs out as a sign of dominance.

Why it would be great…

Dr. Doom is best known as the antagonist of the Fantastic Four. He hates Reed Richards, and loves Sue Storm. He probably hates Ben Grimm, and Johnny Storm too but he’d probably fake affection if it would impress Sue. However, did you know he also rules his own country? Yup, Latveria. And would you believe it’s fucking awesome there? Yup. For a villain, he’s carved out a really well run, efficient, and reason-run society. It’s very technologically advanced and safe. Living there is a pretty sweet gig, although the robot police are a little less reasonable than the more meat and flesh variety. Doom understands how to keep his people happy, so why not his employees? There’s a good chance that by working with him, you get a home in Latveria too. It’s like living in North Korea, with a slightly less insane ruler and a less horrible existence.

Why it might suck…

You're not sure why, but any mention of squirrels in Latveria is met with harsh punishment.

For all his boons to his people, Doom is still a guy named Doom. His aspirations are still for world domination, and he’s pretty good at getting there. For someone who gets so close so often, if someone told him he could get there if he only boiled his people alive, he might consider it. He’s also a bit of a dick. I mean this guy is smart, super smart. He’s only barely beaten out by Richards himself, but at least Doom knows how to give his women some attention while splitting atoms. Working with him, even if you think you did a perfect job, to Doom you probably did it so haphazardly you come across as a toddler who somehow got the square block through the circle hole with a whole lot of jamming and plastic hammer. He’s not going to let it slide either, he’ll let you have it, but it’ll be done with such a rich vocabulary that you’ll think he’s just practicing for Hamlet with you.

Necessary Job Skills

  • Latverian citizenship and/or a robot.
  • Able to accept criticism, no matter how harsh or verbose.
  • Acceptance that Doom is so much better than you.
  • Hatred of squirrels and their stupid tails.
  • Never describe anything as “fantastic.”

2. Hank Scorpio

He didn't even give him his coat. I'm at a loss.

Why it would be great…

We’re back to the Simpsons again, and this time with a villain that is more successful than Burns and not anywhere near as hated. In fact, he’s a really nice guy! Homer goes to work for him (seriously, how does he do it) at one point and gets set up in a sweet new home in a wonderful, bum-free, neighborhood. Hank is incredibly friendly and energetic, and he does this trick with a jacket that…well you just gotta see it! Blew my mind. Underneath the friendly exterior, Hank is actually an international super villain, similar to a Bond villain. The difference is that he actually wins! He seizes the whole east coast and uses some of his spoils to buy Homer a football team (although it was the Broncos).

Why it might suck…

Just look at how happy he is!

He’s still a satire of a Bond villain. Which means that goon work comes with almost certain death. While he does win in the end, you still get to see Hank being invaded by the jerk ass military. Now, from what was seen, and knowing the outcome, being on Hank’s side would improve your chances a bit, but I’m certain more than a few people died during the raid. I can’t imagine what happened to all those families in that idyllic little neighborhood either. But hey, maybe he’ll target the West coast soon and he’ll need some applicants.

Necessary Job Skills

  • Willing to relocate to a wonderful little slice of heaven.
  • Discretion.
  • No strong political ties.
  • Type at varying speeds, depending on how hard your boss wants you to work.
  • A coat.

1. Mayor Richard Wilkins, III

Strong teeth are necessary when you eat 1,000 live demon spiders.

Why it would be great…

This is the absolute nicest guy you’ll ever meet. Seeing him be the villain makes you want to see him win. He’s just so upbeat and positive, how can his goals be evil? Okay, so he wants to rule the world by turning into a snake demon, and he enlists the help of demons and vampires, but omelets, eggs, you know the drill. It’s politics! Wilkins is so nice that he was even able to gain the favor of hardcore bad girl Faith, a girl who wears more form-fitting leather than cows. He convinced her that life isn’t all bad, and that there are those who care about her – and he supported her more sociopathic tendencies.  He also gave a job to the first black man ever seen in Sunnydale, Mr. Trick. The man is progressive. He can be a bit of a prude, but he’s just so swell that you don’t mind trading in your Girls of Sunnydale High poster for a Garfield word of the day one.

Why it might suck…

Mondays, amirite?

For one, he employs vampires. Like it or not, with vampires around you’re never going to at the top of the food chain, literally. Sure he keeps a short leash on them, but he can’t be everywhere at once. Plus, you live in a town where disappearances and deaths via puncture wounds to the neck are so common they only carry at $50 fine if you’re implicated. Second, the guy is immortal, or pretty close to it. He’s only the third Richard Wilkins because he has to keep up appearances. The guy founded the town of Sunnydale, and in order to keep up appearances, he poses as the son of the last Richard Wilkins and takes the position of Mayor again. So what does this mean for you? It means you can never be Mayor. No matter how hard you try, you’re never going to be the mayor while he’s around. But hey, maybe you’ll get lucky and he’ll get exploded at the high school. Stranger things have happened, right?

Necessary Job Skills

  • Experience in political environments
  • Good hygiene.
  • Willing to work at night.
  • Knowledge of the occult.
  • Love Family Circus (hate Marmaduke).
  • Punctuality.
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