And awaaaaaaay we go...
Special Mention: Blake from Glengarry Glen Ross
Technically, Blake (played by Alec Baldwin in the film version) isn't the boss of the sales team in Glengarry Glen Ross, but he is the guy who is sent by the bosses, in order to so-called motivate the salesmen. And by motivate, we of course, mean scare the fucking shit out of them. But alas, even though he is as big a prick as any old boss, he is not the boss, so Blake only gets a special mention here. The fucking fuck!
Special Mention: Tony Soprano & Michael Corleone
Ya know what? You are working for a mob boss. It should not come as any kind of surprise when they turn out to be bosses from freakin' Hell. They are mob bosses! Bosses in the mob! Yeah, they might be a little on the hellish side to work for. Granted, the benefits are great, but the retirement package...not so much. Aaaaaand, since these are obvious heinous bosses, they go on the special mention board instead of the list proper. This was also a not-so-clever way of getting more bad bosses on the list. Now let's move onto the list itself.
10. Michael Scott/David Brent/Bill Lumbergh
Basicaly these are all the same guy. True, two of them kind of are versions of each other (duh!), but all three are terrible bosses. Whether it be Steve Carrell from The Office or Ricky Gervais from the original UK version or even Gary Cole as the office manager in Office Space, you get nothing but a gaggle of middle management douchebags, all believing they have more power than they actually do. Someday they will find themselves in some sort of cubicle'd middle management Hell, just like they put there hapless employees through.
9. Mr. Dithers
Poor hapless Dagwood Bumstead. Poor mailman-knocking-over Dagwood Bumstead. He is always running late, and then has to put up with Mr. Dithers when he does finally rush and bumble into work.I mean, the guy has repeatedly physically abused Dagwood - with no repercussions. Really? Shouldn't Dagwood go to the police or the better business bureau, or some such place? But then again, Dithers can be a softee sometimes...sometimes! Overall, the man is an abusive lout, and a definite boss from Hell!!
8. Dr. Evil
Yeah, in the end he was a big ole softee, but as a boss, he was kind of a big old douche. Trap doors to send undesirable employees to their fiery deaths. Sharks with frickin' laser beams attached to their frickin' heads! Yeah, not the best boss material. Hell, look what he did to his own son, when he was working for him. Yeah sure, in the end, Dr. Evil sides with Austin, and helps to save the world, but before that...sharks with frickin' laser beams attached to their frickin' heads!
7. Ari Gold
A total fuckin' prick, this one. A racist, sexist, homophobic, loud-mouthed total fuckin' prick! Now this is a field I would not want to be part of, being one of the most cut throat businesses out there, and therefore, perhaps his employees know what they are getting into. But still, have I mentioned what a total fuckin' prick this guy is? I have? Good. Granted, Jeremy Piven plays his Entourage character to the very tip top of perfection, which is why we hate him so. But a love/hate thing, right? Hey, I don't have to work for the prick.
6. J. Jonah Jameson
Over at DC's Daily Planet, Clark and Lois have a tough, but quite fair, and often a big softee, of a boss, but his Marvel counterpart, J. Jonah Jameson of the Daily Bugle, is not so fair or even a softee. Bellowing out orders to everyone around him, as if he were a rabid dog, JJJ is truly the comic's biggest and baddest boss from H..E..double hockey sticks. Poor Pater Parker. He comes in with then best photogs, and gets nothing but aggression from his cigar chompin' boss. And really, what is with all the Spidey hate?
5. C. Montgomery Burns
Sure, Mr. Smithers quite enjoys the abuse spewed upon him by his boss, but he's a masochist, so what does he know. As for Mr. Burns' other Springfield employees, it's not such a pleasant place to work. Hell, it is a nuclear power plant to begin with, and then throw in one of the worst bosses in television history, and ya got one Hell of a bad time at work. Perhaps Homer would have been happier if he had gone the Smithers route, and became a love-starved masochist. Then maybe Mr. Burns would not have seemed so bad.
4. Miranda Priestly
I know, calling Miranda Priestly, as played by Meryl Streep in The Devil Wears Prada, a bitch, might be construed as sexist by some over sensitive mamby-pamby.types, but bitch is the word I'm sticking with? Not so thinly based on real life boss from Hell, Anna Wintour, Vogue Editor-in-Chief, Miranda Priestly is truly a bitch from Hell, as well as a boss from Hell. Hell, I hear that one needs to gird their loins, when she enters the office. I wonder if Ms. Wintour was ever actually this bad. Let's hope not.
3. Gordon Gekko
Sure, Miranda Priestly may be a wicked ass boss, but even at her worst, she was never the reason you went to prison, like Gordon Gekko's protege played by Charlie "I'm not winning here" Sheen. Yeah, that's the kind of boss that Gordon Gekko is. Michael Douglas' iconic 1980's movie character is easily one of the worst bosses anyone could ever dream of having. Then again, it was all about greed (which apparently, for lack of a better word, is good) and that can never lead to anything good. And he is a bitch from Hell too.
2. Ebenezer Scrooge
Yeah, yeah, I know. After Scrooge's Christmas Eve visitors got done with him, he was a new man, and a new boss, but it is his pre-Christmas antics that put him in the number two spot her. Yeah, you may have been a good guy in the end, but before that, you were a true boss from Hell. No bonuses, little pay to begin with, no charity, long working hours, greed and deception, and you even were going to let a little crippled boy die. Seriously dude, what the fuck was wrong with you. And don't give us any of that last minute Hail Mary crap. So ya went and bought Tiny Tim and his family a Christmas goose. If it hadn't been for those ghosts, you would have let him die, all because you had no respect for his father as an employee. you piece of shit you. But I digress.
1. Darth Vader
Granted, Vader could have easily gone the way of the aforementioned mob boss special mentions. I mean, come on, you take a job working for Darth Vader, you kind of have it coming. He is Darth Freakin' Vader after all. Sure, in the end, the very end, good ole Anakin pops out and Vader does the right thing, but before that, he is certainly one of those bosses from Hell, we have heard speak of. I guess in all reality, Darth Vader is merely middle management, and one could easily make a case for Vader's boss, Emperor Palpatine, as the ultimate boss from Hell. Palpatine never did the right thing in the end, but then, Vader was doing most of his dirty work, so Vader is still the worst, the most heinous of bosses. I've had some bad bosses in my day (see the introduction) but none of them have ever force choked me when I spoke out of turn. Yup.
That's it gang. See ya 'round the web.