Every year we celebrate National Boss’s Day because… uh, I guess they don’t have enough going for them already? I don’t know. What I do know is that your boss is probably still better than any of these TV bosses. In real life, you just end up muttering obscenities under your breath while you drive home. But in TV land, these bosses will abuse you, harass you, and in some cases even get you killed. Say what you will about your boss, but at least he probably isn’t giving you a case of PSTD. But these terrible TV bosses are, and that is just one reason why they are the worst TV bosses of them all.
Angela Bower – ‘Who’s the Boss’
Look, on the surface, Angela is a great boss. She even lets her nanny or whatever the hell Tony Danza is live with her and her young son and hornball mother. But she also blurs the lines between professional and personal to the point that Tony is basically her live-in gigolo. Now that might not sound so bad, but flip that shit around for a minute. Imagine if some rich dude hired a single mom to be his housekeeper and crossed those kinds of lines. Jezebel would be writing articles, Twitter would be all, well, atwitter, and OSHA would be sending case workers to the house to handle that shit. The kids would probably end up in foster homes, Mona would get dragged away in chains as a sex deviant, and nobody would be laughing then. It’s called sexual harassment, Angela.
Buck Strickland – ‘King of the Hill’
Without Hank Hill keeping things together, Buck’s propane business would have blown up a long time ago. And how does he thank Hank? By constantly taking advantage of him, trying to bone his niece, dragging him – and his son – along during his epic bouts of degeneracy, and basically tossing Hank to the side whenever anything flashy or with a nice pair of tits comes along. This is the sort of boss who will ruin your life and then fire you when you’re only a couple of years away from retirement just so he can hire a 19 year-old who was in last month’s issue of Hustler.
Michael Scott – ‘The Office’
Michael Scott’s incompetence is the sort of thing that brings an entire office down. This is a dude who will ruin your life and not even understand that he’s doing it. Bad decisions, constant half-assed schemes, poor interpersonal skills… Michael is just a tornado of poop, and everyone in the area will be covered in the stench when he blows through. Sure, he’s friendly – too friendly – but that just makes him all the more maddening. Bosses like Michael are the ones who wind up being chased through their backyard by an employee with a baseball bat who’s finally snapped after years spent trying to desperately cover up for their bosses ineptitude.
Professor Farnsworth – ‘Futurama’
Farnsworth isn’t just a bad boss, he’s damn near a war criminal. His horrible schemes are always on the verge of causing some intergalactic catastrophe or another, and his employees might as well travel with death certificates 90% filled out. And if he doesn’t get you killed, he’ll get you enslaved by giant Amazonian sex addicts or sent back in time to bone your own grandmother. I suppose he’ll get you laid, but those are not circumstances any man should ever have to face. I mean, if you need your boss to get you laid by your own grandmother, you should probably reevaluate some things. In the end, I guess crazy crackpot scientists just don’t make the best bosses.
Don Draper – ‘Mad Men’
Don Draper is the sort of boss who will completely ruin your life. That’s because he will psychologically ruin you. He doesn’t mean to, he just doesn’t know any other way. It’s how he survives. He manipulates and controls and then cuts people loose when they disappoint him. He makes you desperate for his approval by withholding it and then destroys you when you can’t give him exactly what he needs. He’s smarter than you, he’s better than you, and he won’t ever let you forget it. And as the last season or two of Mad Men has proven, you can’t even have blind faith that he’ll lead you to the promised land because the truth about Don Draper: Control Freak is even more disturbing – he’s actually completely out of control, and he will drag you down with him. And he probably won’t even share the good liquor. Unconscionable.
Ari Gold – ‘Entourage’
Ari will scream at you, abuse you, order you to do degrading and impossible things, and then at the end of the day he’ll make it all worthwhile by… insulting you some more. Ari is the boss who will make you eat shit just because he can. He knows you’ll do it because, well, that’s the way Hollywood works. You have to eat your shit before anyone will even give you a nibble of that sweet, sweet pie. But really, the most insidious thing about Ari is that he’ll have a moment here or there where he’ll do something that gains your loyalty, and so you can never really quit him. He’s like Don Draper in that way. You want to please him so badly that you end up just letting him destroy you, and that’s the worst type of boss there is.
Captain Kirk – ‘Star Trek’
This may be somewhat controversial because, come on, it’s Captain Kirk! Adventure! Romance! Space! Unless, of course, you’re a lowly redshirt, in which case it’s more like… Death! More Death! Even more Death! Say what you will about most of the other bosses on this list, or your own obnoxious boss, they probably aren’t casually getting everyone outside their own officer corps killed all the time. And when it’s done, Kirk just picks up some new recruits and moves on to bone green alien ladies while the newbies all get vaporized. There’s a metaphor for Wall Street in there somewhere.
Tony Soprano – ‘The Sopranos’
Yeah, Tony is a badass, but ask yourself this – just who, if anyone, thrived with him as the boss? Sil ended up in a coma, Big Pussy slept with the fishes, Uncle Junior ended up in a shitty old folks home, Bobby and his trains went off the tracks, and for god’s sake, let’s not forget about Christopher. Tony literally murdered him! I could go on and on and on here. Really, Paulie Walnuts probably made out the best in the end, and is he really any better off than when Tony took over in the first place? No. Let’s face it, Tony was a shitty boss.
Mr. Burns – ‘The Simpsons’
Even Hank Scorpio, a literal cartoon villain, was a better boss than Mr. Burns. At least he bought Homer a football team. Sure, it was the Denver Broncos, but the thought counts. What has Burns ever done for anyone? Steal teddy-bears, murder puppies, block out the sun – the list of the ways he ruined his employees’ lives goes on and on. How many times has he brought the Simpson family to catastrophe? And the worst part is, is that he’s not even really an effective businessman. He’s out of touch, his power plant is constantly falling apart, and he was even fleeced by a senile Fidel Castro. He’s constantly fucking up, and yet, through it all, he maintains an iron grip on power. Actually, are we sure this guy is a cartoon? Because that sounds an awful lot like way too many bosses we all know in real life, doesn’t it? Happy Bosses Day.