What We Do in the Shadows: 5 Brain Draining Bosses Who are Worse than Colin Robinson

The talent pool in the office must be pretty shallow wherever it is Colin Robinson (Mark Proksch) works. He gets promoted to boss in episode 5 of What We Do in the Shadows season 2 and doesn’t even know what his company does. Not that it matters to Colin Robinson (you really have to say both names after hearing Nandor’s relentless enunciations). He doesn’t work there for the money. He’s not there for the prestige. But when he gets a taste of the power, he can’t get enough. He is a kid in a candy store, a junkie at a shooting gallery and Homer Simpson at an all-you-can-eat buffet rolled into one.

With power comes abuse and TV series are filled with abusive bosses. Colin may be emotionally draining and his interoffice meetings may be boring enough to put a printer-paper-feeder to sleep, but he’s not the worst boss on TV. Sure, Colin can suck a soul dry with a click of the tongue and snap of a finger, but he leaves them some breathing room. That way they can recover and he can do it again. TV is filled with lovable bosses like Michael Scott of The Office or Ron Swanson of Parks and Recreation. They do their best to keep their workers content. But there are some awful bosses we love because they really lack any concern for people they can replace with a quick ad on craigslist.

Montgomery C. Burns on The Simpsons

Release the hounds, this staff meeting is adjourned. Mr. Burns, voiced by Harry Shearer, runs the Springfield Nuclear Power Plant, is the richest man in Springfield and yet, as he confides to Homer in a snowy crypt, he always yearns for more. He sold the plant to Germans out of desperation and bought it back at a profit. He slashes costs by trashing dental plans, bribing safety inspectors, and personally dumping nuclear waste into the town’s water supply. And those are his good points. He’s also stolen the sun, made loafers from gophers because he couldn’t kill his chauffeurs, and used a recycling plant to pollute the ocean. Burns routinely has his employees beaten, and even hires someone to watch and laugh at the proceedings. He has unethical hiring practices, pushed his workplace advantage when he tried to date Marge when she was an underling and has kept his assistant Smithers in a closet so long, even moths gag. Why, he’s even filled the candy bar vending machines at the plant with apples. 

Tony Soprano on The Sopranos

Even when Tony Soprano (James Gandolfini) is at the office of his legitimate cover business, as a waste management consultant, he bangs his secretary on a desk in his office. So, the things he gets away with as the head of the DiMeo crime family are positively criminal. But make no mistake about it. He is the boss. Maybe not the boss of bosses, but for a glorified crew in Jersey, he acts like Caesar on a bender in Egypt. On The Sopranos, Tony sleeps with his underlings’ goomahs, dips his beak into paydays he’s not entitled, busts balls on intimate subjects, and if you ever want to quit, forget about it. You might as well hang yourself in a garage with a suitcase of lottery winnings at your feet. But that’s not as bad as what happens when you screw up on the job. People have lost fingers, teeth, eyes, nuts and fiancées for doing the wrong thing. And betraying company secrets can get you shot in the face and tossed into the Atlantic.

Gregory House on House MD

Gregory House (Hugh Laurie) is a brilliant doctor, the top in his field. He can hear a sniffle from across a room and know whether someone has an allergy or needs cranial surgery. He also knows which sarcastic crack can send an intern into a fit of hysterics, what rude remark will compel a holier-than-thou hospital guest to run off in search of a rosary to clutch, and how many eye-rolls it takes to make a narcotics cop take a swing at him. House is as addicted to inflicting emotional duress on the team of diagnosticians he oversees as he is to Vicodin. He plays them against each other and against themselves because at Princeton-Plainsboro Teaching Hospital the odds are always in favor of House.

Jack Donaghy on 30 Rock

30 Rock‘s Vice President of East Coast Television and Microwave Oven Programming Jack Donaghy (Alec Baldwin) appears on the surface to have all the makings of a perfect boss. He graduated Princeton, invented the Trivection oven, and his speaking voice was deemed the most suitable in the world to represent the world on intergalactic audio dictionaries. You’ll never catch him after six without a tuxedo because he’s not a farmer. But god forbid you come back from lunch with a little lettuce from a ham sandwich in your hair. Donaghy’s tenure at NBC/General Electric is positively charged with misappropriation of his employees’ time, even using them on criminal trespass with internet identity on the line. He’s fat-shamed on-air talent, drugged temperamental celebrities, laundered bad branding, and pushed vertical integration to the masses. He is a narcissist who actually looks good in the mirror and he’s not afraid to crack it. He routinely takes credit for other people’s work and puts his own success ahead of the company. He touts it all in his book, Jack Attack: The Art of Aggression in Business, which is required reading for bad bosses.

Donald Trump on The Apprentice

Donald Trump (Donald Trump) was a bad boss when he starred on The Apprentice, and continues to be a bad boss on his daily show currently airing on every channel, most of the time. As a real estate mogul he could clear any property, regardless of city statutes or zoning laws. As a reality show boss he could clear a boardroom with his catchphrase “you’re fired,” the epitome of bad boss slogans. As a top boss, he can clear anything but the air. Many of his former employees only wish a firing was the worst part of their exit interview. Some transition into long term assignments at other federal institutions. There may not always be a job at the post office, but there’s plenty of folding duty at the prison laundry.

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