The List

The List: 15 Worst TV/Movie Bosses of the Decade

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Sparked by the recent release of Touchstone Pictures’ generic bad boss droner The Proposal, I’ve decided to list some of the last decade’s best examples of the big and small screens’ worst bosses. Whether they’re unappreciative, always cranky, physically or verbally invasive, or just plain dumb, these are the 15 Worst TV/Movie Bosses of the Decade:

Bill (David Carradine), Kill Bill

Ah, Bill. The leader of the Deadly Viper Assassination Squad, Bill is a master manipulator and the coldest bastard since Mr. Freeze. He impregnates the Bride (Uma Thurman), then heads a bullet-plaid massacre at her wedding, putting her in a four-year coma and killing everyone else (including, as we come to learn, a piano-pricklin’ Samuel L. Jackson).

...That’s not very nice.


Dr. Bob Kelso (Ken Jenkins), Scrubs

Kelso, the Chief of Medicine at Sacred Heart Hospital, is a mostly emotionless bully who laughs off his patients’ ailments, forces out those whose insurance plans don’t benefit the hospital’s revenue, terrorizes or ignores the building’s interns and legal consultant, Ted, fires nurses because he doesn’t like them, and even abuses the life-time supply of muffins he won in an M&M-counting contest (I’m talking multiple dozens a day).


Chief Inspector (Bill Nighy), Hot Fuzz

When Nicholas Angel (Simon Pegg), the top cop of London’s Metro Police Service, starts to make the rest of the force “look bad”, this long-faced whiner ships him off to a podunk town called Sandford, where Angel is subsequently called on to track and capture a fugitive goose, babysit law enforcement’s dumbest officer, and outwit Timothy Dalton.


E. Edward Grey (James Spader), Secretary

This one’s a riot. A small-time lawyer running his own firm, Mr. Grey is an impersonal sadist who dismisses his assistants at a rate that would put Naomi Harris to shame. Why? Well, for one, he’s an obsessive-compulsive nitpicker who can’t tolerate so much as an inadvertent sniffle; he also has a subtly unorthodox method of punishment: he binds, spanks, then fires the culprits.


Gob Bluth (Will Arnett), Arrested Development

Gob, a womanizer and Magician’s Alliance—an alliance group for the protection of magicians’ secrets—outcast, acquires Bluth Company Presidency in the series’ second season, and idiotically fires the entire staff because they all laughed at him at a company Christmas party (dozens of suckers were stuck to the back of his suit, which he continuously assured his employees was worth more than any of their attire). What Gob didn’t know at the time was that George Bluth (Jeffrey Tambour), the head of the Bluth family and its company who was in jail for treason, had only dubbed Gob the “President” to keep the media at a comfortable distance from his younger brother Michael (Jason Bateman), who had all the while maintained presidential responsibilities. Unfortunately, the personnel he discarded was unaware of his false authority.


Les Grossman (Tom Cruise), Tropic Thunder

This greedy, overly-hairy, hot-tempered, personal space-invading studio executive screams more than he speaks, screams only in obscenities, and advocates scholarships instead of ownership when it comes to dealing with dead crewmen. “We file an insurance claim…the claim alone would net us more than the movie would lose.” (Not to mention he orders someone to “literally, stand back and [screw] your own face.”)


Michael Scott (Steve Carell), The Office

Contrary to the claim of his favorite coffee mug, Michael Scott could be the world’s worst boss: he’s loud, obnoxious, sometimes cruel (“This is our receptionist, Pam. If you think she’s cute now you should have seen her a couple of years ago!”), always inappropriate (“I love Phyllis…You know what I’m worried about? Getting a boner.”), and too dumb to realize he’s any of those things. And when his workers get up the nerve to tell him what he’s doing wrong, his egotistical infantility denies their complaints entry into his wee brain capacity (he often combats criticisms by mocking he or she who offered them).


Miranda Priestly (Meryl Streep), The Devil Wears Prada

Yes, you already know about this expensively outfitted she-devil (she’s only on every other Worst Bosses list). But it’s imperative to recognize her yet again, if only to save myself from her piercing stare. The Editor-in-Chief of New York’s esteemed Runway magazine, Miranda, like others on the list, simply hates everyone that works for her—or at least believes that they’re all universally incompetent. I suppose that demanding your junior assistant (Anne Hathaway) fetch you two manuscripts of the newest, not-yet-bound Harry Potter novel within a 48-hour time-frame isn’t so bad, but selling out your long-time assistant (Stanley Tucci) to save your own job proves her “ruthless”, “manipulative” nature and frosty manner. She also threatens her employees (particularly Hathaway) with their jobs. Yeah, she’s one of those bosses. Alec Baldwin’s Blake (Glengarry Glen Ross) would be proud.


Paula (Jane Lynch), The 40-Year-Old Virgin

Okay, so SmartTech’s store manager isn’t that bad. After all, she isn’t a fan of firing her employees (even when they are using the home theater system area to videotape their own genitalia) and encourages their enthusiasm with promotions. But she does make Andy (Steve Carell) feel extremely uncomfortable by offering him sex on multiple occasions, and…she doesn’t fire people. (Have you seen the SmartTech staff?!)


Skinner (voice of Ian Holm), Ratatouille

The moment Skinner gained control of Paris’ most coveted 5-star restaurant, Gasteau’s (after Gasteau himself had passed away), he turned from a disgruntled sous-chef to a choleric, domineering, vengeful owner, whose power-driven behavior suggests Napoleon at the time of his imperial reign over the French empire. And when Skinner discovers that his newest subordinate, Alfredo Linguini, is Gasteau’s son and the rightful owner of the restaurant, he gets Linguini drunk and tries to trick him into signing over his right of possession.


Steve Zissou (Bill Murray), The Life Aquatic with Steve Zissou

Steve is a sad oceanographical filmmaker who undermines his interns’ feelings and pleads in favor of alone-time and fuel preservation (he decides to take a “shortcut” through unprotected waters on route to steal another oceanographer’s equipment despite the advice of an intern; his ship gets hijacked by a band of pirates who steal his abandoned son’s vault and machete another intern’s shoulder). As if it couldn’t get worse for his unpaid pupils, he rejects their request to pass them considering all that they went through: “No. I can’t give you full credit, but I’m not gonna flunk you either. You’re all getting ‘incompletes’.”


Ted Jones (Gary Cole), Red (Danny McBride), Saul Silver (James Franco)/Black Doug (Mike Epps), Pineapple Express/The Hangover

These four idiots either deal or traffic drugs, meaning that they’re always in a position of power over others under them or people they’re selling to. So, for the sake of this list, we’ll refer to them as “bosses”. Red, the fat, curly-haired middleman between Ted and Saul is almost as simple-minded as his client Saul is. These two paranoid cretins accidentally become Jones’ primary enemies after one of Saul’s stoned buyers (Seth Rogen) witnesses a hit at Ted’s house—and Ted, played by Office Space‘s classically awful boss Bill Lumbergh (aka Gary Cole) chose to shoot his target in front of his pad’s mammoth wall-covering windows. But even this trio of dumb dealers can’t hold a torch—or a roach—to Black Doug, who mistakenly gives The Hangover‘s groom and three groomsmen Roofies instead of Ecstasy.


Any bosses unfairly not listed? I demand you to share—or else you can pack up your things and clear out your desk by the end of the day.


Also: Every other Monday will feature a new list (the next one will be on July 13), so stay tuned.

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