Cataloging Film and TV’s Worst Bosses

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One of the buzziest movie trailers making the rounds this week is for Horrible Bosses — a comedy that finds three working stiffs (Jason Bateman, Jason Sudeikis, and Charlie Day) plotting to kill their evil superiors (Kevin Spacey, Colin Farrell, and Jennifer Aniston). We can’t wait to see it, but it did get us thinking: How will these villains compare to some of film and TV’s worst bosses to date? From the negligent to the scheming to the downright reprehensible, we’ve listed ten of pop culture’s most memorably awful head honchos after the jump.

Ron Swanson, Parks and Recreation

Before you get upset and object, know this: We love Ron Swanson. Love him. But we’re pretty sure that even he would agree that he’s a bad boss. First of all, he’s the director of Pawnee’s Parks and Recreation Department, yet he’s basically a libertarian. More importantly, he prides himself on how little he does. Ron knows that Leslie Knope does all the work in their office, and he appreciates it. His main criteria for hiring an assistant — the wonderfully affectless April — was to ensure that he never had to take any phone calls or meetings. Ron’s greatest wish, which Leslie recently granted on his birthday? To be left alone with his steak.

Franklin Hart Jr., 9 to 5

Not all bad bosses are as lovable as Ron Swanson. Take, for example, Franklin Hart Jr. He is, as Jane Fonda’s Judy Bernly so eloquently puts it, a “sexist, egotistical, lying, hypocritical bigot” who passes over his female employees for promotions while also scheming to get them into bed. In this cult classic dark comedy, Judy and her co-workers, Violet Newstead (Lily Tomlin) and Doralee Rhodes (Dolly Parton) daydream about getting revenge on Hart — and then actually pull it off.

Nigel Wick, The Drew Carey Show

Drew Carey’s British boss — and, in later seasons, his sometime underling — is an odd duck indeed. Never one to censor himself in the workplace, Mr. Wick is sarcastic, sadistic, and full of un-PC comments. Did we mention that he also spent some time in rehab? This was the role that introduced American audiences to Ferguson — and not a moment too soon.

Miranda Priestly, The Devil Wears Prada

Meryl Streep’s Miranda Priestly, famously modeled on Vogue editrix Anna Wintour, is your worst nightmare. If you look at her the wrong way (or, really, dare to look at her at all), it’s off with your proverbial head. To say that Miranda is exacting is like saying Streep is a decent actress — a massive understatement. She’s cruel (who would ever call Anne Hathaway fat?), manipulative, and stuck up. She will call you at all hours of the night demanding unreasonable favors. Ignore that phone call at your peril.

Wilhelmina Slater, Ugly Betty

Basically the TV equivalent of Miranda Priestly, Vanessa Williams’ Wilhelmina Slater is another fashion-magazine megalomaniac. But instead of torturing her assistant, the bitchy Marc St. James (Michael Urie), she takes him into her confidence, eliciting his help in scheme after scheme to depose her rival, MODE editor-in-chief Daniel Meade (Eric Mabius).

Mark Zuckerberg, The Social Network

We have no knowledge about what it’s like to work for the real Mark Zuckerberg, but Jesse Eisenberg’s fictional version is a nightmare. He screws you over financially, throws temper tantrums, makes you work crazy hours, forges dubious friendships with internet-famous douchebags — and after all that, he still feels sorry for himself because some girl dumped him or whatever.

Don Draper, Mad Men

This one is kind of debatable. Yes, he’s brilliant at what he does. And in an office where the other two bosses are Bert Cooper and Roger Sterling, he often appears to be the sole voice of reason. But he also gets drunk in his office, disappears for long stretches of time, and makes a habit of bedding (or, you know, marrying) his secretaries. And need we even remind you of last season’s showstopping episode “The Suitcase,” in which Don makes Peggy stay late at work on her birthday and they fall asleep on each other, and it’s super-awkward because it’s clear Peggy has a better-hidden version of the same crush every other girl has on Don?

Jeff Sheldrake, The Apartment

Think your boss is a nightmare at work? Well, how would you like to be C.C. Baxter (Jack Lemmon), whose superior, Jeff Sheldrake (Fred MacMurray), has approved his promotion — on the condition that C.C. allows him to use his apartment for entertaining women? That’s not even the worst part. It turns out that the woman Sheldrake is conducting an affair with is the elevator operator C.C. has his eye on. Ugh.

Edina Monsoon, Absolutely Fabulous

You wouldn’t know it to look at her, but AbFab‘s Eddie is actually a pretty powerful woman. She’s the head of a PR firm, which explains her odd fashion sense and all-consuming compulsion to keep up with youthful trends. But, evidently, she doesn’t often feel the need to go into the office, relying instead on the airheaded efforts of her equally colorful assistant, Bubble. As for Patsy, did you realize that she was a magazine editor? Jeez, we’re starting to think TV writers have something against women in media…

Bill Lumbergh, Office Space

Before David Brent and Michael Scott (who we’re not including here because we’re kind of sick of talking about The Office, OK?), the archetypal terrible boss was Office Space‘s Bill Lumbergh. Initech’s VP micromanages, condescends, and manipulates. Every other word that comes out of his mouth is a corporate euphemism. In short, he’s the boss who treats you terribly but thinks you love him. New college grads and others entering the job force for the first time, make sure you watch out for this guy.