Horrible On-Screen Bosses We Love to Hate

From the devil who wears Prada to the pencil-pusher with all those TPS reports, be glad you don't work for any of these seriously bad supervisors.

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June 14, 2011 12:00 PM
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Dr. Julia Harris

From: Horrible Bosses
Job Title: Dentist
Sure, Julia (Jennifer Aniston) is one hot doc, but that doesn't mean her dental hygienist Dale (Charlie Day) wants to have sex with her. After he refuses her highly inappropriate advances, she threatens to blackmail him with some seriously saucy pictures she took while he was unconscious. No wonder dentists get a bad rap!
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Bill Lumbergh

From: Office Space
Job Title: Division Vice President, Initech
The only thing worse than having to work for a bad boss is having to work weekends for a bad boss. And that's just what suspender-wearing, micromanaging Bill (Gary Cole) will ask you to do when he swings by your cubicle come Friday at 4:59 p.m. He'll also ask you about those damn TPS reports. Mmm, yeah.
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Miranda Priestly

From: The Devil Wears Prada
Job Title: Editor-in-Chief, Runway magazine
Miranda (Meryl Streep), the demanding woman at the top of the world's premier fashion magazine masthead, lectures assistants on the vast differences between blue and cerulean while forcing them to find manuscript copies of yet-to-be-published Harry Potter books. Her amazing style and icy-cool 'do are only rivaled by her surprisingly soft-spoken insults. (And what makes the boss' impossible-to-please 'tude all the scarier is that it's actually based on one very real editrix.)
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Gordon Gekko

From: Wall Street
Job Title: Corporate Raider
Gordon (Michael Douglas) — with his "greed is good" credo — makes doing bad things look like so much fun. The worst part of working for the cutthroat investor is that you have to sell your soul to do so. And if you don't fall in line, you don't just get fired. Like Gordon's protégé Bud Fox (Charlie Sheen), you get sent to prison.
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Ari Gold

From: Entourage
Job Title: Agent & Senior Partner, Miller/Gold Talent Agency
The neurotic, fast-talking Hollywood agent (Jeremy Piven) may do everything for his favorite client Vince Chase, but for his colleagues and for his assistant, Lloyd — whom Ari often refers to simply as "slave" when he's not cracking crude gay jokes or insulting his race — Ari is a ruthless, equal-opportunity offender.
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Katharine Parker

From: Working Girl
Job Title: Financial Executive, Petty Marsh
One of the gravest sins of a bad boss is when they pretend to be on your side, only to steal your good ideas, which is just what Katharine (Sigourney Weaver) does to her new secretary Tess (Melanie Griffith). When Katharine breaks her leg, Tess seizes an opportunity to get revenge, stealing back her merger deal idea, along with her boss' job — and her man. "Let the River Run," indeed!
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Montgomery Burns

From: The Simpsons
Job Title: Owner, Springfield Nuclear Power Plant
With Homer Simpson as an employee, it's no wonder Mr. Burns has an evil streak. Still, the frail old man — who curls his fingers and mutters, "Excellent…" before doing anything sinister — uses his immense power and wealth to do whatever he wants to the occasionally good people of Springfield … some things so awful they can only really be captured in animation.
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Blake

From: Glengarry Glen Ross
Job Title: Consultant, Mitch & Murray
Blake (Alec Baldwin) sure knows the benefits of negative reinforcement. When the ruthless salesman is brought in to "motivate" the less-than-impressive agents at a real estate firm, he literally dangles a pair of brass balls, imploring the men to obtain a pair of their own. He also coined the douchey ABCs of selling: "Always. Be. Closing."
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Wilhelmina Slater

From: Ugly Betty
Job Title: Creative Director, Mode magazine
Talk about fighting your way to the top: Wilhelmina (Vanessa Williams) is willing to sabotage, seduce, and scheme her way up the corporate ladder. Whether she's forcing an employee to serve as a surrogate after stealing her dead fiancé's sperm (follow that?) or just insulting the regrettable fashion choices of one Betty Suarez (America Ferrera), Willie really is the queen of mean.
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Michael Scott

From: The Office
Job Title: Regional Manager, Dunder Mifflin, Inc.
Michael (Steve Carell) — proud owner of a "World's Best Boss" coffee mug — has no social filter and a desperate desire to be everyone's friend. On rare occasion, he's shown a powerful business acumen, but for the most part, he focuses on awkward office parties and woefully insensitive meetings on such sensitive topics as sexual harassment and diversity. It's a hard, messy job. That's what she said.
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Franklin Hart, Jr.

From: Nine to Five
Job Title: President, Consolidated Companies
It's hard to blame the trio of secretaries for kidnapping and holding Mr. Hart (Dabney Coleman) captive: The sexist manager spends most of his workday trying to take advantage of his female workers. Only when he's out of the picture do women get what's theirs, including job-sharing benefits and flex time. Way to stick it to The Man!
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Michael Corleone

From: The Godfather
Job Title: Head, "The Family Business"
So even if the family business happens to be organized crime, you can still be a good mafia boss, right? Not so for Michael (Al Pacino), who makes people offers they can't refuse and kills his own brother on the job.
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Amanda Woodward

From: Melrose Place
Job Title: Advertising Executive, D&D Advertising
Although she has taken on many roles at the advertising agency, PR big-wig Amanda (Heather Locklear), she managed to backstab her way to the top, even forming her own shop at one point. One successful tactic? Bedding nearly every man in her way. (By the end of the soap, she'd become Mrs. Parezi Burns McBride Blake McBride Burns.)