The Most Infamous Movie Bosses Of All Time

September 10, 2009 by  
Filed under - Home, Features

Anna Wintour somewhat confirmed her reputation as a fearsome boss in The September Issue, which had us all thinking… Who are the scariest bosses we’ve ever had?

Though we’ve had a few tyrants, none are as infamous as the ones we’ve seen on screen.

Infamous bosses come in many breeds, you have the conniving ones, the spineless ones and the ones that will hurl stationery at you.

Join us for a run down of the most infamous movie bosses, and thank your lucky stars that you still get desk ornaments and weekends.

The Devil Wears Prada – Miranda Priestly

We kick off with Wintour’s on-screen characterisation, Miranda Priestly from The Devil Wears Prada.

She expects you to change weather conditions, fetch promo copies of unreleased Harry Potter books, and she wants it all before you hotfoot it across town to get her steak and Starbucks.

Meryl Streep played the Vogue editor flawlessly, with a tongue as sharp and cutting as pinking shears.

Should you quit? No. Having survived the world’s most infamous editrix looks pretty good on your CV.

State of Play – Cameron Lynne

If The Devil Wears Prada has taught us anything, it’s that there are few chieftains more fearsome than an editor.

The 2009 film adaptation of the BBC serial drama State of Play sees reporter Cal McAffey (Russell Crowe) putting his life on the line and plumbing the depths to get the ultimate story.

His editor Cameron Lynne (Helen Mirren) however is not best pleased, a shouty, frightening tyrant of a boss.

Here she is in action:

Should you quit? Hell no. You’ve got a lead on a great story…

State of Play on DVD and Blu-Ray is on general release across the UK from September 21st.

Secretary – E. Edward Grey

Say you’re called in for a “disciplinary” for leaving a turd in the CEO’s drawer or something. What’s the worst you’d expect?

You could be handed a P45, humiliated in front of the office, maybe even receive a retaliation, but any of those would be a welcome punishment compared to E. Edward Grey’s hands-on approach to business.

Clammy Stephen Shainberg-directed flick Secretary tells the story of mild-mannered outcast Lee Holloway (Maggie Gyllenhaal) finding work in an austere lawyers office as E. Edward Grey’s secretary.

Lee’s careless typing at first irritates Grey, creating endless typos in his correspondence, though they are later over-zealously dealt with in the applying of red marks by pen (and otherwise)…

Should you quit? Absolutely not. Boss and you have an agreement. And mutual benefits.

Working Girl – Katherine Parker

Second only to your own, the boss’s yearly holiday is the most anticipated “event” of the year. It means a week or two of turning up late to work, taking two-hour lunches and leaving at four (to miss the rush hour). Oh, the madcap things we get up to in our bosses absence…

When Working Girl boss Katherine Parker breaks her leg in a skiing accident, however, assistant Tess McGill (Melanie Griffith) has to hold the fort.

Finding out Parker isn’t the mentor she made herself out to be, but a quietly conniving idea-stealer with an agenda, McGill takes back what she deserves by pretending to be her as she convalesces. Novel.

Should you quit? No. Stick at the brown-nosing for long enough and you might just bagsy Sigourney Weaver’s job.

Wall Street – Gordon “Greed is Good” Gekko

“Greed is Good.”

Never in recent memory has this maxim had so much resonance, which is probably why a sequel of 1987’s ultimate yuppie flick Wall Street is currently in the works.

It will star Shia LeBeouf, Susan Sarandon, and has Michael Douglas reprising his role as Gordon Gekko, with Oliver Stone returning to direct.

The unscrupulous Gekko subjects the eager Bud (Charlie Sheen) to anything to nab that inside information to trade on and make the big bucks with. He’s ruthless, corrupt and loves a good bark on the phone.

Here’s that legendary “Greed is Good” speech:

…and what Wall Street might look like if Family Guy‘s Stewie Griffin played the “Bud” character, with some ranting and raving:

Should you quit? Yes. If Michael Douglas doesn’t steal your soul then an impending recession might just steal the shirt from your back.

Office Space – Bill Lumbergh

“M’yeah, if you could just go ahead and work on Saturday, that would be great…”

Featuring in Mike Judge’s first live-action feature, based on the “Milton” series of animated shorts, the micro-managing, logo-ed coffee-cup wielding head honcho Bill Lumburgh (Gary Cole) is undoubtedly the most offensive of movie bosses.

Somehow finding his twunt-shaped niche in a company with seven levels of management, Lumburgh relentlessly torments his employees in now trademarked passive-aggressive fashion.

Tired of being made to work weekends and slowly festering in his cubicle with his fellow underlings, Peter Gibbons (Ron Livingston) comes up with a scam to channel money from the company to their bank accounts.

Only a boss this insufferable would push someone to resort to fraud.

Should you quit? Yes. You know things are bad when a stapler is all you have.

Swimming With Sharks – Buddy Ackerman

Surely no other silver-screen boss is worse than this one.

In 1994’s Swimming With Sharks Kevin Spacey plays a film producer boss, the ironically-named Buddy, a man who’s almost Terminator-esque in how efficient and sociopathic he is.

He hires Guy to be his assistant, daily abusing him emotionally and physically and making banal requests such as asking for “Equal” instead of “Sweet-n-Low” sweetener. He’s pure evil but he’s hilarious with it.

There has been much speculation as to who the sadistic movie mogul is based on. While some suspected Buddy was modelled on Scott Rudin, SWS director George Huang used to work as an assistant for Barry Josephson, then the Senior Vice President of Development at Sony Pictures. Not that that means anything.

The video embedding function is boringly disabled, but this nifty DIY slideshow should give you an idea of Buddy’s management techniques:

And here’s a link to its entirety:

You laugh now, but it wouldn’t be funny if he was your boss.

Should you quit? Yes. Before you lose an eye or something.

Leonie Mercedes

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