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50 Cruellest Movie Bosses

John Milton (The Devils Advocate)

The Movie Boss: Named after the author of Paradise Lost, John Milton (Al Pacino) is a law firm big wig who gives a job to young up-and-comer Kevin (Keanu Reeves).

Oh, and he’s also Satan.

Cruellest Moment: “Free will. It's like butterfly wings: once touched, they never get off the ground. No, I only set the stage. You pull your own strings.”

Kevin discovers that John is his father (he raped his mother) and is basically indestructible…

Miranda Priestly (The Devil Wears Prada)

The Movie Boss: “Details of your incompetence do not interest me.”

Inspired by Vogue editor Anna Wintour, Priestly (Meryl Streep) is chilly as a block of ice and just as impenetrable.

She’s the boss of aspiring young journalist Andrea (Anne Hathaway), who knows next to nothing about fashion.

Cruellest Moment: Miranda puts Andrea well and truly in her place during a look at a new collection, publicly humiliating her in front of her staff.

Not to mention the moment where she sends Andrea out to get a copy of an unpublished Harry Potter book...

Skeletor (Masters Of The Universe)

The Movie Boss: Egotistical, power-hungry and a little bit bonkers.

Oh, and he has a face like molten wax.

Skeletor’s the biggest threat to Eternia, which he wants to seize for himself.

Cruellest Moment: When his motley crew of mutants fail to acquire the Cosmic Key for him, Skeletor shows how he feels about failure by killing the reptilian Saurod.

Make a mistake, you die. Before you've even had a chance to fill out a HR form.

Mr Burns (The Simpsons Movie)

The Movie Boss: As wicked on the inside as he looks on the outside, Mr Burns has a piece of coal where his heart should be.

He owns the Springfield Nuclear Power Plant and is employer to, among others, loveable oaf Homer Simpson.

Cruellest Moment: Mr Burns confirms his utter lack of compassion when he refuses to help Springfield overcome its power outage.

When Apu attempts to reason with the mogul, he releases the hounds…

Malcolm Tucker (In The Loop)

The Movie Boss: Equipped with a mouth like a viper and a sting in his tail, Tucker’s the Director of communications for the Government, and will stop at nothing to enforce his strict rules.

Cruellest Moment: Tucker convinces a newspaper editor to spike a story by threatening to expose his cheating ways.

“Yeah, maybe it’s better to spike it, yeah. OK. Fuckety-bye…”

Darth Vader (Star Wars)

The Movie Boss: Ashthmatic Sith Lord. Built the Death Star (with a little help, we assume). Doesn't like Jedis very much.

Cruellest Moment:
So many to choose from (revealing his true identity as Luke Skywalker’s father is one heck of a mindfuck).

In terms of cruelty to those in his employ, though, Vader loves using the Force Choke – most notably on poor Moff Jerjerrod.

Dr. Julia Harris, D.D.S. (Horrible Bosses)

The Movie Boss: Think you know sexual abuse? You haven’t seen anything until you’ve seen Jennifer Aniston’s insanely promiscuous dentist.

She makes life a living hell for assistant Dale (Charlie Day), whom she flirts with unashamedly.

Cruellest Moment: Julia drugs Dale and takes photos of him in compromising positions – then threatens to tell his wife they slept together, unless he actually sleeps with her…

Blofeld (You Only Live Twice)

The Movie Boss: The head of evil organisation SPECTRE, he’s a megalomaniac who’s planning global nuclear war. Just because he can.

Cruellest Moment: When Brandt, a SPECTRE assassin, fails to kill Bond, Blofeld seems to let her off the hook.

Then he drops her into a pool full of hungry Piranha…

Cruella De Vil (101 Dalmatians)

The Movie Boss: Lover of all things fur, the aptly-named Ms. De Vil (Glenn Close) is boss to wallflower fashion designer Anita Campbell-Green (Joely Richardson).

She smokes like a chimney and looks sort of like a female version of Skeletor.

Cruellest Moment: Kidnapping Anita’s newborn puppies. What would somebody so sinister want with cute little pups? Well, it’s all about the fur…

Buddy Ackerman (Swimming With Sharks)

The Movie Boss: A movie mogul who hires a new assistant in the form of writer Guy (Frank Whaley), then proceeds to cut him down to size.

Cruellest Moment: “You are nothing! If you were in my toilet, I wouldn't bother flushing it. My bathmat means more to me than you!”

And that’s just one example of Buddy’s constant torrent of verbal abuse…