50 Cruellest Movie Bosses

It’s hell being under them

Randolph and Mortimer Duke (Trading Places)

The Movie Boss: Old and wealthy, the Duke brothers, Randolph (Ralph Bellamy) and Mortimer (Don Ameche) are now so distanced from the real world that they see human beings as pawns for their own games.

Which is why they decide to play out a real life 'nature vs nurture' test by hiring a homeless man (Eddie Murphy) and turning him into a banker.

Cruellest Moment: The Dukes attempt to get rid of their new creation once and for all at the film’s climax.

Luckily, things don’t entirely go their way.

Peter Weyland (Prometheus)

The Movie Boss: CEO of his own Weyland Corporation, Peter Weyland (Guy Pearce) is obsessed with charting space and searching for life among the stars.

Cruellest Moment: Pretty much everything that happens in Prometheus is because of Weyland. He sends a crew of scientists to a deadly distant world where they face certain death.

And all because he wants aliens to prevent his death. Selfish old git.

Vizzini (The Princess Bride)

The Movie Boss: An outlaw, Vizzini employs the giant Fezzik and Inigo Montoya, a Spaniard, as his assistants.

With their help, he is able carry out the evil plans he devises – which doesn’t stop him berating them verbally.

Cruellest Moment:
“Am I going MAD, or did the word ‘think’ escape your lips?” rages Vizzini at one point. “You were not hired for your brains, you hippopotamic land mass.”

Hilly Holbrook (The Help)

The Movie Boss: A privileged, entitled snoot, Hilly (Bryce Dallas Howard) is the worst kind of boss – she treats her employees like disease-ridden animals.

She even insists that her housemaids use a separate bathroom to her.

All the scarier because The Help is based in fact.

Cruellest Moment: Hilly’s maid Minny uses her bathroom during a potentially deadly thunderstorm rather than go outside.

Hilly fires her for it.

Frank Shirley (Christmas Vacation)

The Movie Boss: Mean and unsympathetic, Frank Shirley spares no thought for his employees whatsoever, merely viewing them as drones that help to fill his pockets with cash.

Cruellest Moment: Shirley’s Christmas bonus finally arrives… and turns out to be a subscription to the Jelly of the Month club…

Mark Zuckerberg (The Social Network)

The Movie Boss: A student of Harvard University, Zuckerberg (Jesse Eisenberg) makes history when he establishes website Facemash, which will evolve into Facebook.

Cruellest Moment: Turning on his colleagues/friends in a fight over who owns Facebook.

Or is it they who turn on him..?

We should probably make it clear that we're talking about the movie Zuckerberg here. We're sure the real one is a lovely boss.

Tex Richman (The Muppets)

The Movie Boss: An evil, power-hungry goon, Tex Richman (Chris Cooper) wants to buy the Muppet Studios and demolish them in order to drill for oil.

As you do.

Cruellest Moment: In a moment of total desperation, Richman attempts to derail the Muppets’ live show and stop them making the money they need to restore the Muppet Studios.

Naturally, he fails.

Capt. Dudley Liam Smith (LA Confidential)

The Movie Boss: Callous and unforgiving, Captain Dudley Liam Smith (James Cromwell) works in 1930s Los Angeles.

Cruellest Moment: Smith takes the ‘cruel to be kind’ route when he confronts Ed (Guy Pearce) over his by-the-book approach to policing.

“For the love of God, don’t be a detective,” he advises.

Jack Field (The Good Girl)

The Movie Boss: The store manager at Retail Rodeo, Jack Field (John Carroll Lynch) looks at his staff with nothing more than total disdain.

Which, of course, grates with bored worker Justine (Jennifer Aniston).

Cruellest Moment: Field shows he has pretty much zero compassion in the wake of the death of employee Holden (Jake Gyllenhaal).

“Holden was a thief and a disturbed young man and what happened was a sad thing,” he says over the store tannoy.

“Perhaps we can learn a lesson from this tragedy like don't steal and don't be disturbed.”

Marshall Murdock (Rambo: First Blood Part 2)

The Movie Boss: Marshal Murdock (Charles Napier), a bureaucrat in charge of an operation to root out POWs in Vietnam.

Cruellest Moment: Rambo (Sylvester Stallone) requests extraction from Vietnam when he saves a group of POWs from pirates.

Murdock denies Rambo’s request for fear of the repercussions should the public find out about the operation. Coward.

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