Michael Corleone (The Godfather Part II)
The Movie Boss: The head of a booming crime syndicate, Michael (Al Pacino) has made it his mission to expand the family business across Hollywood, Las Vegas and Cuba during the 1950s.
Cruellest Moment: Taking his position just a little too seriously, Michael kills Fredo (John Cazale), his own brother…
Thought, to be fair, he did have it coming. "I knew it was you, Fredo."
Les Grossman (Tropic Thunder)
The Movie Boss: Every studio’s worst nightmare: Les Grossman (Tom Cruise) is a tantrum-throwing, expletive-spewing executive who’s producing the movie Tropic Thunder.
In short: he’s mental.
Cruellest Moment: Grossman threatens to cancel the whole movie if things aren’t put back on track – no matter what. Talk about harsh.
Meredith Johnson (Disclosure)
The Movie Boss: When DigiCom, a Seattle software company merges with a publishing company, Meredith Johnson (Demi Moore) snags the promotion that Tom Sanders (Michael Douglas) was expecting to land.
Cruellest Moment: When Tom rebuffs Meredith’s sexual advances, she files a sexual harassment report against him.
Which is only just the beginning…
Mr Sheldrake (The Apartment)
The Movie Boss: A smarmy bigot who’s a manager at a national insurance corporation.
Cruellest Moment: Sheldrake’s affair with a young girl who works, uh, under him at the company comes to a tragic end when she attempts to commit suicide because of he way he's treated her.
Richard Dick Jones (RoboCop)
The Movie Boss: The Senior President of Omni Consumer Products, Jones is a man with a plan – he wants to entirely decimate Old Detroit and build the utopian Delta City in its place.
Cruellest Moment: When RoboCop creator Bob Morton (Miguel Ferrer) is promoted, Jones gets revenge by hiring Clarence Boddicker (Kurtwood Smith) to kill him.
Bill Lumbergh (Office Space)
The Movie Boss: Mug-clutching vice president of Initech Division and boss to Peter (Roy Livingston).
Cruellest Moment: This: “I'm gonna need you to go ahead come in tomorrow. So if you could be here around 9 that would be great, okay?
“Oh, and I almost forgot, I'm also going to need you to go ahead and come in on Sunday too, okay?”
Also, exiling Milton Waddams to the basement. And stealing his stapler.
Amon Gth (Schindlers List)
The Movie Boss: A senior SS officer, Amon Göth (Ralph Fiennes) is a psychopathic sadist who’s tasked with running the Paszów concentration camp.
He often murders prisoners for entertainment. He's very, very, very evil.
Cruellest Moment: Göth decides to execute a hinge-maker in the camp who he deems unfit to live. Except his gun won’t seem to work…
Katharine Parker (Working Girl)
The Movie Boss: As ruthless as any Wall Street investment banker you’ve ever met, Katharine Parker (Sigourney Weaver) is beautiful, successful and ambitious.
She’s also a massive bitch.
Cruellest Moment : Aside from sending her secretary Tess McGill (Melanie Griffith) on numerous, ridiculous wild goose chases, Katharine also reads Tess’ diary and accuses her of stealing her idea.
Dr. Evil (Austin Powers)
The Movie Boss: Owner of his own night club (Electric Psychedelic Pussycat Swingers Club), Dr Evil (Mike Myers) has hugely evil plans for the world, which he routinely attempts to conquer.
Unfortunately, most of his plans are outdated in the modern world, revealing his origins as a 1960s mastermind.
Cruellest Moment: Much of Dr Evil’s bile is directed toward teenage son Scott (Seth Green).
He frequently ignores and humiliates him, most notably in The Spy Who Shagged Me ’s ‘zip it’ sequence.
Gordon Gekko (Wall Street)
The Movie Boss: A corporate raider and renowned in Wall Street circles as a ruthless shark, Gekko (Michael Douglas) is all about big bucks and easy sells.
Cruellest Moment: Turning father on son in a clever power play that shows just how far his protégé Bud (Charlie Sheen) will go to succeed.