Griffin Mill (The Player)
The Movie Boss: Griffin Mill (Tim Robbins) is a high-up Hollywood studio executive who spends his time hearing pitches from screenwriters.
Cruellest Moment: Mill kills David Kahane (Vincent D’Onofrio), a writer he believes has been sending him death threats.
He then proceeds to cover the whole thing up.
Bob (The Assassin)
The Movie Boss: The rather innocuous-sounding Bob (Gabriel Byrne) works for a secret government department that turns no-hopers into trained assassins.
The only catch? There’s no way out. You’re officially dead, and can be killed at any time if you show signs of insubordination.
Cruellest Moment: Bob falsely promises new assassin Maggie (Bridget Fonda) her freedom after one last job.
But that job goes wrong, so Bob sends cleaner Victor (Harvey Keitel) in to get rid of Maggie.
Paula (The 40-Year-Old Virgin)
The Movie Boss: Store manager at electronics outlet SmartTech.
Paula (Jane Lynch) enjoys cutting her employees down to size with a well-placed insult.
Then she smirks and stalks off.
Cruellest Moment: “Andy. Have you ever heard of the term... ‘Fuck Buddy?’” Paula propositions virgin Andy (Steve Carell).
“I'm very discreet... but I will haunt your dreams.”
Margaret Tate (The Proposal)
The Movie Boss: As callous as they come, Tate (Sandra Bullock) is an executive editor in chief who has trampled her way to the top of the pile, leaving a trail of broken people in her wake.
Cruellest Moment: Blackmailing her assistant (Ryan Reynolds) into marrying her so that she’s not deported.
Sure, it all works out great in the end, but that’s a pretty horrendous thing to do, no?
Franklin Hart Jr (9 To 5)
The Movie Boss: According to those in his employ, Franklin Hart Jr (Dabney Coleman) is a “sexist, egotistical, lying, hypocritical bigot”.
Which is pretty much the hard truth.
Promoting only men, he spreads vicious rumours about his female employees and takes credit for their hard work.
Cruellest Moment: Take your pick. He yells at Judy (Jane Fonda) on her first day after her equipment goes awry.
He fires Maria when he overhears her talking about money.
And he passes Violet’s (Lily Tomlin) efficiency proposals off as his own, then refuses to promote her…
Daniel Cleaver (Bridget Joness Diary)
The Movie Boss: Suave to the extreme, but also a total dog, Daniel Cleaver (Hugh Grant) is the floppy-haired boss of a London publishing house.
He spends most of his time sending flirty emails to impressionable singleton Bridget Jones (Renée Zellweger).
Cruellest Moment: Cleaver’s cheating ways are exposed when Bridget discovers him in a compromising position with colleague Lara (Lisa Barbuscia).
Happily, this discovery leads to Bridget laying the smackdown on Cleaver with the immortal line: “I’d rather have a job wiping Saddam Hussein’s arse.”
Ebenezer Scrooge (A Christmas Carol)
The Movie Boss: Alastair Sim plays perhaps Dickens’ most famous character, the dastardly Christmas-hater who’s famous for his greed and lack of empathy.
Cruellest Moment: Scrooge refuses to help two men who are looking to raise funds to help the poor.
Instead of dipping into his own pocket, he comments that he already pays taxes for that sort of thing…
Diana Christensen (Network)
The Movie Boss: Heading up the programming of television network UBS, Diana isn’t above making a clandestine deal – as shown when she makes a deal with some terrorists for a new docudrama series.
Cruellest Moment: “You are television incarnate, Diana,” accuses colleague Max after Diana’s devotion to her job results in the dissolution of their romance.
“Indifferent to suffering, insensitive to joy. All of life is reduced to the common rubble of banality.”
Henry F Potter (Its A Wonderful Life)
The Movie Boss: An emotionless slumlord, Potter (Lionel Barrymore) thinks only about money and the survival of the Building and Loan, in which he is a major shareholder.
Cruellest Moment: Potter turns down George’s (James Stewart) appeal for help via a loan.
Not only that, but he openly mocks him and puts out a warrant for his arrest.
Talk about pushing a man to the edge.
Patrick Bateman (American Psycho)
The Movie Boss: A suave and sophisticated exterior belies the dark heart of Wall Street wolf Patrick Bateman (Christian Bale).
He’s competitive to the extreme and has some rather disturbing fantasies.
Cruellest Moment: Bateman invites his secretary Jean (Chloë Sevigny) to dinner, then considers murdering her in his apartment by holding a nailgun to her head…