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Bosses from Hell

Sometimes we revere them as idols; other times, we dread them. We’ve all probably had a terrible boss or two in our lives, so it’s no surprise that filmmakers have been inspired by this figure: the stingy jerk, the master of manipulation, the mad tyrant. We’ve collected the most memorable hideous bosses in cinema!

The ruthless Margaret Tate (The Proposal, 2009) is the editor-in-chief of a New York publishing house, who naturally loves to overwork her staff. When she runs into visa issues and is deported from the US over her Canadian heritage, she forces her assistant to marry her.

Katherine Parker (Working Girl, 1988), who at first appears to be a supportive mentor, first encourages Tess to share her ideas under the pretence of helping him, then “shoots” her down and sells them as her own, and of course, casually collects the accolades.

The manipulative and aggressive dentist Dr Julia Harris (Horrible Bosses, 2011, Horrible Bosses 2, 2014), is not afraid to sexually harass her assistant. He even takes compromising photographs of her and threatens to release them to his employee’s fiancée, even telling her that he slept with her unless she agrees to actually have sex with him.

Jordan Belfort (The Wolf of Wall Street, 2013) was a real spree killer on Wall Street with his extreme behaviour. Lacking total self-control, he made illegal millions from insider trading and dug himself into deeper and deeper holes of crime. He offered his employees thousands of dollars over lunch to humiliate themselves in public, and made drug use an integral part of the corporate culture.

Homer Simpson’s tyrannical boss, Mr Burns (The Simpsons, 1990), is unabashedly risking the safety and health of his employees. He overworked and underworked his staff, while taking every opportunity to indulge his sadism, hurting and endangering his subordinates.

Gordon Gekko (Wall Street, 1987, Wall Street: Money Never Sleeps, 2010) is Wall Street’s most successful big gun, ambitious, egotistical, manipulative and ruthless. But he also doesn’t pretend to be a nice guy; he doesn’t apologise for his greed. The character of the cold-blooded shark, by the way, is an icon and role model for brokers to this day.

Our boss is often the devil himself. But what about when we sign a contract with Satan himself? First, John Milton (The Devil’s Advocate, 1997) lures Kevin Lomax, a morally flexible defence lawyer, to a star New York firm, which of course, comes with a hefty salary and a huge Manhattan penthouse.

Fashion magazine’s feared editor-in-chief Miranda Priestly (The Devil Wears Prada, 2006) has terribly high expectations of her staff, whom she constantly berates and manipulates. The protagonist, Andi, has to put up with being deliberately called bad names, insulted in her appearance and given impossible tasks. He also pits his employees against each other and uses his power to force them into unhealthy competition.