Crave More Horrible Bosses? 4 More Bosses And 2 Devils Worth Watching

Workplace movies aren’t a regular occurrence, which is odd since most people who go to the movies have a job of some kind. You would think Hollywood would want to ride that subject into the ground with multiple comedies and dramas set in or around an office. But people go to the movies as a means of escape, so it’s understandable why they’d decide to pass on seeing something about a downsizing company (The Company Men) or a documentary on the stock market crash from a few years ago (Inside Job – arguably the scariest movie released in 2010). But a comedy like Horrible Bosses changes all that. Mostly, because everyone has a story about a bad job experience. So they can relate to seeing someone belittled by an obnoxious employer. While the movie offers three loathsome bosses, here are six more that are worth revisiting.

There are no set requirements on what makes for a bad boss. You have your yellers and the ones who play mind games. Some let their actions speak for them, while others are hands-off, doing as little as possible. You have your confrontational types, passive-aggressive types, and those who crave opulence. All of those characteristics could describe Buddy Ackerman. Everyone points to The Usual Suspects as the film that catapulted Kevin Spacey’s career. While that is true, his performance in Swimming with Sharks, which arrived in theaters four months prior to Suspects, may be the best character he’s ever played. Here he plays a movie producer who belittles his meek assistant, Guy (Frank Whaley, aka the “What?” guy from Pulp Fiction), to no end. Buddy is truly the boss from hell. He makes him do meaningless errands at all hours of the day, but it is his constant insults and outbursts that make his character one of the best bad bosses. The relationship gets worse and worse, until Guy snaps after being fired over the phone. He kidnaps and holds Buddy hostage. The last half hour attempts to explain why Buddy treats Guy so badly, and it all leads to a surprising climax. Swimming with Sharks is THE movie for anyone who has ever thought about getting back at his boss. Guy’s payback leans heavily on the side of being masochistic, but is the type of self-actualized wish-fulfillment that people can embrace (tongue placed firmly in cheek).

Meryl Streep is regarded as one of the best actresses of all time, and for good reason. She can take a role and make it truly memorable. One of those roles was that of Miranda Priestly in The Devil Wears Prada. She’s the devil in the title, and like Buddy Ackerman she also directs most of her frustrations toward her assistant, Andy Sachs (Anne Hathaway). Miranda is great at what she does (editor of a popular fashion magazine), but it is the fear that she instills in her employees why she’s deserving of being labeled a horrible boss. When we first see her arriving to the office, Nigel (Stanley Tucci), the magazine’s art director, warns the rest of the staff to gird their loins. Right there we already suspect Miranda of being an unpleasant person to work for. Delivering insults to Andy and making her do impossible tasks (like getting the latest Harry Potter novel before anyone else), Streep’s character is essentially Cruella De Vil with a Prada bag instead of one hundred and one Dalmatians.

This next choice is a bit of a stretch when it comes to discussing movies with horrible bosses. When David Mamet’s Pulitzer Prize winning play Glengarry Glen Ross was adapted as a film it included a character that wasn’t in the original play. Alec Baldwin plays Blake, a real estate sales strategist who is brought in to help motivate an office of desperate salesmen who struggle to make sales. In a film that features such acting heavies as Jack Lemmon and Al Pacino, along with Alan Arkin and Ed Harris (as well as Kevin Spacey, who is the feeble office manager), it is Baldwin who is the most memorable. His part is small – just one scene – but his arrogance and bullishness hits the four salesmen directly where it counts: their pocketbooks. The role is so good that writer/director Ben Younger sampled it for his film Boiler Room when Ben Affleck delivers a speech on what it takes for a stock broker to be a millionaire.

Al Pacino has played a number of dubious characters, most famously Michael Corleone (The Godfather) and Tony Montana (Scarface). Both ruled over criminal empires, but when I think of Pacino as a boss I turn to The Devil’s Advocate. As John Milton, the senior partner at the New York law firm of Milton, Chadwick and Waters, he presents himself as a very endearing person at first. He dispenses advice to a young, hotshot defense attorney, Kevin Lomax (Keanu Reeves), helping him in trial before offering him a large salary and living arrangements in a posh Manhattan apartment. Little does Kevin know that he’s made a deal with the devil. Literally. (You just thought Buddy Ackerman was the boss from hell.) It sets up a climax where Kevin comes to the realization that John Milton is indeed Satan. Pacino’s performance is why The Devil’s Advocate is as enjoyable as it is. And you can place it alongside Tony Montana and Lt. Col. Frank Slade (Scent of a Woman) as his most quotable characters. The film is also the reason why you should never draw the ire of your superior at work. He or she just may be the devil.

1987 was a strong year for movies that have remained some of my favorites. The Princess Bride, The Lost Boys, The Monster Squad, and The Untouchables for starters. It was also a good year to be ruthless. Michael Douglas may have advocated that “greed, for lack of a better word, is good” in Wall Street, but Ronny Cox in RoboCop is just as guilty. Douglas’s Gordon Gekko character may be the better performance, but RoboCop offers more replayability. Cox plays Dick Jones – even his name signals blowhard – the senior VP of Omni Consumer Products (OCP), a mega-corporation that runs Detroit’s police force. Dick doesn’t like competition so he goes to extreme lengths to take out an ambitious young executive. He also makes it impossible for RoboCop (Peter Weller) to arrest him (or any senior member of OCP). That’s not playing fair. It may not make him horrible, but it is very sneaky. (Don’t worry – RoboCop gets him in the end. The payoff is glorious.)


The last horrible boss is a lay-up pick. If you’ve ever worked in a cubicle, then you have probably encountered somebody like Bill Lumbergh (Gary Cole) from Office Space. Those bosses that peer into your cubicle making small talk before saddling you with more work. The types that don’t spew cyanide drivel about how incompetent you are, and instead act passive-aggressively on how you should properly do your job. If Wall Street showed us how to cheat our way to obtaining power and wealth, then Office Space showed us how soul-sucking working in a cubicle can be. Lumbergh kills any aspirations employees may have for wanting to climb the corporate ladder.

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