The Bosses of Them All: Why Employers Are So Horrible in Movies and TV

With Melissa McCarthy’s The Boss giving us another horrible employer on the big screen, we wonder where all the good bosses are.
By  · Published on April 4th, 2016

This week, another movie about a bad boss is coming to theaters. Why? Where are all the movies representing the great employers out there? If you do a search for listicles on great bosses in film, you’re not going to find much. If anything, they tend to share an article with a more prominent list of the worst. That’s just the perpetuated stereotype we have to deal with. We are taught, through movies and TV shows, that all bosses are horrible.

Actually, it’s a bit of a catch-22 for Hollywood. It’s not necessarily that they’ve set out to make viewers hate bosses. Bosses were bad long before movies and TV. The world was built on the exploitation of workers. And slaves. It’s more that Hollywood wants audiences to identify with that common idea of the disliked boss. Then they go for the extreme in showing something slightly relatable yet even worse than anything you could possibly know.

It’s part of the American Dream to hate our boss. If we all loved our bosses, we wouldn’t strive for upward mobility. We would be fine stuck in the same position doing the same thing for the rest of our lives. Any movie or TV show where the main character advances through luck or hard work, they need a bad boss to show what they’re escaping from. Well, unless the way up is to marry the boss, yet even then sometimes, like in The Apartment, the boss is still a jerk.

When I think of the significance of bad bosses, the sitcom Roseanne comes to mind. This was a show that, after years of TV recognizing wealthy or upper middle class families, honored the working class. Roseanne Barr’s eponymous character begins the series working in a plastics factory, and by the end of the first season not only quits because of an awful new foreman (the previous one was only obligatorily disliked) but leads a walkout of her fellow workers.

After a few seasons of Roseanne going through various jobs, she and husband Dan (John Goodman) start their own motorcycle repair business. That ultimately fails, but then Roseanne starts another business, a lunch counter. By the end of the series, they also win the lottery (or don’t, given the twist reveal in the last episode), but before that they’ve already risen from being poor working class to at least getting by, and it’s through the freedom of entrepreneurship.

The irony of these small business enterprises that we see in so many movies and TV shows (including The Wonder Years, Baby Boom, Waitress, Entourage, Cheers, Sunshine Cleaning, Jerry Maguire and Parks and Recreation) is that the characters have typically become bosses themselves. Now they should be hated by someone else working for them. Instead, the heroes are meant to supplant the evil boss to be the best boss.

The Boss, which opens this Friday, aims for another kind of revolution in the employer/employee relationship. Melissa McCarthy plays the typical terrible big boss (a character she created back in her early improv troupe days), but after she goes to prison for insider trading, she gets to turn things around and become a beloved boss following her release. Instead of reentering society and having to work for her old employee (Kristen Bell), she takes the initiative and leads a new small business enterprise by taking over a scouting troop and selling brownies. And, I presume, learns what it means to be a good employer in the process.

This isn’t actually a totally fresh idea. Six years ago, one of cinema’s all-time worst bosses, Gordon Gekko (Michael Douglas) got another chance by getting out of prison in Wall Street: Money Never Sleeps. And while it takes him some time, by the movie’s end he’s atoning for his past and becomes a relatively good guy. Similarly, in 2006’s The Devil Wears Prada, the wicked Miranda Priestly  (Meryl Streep) does something nice at the end that makes her redeemed in the audience’s mind. And even on Roseanne, the character’s old boss (played by Martin Mull), whom she disliked, ultimately becomes her business partner and friend.

They all could owe something to Charles Dickens’s “A Christmas Carol,” published 173 years ago. Ebenezer Scrooge is the quintessential bad boss turned good. Why aren’t there more of them in the stories of today? It’s not that it’s less relatable. Seeing a mean manager suddenly turned nice is as much of a fantasy as seeing them punished. One reason is probably that movies with characters like Scrooge, who turn around like Scrooge does, may just seem to be modernized takes on “A Christmas Carol,” like Scrooged.

“A Christmas Carol” is also, like The Boss, a story focused on the employer rather than the employee, so it’s more a boss’s fantasy. That makes it less interesting for the common viewer who identifies with the latter. Not because we necessarily need to experience the schadenfreude of punishment but because we prefer to experience the vicarious joy (mudita for you Buddhists out there) of seeing the mobility of those like us.

While The Boss may give us something slightly rare, its familiarity still has me wishing for something more. There are two movies that come to mind that offer interesting takes on the horrible boss stereotype. One is So I Married an Axe Murderer, in which Alan Arkin plays a softy of a police chief who wants to be the sort of mean boss he’s seen in movies and on TV so keeps trying to yell at his employees more.

The other is The Boss of It All, Lars von Trier’s underrated office comedy (set to be remade by Hollywood) about the owner of a company who needs to be hard on his employees to effectively run the business but also wants to be liked by them (basically the reverse of So I Married an Axe Murderer). So he’s made up a fictional boss that he supposedly reports to and whom supposedly is responsible for all the disagreeable parts of the job.


If you’ve ever had a boss that tries too hard to not be hated (see also The Office), you know those are even worse than any hardass in the long run. Chances are, though, you’ve got an okay boss. Probably not too easy nor too hard. Definitely nothing as bad as some of our ancestors throughout history had to endure. Horrible bosses, except maybe those already at the very top, don’t tend to be that successful in real life these days, either.

Perhaps that will be addressed in The Boss, as it deals with a woman who was at the very top now trying to be a boss again at a lower level in life. Or maybe it won’t need to be that in touch with reality because it’s just a movie. Even if not everyone has a terrible boss or hates their supervisor all the time, that’s what we’re were used to seeing on the screen and that’s what audiences will want to see from the new comedy. They can hold off on liking employers in general for Boss’s Day this October.

Christopher Campbell began writing film criticism and covering film festivals for a zine called Read, back when a zine could actually get you Sundance press credentials. He's now a Senior Editor at FSR and the founding editor of our sister site Nonfics. He also regularly contributes to Fandango and Rotten Tomatoes and is the President of the Critics Choice Association's Documentary Branch.