Horrible Bosses: The 10 Worst On-Screen Bosses

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When people finish work, all they want to do is relax and the last thing they want to do is think about that very thing. However, there are so many movies that feature a boss-type character that we can all relate to and have encountered in our lives at least once.

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Whether it’s a middle manager whose power has gone to his/her head, extremely wealthy Wall Street traders playing mind games, or a sociopathic control freak, movies have depressingly accurately depicted some of the worst people we have all worked with.

10 Fight Club – Richard Chesler

FIGHT CLUB BOSS

Though Richard Chesler would be a lot different if Fight Club was recast today, The Narrator’s boss is one of those managers who is ungrateful for the work that his employees do. However, that isn’t to say he isn’t put through the wringer by them, as The Narrator unfairly projects a lot of his anger on to Chesler.

If any employer found a list of the Fight Club rules left in the copier, they’d undoubtedly have questions, but they wouldn’t be as aggressive as Richard.

9 Tropic Thunder – Les Grossman

Tropic Thunder features a lot of great characters and surprise features from many brilliant actors, but Tom Cruise’s Les Grossman is one of the greatest celebrity cameos of all time.

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Playing the tough studio exec who is producing Tropic Thunder and unsatisfied with the director’s work, the first time we see Grossman, he demands that the sound operator of the movie punch the director in the face. He then goes on to threaten terrorists and dances to Flo Rida as some kind of power play.

8 Horrible Bosses – Bobby Pellitt

HORRIBLE BOSSES - Bobby

Though there are other Horrible Bosses in the movie, Bobby Pellitt is the worst.

Essentially being the titular character of the movie, Pellitt, played by Colin Farrell, is the real boss’ son and when he isn’t threatening to assault his staff, he’s sniffing cocaine in the bathroom, trying to fire people who are overweight and pregnant and trying to get rid of disabled employees. The scariest part is that bosses like this do exist.

7 Office Space – Bill Lumbergh

Clearly being a huge influence on Horrible Bosses and even The Office, Office Space strangely features one of the most realistic depictions of office-based jobs and the bosses that come with them, which is why it’s one of the funniest work-related comedies of all time.

Bill Lumbergh is one of the most passive-aggressive bosses in the way he micromanages his employees, and his slow drawl of an accent makes him one of the most frustrating bosses in movies.

6 The Devil Wears Prada – Miranda Priestly

The Devil Wears Prada features Meryl Streep in one of her more fun roles, as her character has a canon full of savage quotes and a dagger-ish stare. As she could fire somebody for something as little as her coffee not being the perfect temperature or not speaking at the exact volume she wants, employees tiptoe around her when in her presence.

And bosses like this completely do exist, as the character is based on one of the most influential people in the fashion industry, Anna Wintour.

5 Entourage – Ari Gold

Jeremy Piven as Ari Gold on Entourage

As Ari Gold went from an agent to a studio head in the TV show, he was all guns blazing in the movie Entourage, constantly on the attack and playing 5D chess with other industry pros.

As his only ambition is to get Vincent Chase the best movie roles possible, he neglects his family, is intolerably mean to his wife, and more than anything else, treats anybody who works under him as completely replaceable.

4 Trading Places – Randolph And Mortimer Duke

Coleman & The Dukes Trading Places

Being one of the classic movies that Hollywood will inevitably remake, Trading Places sees two elite stock brokers fire an intellectual, well-educated employee, and replace him with a homeless, uneducated drug addict.

They do it for their own sick games and in the end, the Dukes try to ruin both of their lives, revealing themselves to be the most racist movie bosses at the same time.

3 In The Loop – Malcolm Tucker

Peter Capaldi as Malcolm Tucker in The Thick of It In The Loop

Peter Capaldi first starred as Malcolm Tucker in the British political comedy TV show The Thick Of It for four seasons, but in 2009, the show was adapted into the movie In The Loop.

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Malcolm Tucker is a spin doctor who runs between 10 Downing Street and MPs, essentially acting as the backbone of the British government and trying to keep the press at bay. The role obviously comes with a lot of stress, but not only does he fire somebody at every chance he gets, but he straight up starts a war in In The Loop.

2 The Devil’s Advocate – John Milton

Al Pacino in The Devils Advocate)

As it’s no secret that John Milton, a lawyer who takes an apprentice under his wing, is the devil in disguise, there was no better actor to play him than Al Pacino.

The actor’s performance is one of the best on-screen depictions of the devil, and he is truly evil. The Devil’s Advocate features literally the evilest boss an employee can possibly have, but there are still real-life bosses who are somehow worse.

1 The Social Network – Mark Zuckerberg

There’s only one boss who could possibly be worse than the devil himself and that’s the “protagonist” of The Social Network. Having taken the idea of Facebook for himself, the character of Mark Zuckerberg is borderline sociopathic in the movie, as he keeps certain secrets from certain people and sadistically pits employees against each other.

Though the movie only covers the inception of Facebook and not the corrupt actions it has been accused of lately, it still remains the best Aaron Sorkin movie.

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