Bad Movie Bosses

Of course, we all have to deal with a bad boss sometime or another, especially if we’re working a job we don’t like or possibly the only one we could get. Still, when it comes to work, most of us decide to put up with terrible bosses since you really can’t quit a job like you can quit a relationship or what not. After all, people depend on their jobs for so much that they’re willing to put up with 8 hours in hell if they could get a paycheck to pay for their basic needs. And in a job market like this, it’s not easy just to tell your boss where to shove it and throw caution to the winds because getting another job isn’t easy (it’s actually a complete hell, especially if you have student loan bills to worry about). Of course, sometimes the movie world is no exception to this in which a lot of bosses do make their life difficult for their employees. Some of them are incompetent and careless. Some are downright evil and chronic backstabbers. And some just abuse their power as well as cause a lot of destruction. So to salute Labor Day weekend, here is a list of terrible movie bosses you don’t want to work for.

1. Captain Ahab

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From: Moby Dick

Occupation: Captain of the Pequod.

The Problem: Single-minded obsessions which are self-destructive and result in his crew’s endangerment. Also, is practically insane.

Sure we all know that killing whales is a grisly and dangerous profession that requires months away from home in the early 19th century. Of course, people today wouldn’t approve killing whales for lamp oil and other products (besides food if you’re Japanese or a Pacific Northwest Indian) but people’s homes have to be lit some way. Still, Captain Ahab makes the list of bad movie bosses because of how his single minded obsession not only leads to his own self-destruction and insanity but also to the endangerment of his crew and ship. Ahab may be a competent captain who inspires great loyalty in his crew but his obsession with Moby Dick practically consumes him that he cares about little else whether it be his crew’s welfare or focusing on the mission’s bottom line which is to hunt whales. It doesn’t help that his second-in-command Starbuck realizes that his captain has gone insane and shouldn’t be in command.  Even  worse is that Captain Ahab is competent and charismatic enough to get most of his crew to go along with his Moby Dick obsession (not that they had any choice since they’re all stuck on a ship, you know). Still, though Captain Ahab is dragged into the ocean by the white whale in the end, the ship is destroyed and everyone in the crew is dead save the narrator. Let’s just say that such destruction would’ve been avoided if Starbuck’s sense of duty didn’t override his common sense to throw Ahab to the sharks.

2. Willy Wonka

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From: Willy Wonka and the Chocolate Factory and Charlie and the Chocolate Factory

Occupation: Confectionery Industrialist and Entrepreneur

The Problem: Workplace endangerment, caring little for people, and heavily skewed priorities. Also, isn’t quite right in the head.

Let’s face it, despite having a factory to the specifications of any kid’s dream (or nightmares), you don’t want to work for Willy Wonka. Sure he may love his candy and his factory, but we have to understand that Wonka is a nutty recluse and control freak who doesn’t give a damn about other people and he’s very lucky that people in his community don’t have a raging hatred for him. Wonka may have a right to be overly concerned with corporate espionage since the candy business was highly competitive. Yet, firing your entire workforce with perhaps little or no compensation just seems a bit of overkill. And replacing it with a nation of Oompah Loompahs who don’t earn any money for their work kind of seems to add insult to injury. Not only that, but Wonka kind of isolates these people in his factory who may be susceptible to who knows what after he takes a group of kids on a tour. Still, Wonka’s employees may look up to him but he uses them for experiments with candy that wouldn’t be FDA approved and his  factory is basically a dangerous work place filled with all kinds of death traps. And it doesn’t help that Wonka is more preoccupied with aesthetics and his candy than practical safety issues. Not to mention other concerns that the movies haven’t shown. You can read it all here from one of my previous posts: https://historymaniacmegan.wordpress.com/2014/08/21/willy-wonka-and-the-workplace-violations-report/ . And if there’s a movie boss whose workplace violations report can make a good blog post, then Wonka is a very bad boss indeed.

3. Dr. Julia Harris D. D. S.

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From: Horrible Bosses

Occupation: Dentist

The Problem: Sexual harassment, sexual assault, abuse of power, no respect for consent laws or workplace ethics, and blackmail.

Now Horrible Bosses has three people who can be worthy of the World’s Worst Boss mug. Yet, out of these three, Julia Harris seems to stand out for me, especially how she treats her hygienist Dale Arbus. Julia belongs on this list since she’s one of the best movie examples of how sexual harassment in the workplace could make an employee’s life an absolute hell, especially if the harasser is your boss. Sure Julia may be played by Jennifer Aniston, but she’s constantly making sexual advances on Dale who doesn’t like it at all. Of course, Dale is engaged to be married, a fact Julia doesn’t seem to respect and is willing to ruin his relationship unless he sleeps with her, willingly or not. And it doesn’t help that Dale is basically stuck working for her due to being on a sex offender list for public urination near a playground nor the fact that Julia tends to sexually assault her own male patients while unconscious. Basically Julia’s behavior toward Dale makes him feel so powerless and sees her as such a threat to his relationship with his fiancee that he’s willing to commit extralegal activities like murder and blackmail. Being a hygienist for a gorgeous dentist might be a straight man’s fantasy but not if her sex crazed antics have a potential to ruin your life.

4. Fagin

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From: Oliver Twist and its subsequent adaptations

Occupation: Criminal Gang Boss

The Problem: Takes advantage of poor desperate children and doesn’t give a rat’s ass about them. Also, kind of abusive.

Now you probably don’t want to work for a lot of bosses in many Dickensian works since many of them tend to be bastards who make bastards who make little kids work in horrendous conditions for starvation wages and aren’t held accountable to whatever damage they cause since these works were written in the 19th century. Let’s just say that out of all Dickensian bosses Ebenezer Scrooge is benevolent in comparison even before being visited by three ghosts on the night before Christmas. Bad as Scrooge may be but at least most of his employees were adults with desk jobs as far as the adaptations are concerned. Still, I have Fagin on the list because he’s basically a bottom feeder in an awful system. Now he’s the kind of representative criminal you’d find in the slums of Victorian England who would take in children who basically have no where else to go but either the workhouse or the streets and train them in pickpocketing and other illegal activities. Sure Fagin may teach these kids how to make a living but he’s also creating a legion of juvenile delinquents destined to go to very bad ends, thus making him a terrible role model. Also, he makes them steal for him and takes a share of the proceeds adding to his wealth. Not only that, he cares more about accumulating wealth and not getting caught than the welfare of those under his wing, especially those kids hanged by the authorities. And he also displays abusive behavior to those kids who don’t do his bidding like the Artful Dodger as well as throw others out who don’t perform up to snuff. Basically this guy is a bastard in more ways than one and the fact he’s a criminal who recruits children he unapologetically mistreats just makes it worse.

5. Franklin Hart Jr.

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From: 9 to 5

Occupation: Corporate Executive

The Problem: Corruption, incompetence, bullying, sexual harassment, sexism, and blackmail.

Dabney Coleman was the go to guy for corrupt corporate executives in the 1980s and this film is no exception. Of course, what stands out is that he’s a sexist pig in a workplace of mostly female employees. And it’s perfectly clear that many of them are more competent of running the company than he is, especially Violet Newstead who has great ideas Hart is willing to steal from, but isn’t willing to give her a promotion solely due to her sex. He hits on his married secretary Doralee Rhodes by spreading false rumors that they’re having an affair (though they are not) that results in her losing credibility in the office. Oh, and he cruelly yells at and threatens Judy Bernley after she made a mistake on her first day at work and fires another female worker over an overheard conversation on salary differences. And what’s worse is that Hart sees absolutely nothing wrong with any of it. You can see why Violet, Doralee, and Judy conspire to murder (and later kidnap) him and the office is a much better place after they do.

6. Jeff D. Sheldrake

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From: The Apartment

Occupation: Corporate Executive

The Problem: Being a top boss in a toxic corporate culture, rewarding employees for what they could do for him than actual competence, sexual harassment, corruption, and driving a female employee to try to kill herself.

Fred MacMurray may be best remembered by your parents as the father on My Three Sons despite the fact he was an utter turd in The Caine Mutiny and couldn’t keep it in his pants in Double Indemnity. In The Apartment, he’s an utter turd who can’t keep it in his pants with a family as well as a cushy senior executive job at any insurance company. Now C. C. Baxter’s is a man who’s so desperate to get ahead that he’s willing to let his superior executives use his apartment for their extra-marital proclivities. Unfortunately, this leaves Baxter with an undeserved reputation as a hard drinking womanizer and not much of a personal life outside his workplace. Despite his apparently nice facade, Sheldrake is basically the worst of the lot for not only does he promote Baxter on the condition that he use his underling’s apartment for his own affair but is also sleeping with Baxter’s crush an elevator girl Fran Kubelik who has a bad case of low self-esteem. And Kubelik is only one  in a long line of Sheldrake’s conquests who were all manipulated and lied to just so Sheldrake could get a little bit on the side. Sheldrake cares nothing about Kubelik and when his Christmas gift to her of $100 leads her to attempt suicide, he just spends Christmas with his family and has Baxter deal with the ordeal. Let’s just say if you have to choose between your career and love interest while working for this steaming piece of shit, go with the love interest.

7. Gordon Gekko

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From: Wall Street

Occupation: Corporate Raider

The Problem: Greed, corruption, has no concern to care or invest in employees’ well-being, abuse of power, bullying, and backstabbing.

Gordon Gekko is basically unrestrained greed personified and a man who truly loves capitalism above all else. Sure he may seem charming at first and may be wiling to show you the ropes of corporate finance. However, remember that while he’s great to work for when things are going well, he’s absolute terror when the deal goes bad and doesn’t give a damn about who he screws over or which employees he throws under the bus. All he cares about is making money, gaining power, and being rich, plain and simple. After all, he did say, “Greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through, and captures, the essence of the evolutionary spirit. Greed, in all of its forms; greed for life, for money, for love, knowledge, has marked the upward surge of mankind and greed, you mark my words, will not only save Teldar Paper, but that other malfunctioning corporation called the U.S.A” Gekko will claw his way to the top even if it means dirty dealing and insider trading or go to jail for trying while taking a few with him. And he’s not above berating his employees or resorting to physical force if he so chooses. Still, it’s no wonder that Michael Douglas cringes whenever he hears from stockbrokers how Gordon Gekko inspired them to become stockbrokers. Gekko may be seen as a financial role model for libertarians and people on Wall Street, but he’s a horrible man you wouldn’t want to work for as well as a horrible human being.

8. Lieutenant Colonel Nicholson

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From: Bridge on the River Kwai

Occupation: British Army Officer and POW

The Problem: Basically drives his men complete a building project as a morale building exercise, but ends up having his unit commit treason instead. Also driving his men to exhaustion in order to complete the said bridge. Having very skewed priorities.

Of course, being POW in a Japanese prison camp during World War II was a terrible experience for any soldier, especially in Southeast Asia since it involved a lot of hard labor in the jungle as well as sparse accommodations and torture. You can hardly blame Lt. Col. Nicholson for wanting to make things better for his men at the prison camp as well as try to build their morale. Nicholson is willing to stick up for his men as well has have the Colonel Saito conduct his camp in accordance to the Geneva Conventions. Yes, he has a lot of guts and means very well yet Nicholson thinks that helping the Japanese build a bridge for their railroad would be a great morale building exercise for his men and its completion would exemplify the ingenuity and hard work of the British Army for generations. And he’s willing to drive his drive his men to exhaustion to complete the bridge on time whether they like it or not. Unfortunately, Nicholson basically too consumed in the project to realize that he’s collaborating with the enemy and having his men commit treason against their own country at a time of war. I’m sure that once the war is over, his men are going to wish they would’ve fragged him or at least escaped with Shears when they had the chance. Despite that Nicholson isn’t a bad guy and may have redeemed himself by blowing up the bridge, his soldiers are going to remember him as a national disgrace and regret what they’ve done, especially if they’re being tried for war crimes back home. Nicholson should’ve just tried to escape or at least not have cared so much about building that damned bridge.

9. Hilly Holbrook

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From: The Help

Occupation: Housewife and Socialite

The Problem: Racism, thanklessness, entitlement, vindictiveness, and overall nastiness.

Now in being a black maid in segregation era  America was a very thankless job that pertained to doing housework for some white woman who saw their servants as less than equal. Minny Jackson has it incredibly bad under Hilly, a snooty and entitled bitch who treats her employees like disease ridden animals (as well as everyone else’s). She even insists that her maids use a separate bathroom and fires Minny for using her bathroom during a potentially deadly thunderstorm. Luckily Minny gets the last laugh by having Hilly eat her chocolate and feces pie. Minny’s successor Yule May Davis has it far worse since she ended up fired for stealing and pawning Hilly’s ring so she could have money to pay for her twins sons’ tuition that Hilly wouldn’t lend to her which was $75. Oh, and she has Aibileen Clark framed for stealing loaned silver cutlery and fired by her boss after Aibileen basically denounces her as the godless vindictive woman she is.

10. Margaret Tate

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From: The Proposal

Occupation: Executive Editor in Chief

The Problem: Sexual harassment, forcing an employee to marry her, blackmail, and abuse of power.

Now Margaret Tate may be a maniacal, insensitive, and annoying career bitch. However, she makes the list because she basically forced one of her employees to marry her when she’s under the threat of deportation. Sure this movie is a romantic comedy but making an employee marry you for whatever reason (or pretending to be engaged) whether expired Visa or not is an abuse of power. Oh, and it doesn’t help that she’s putting Andrew Paxton at risk for felony charges for immigration fraud that amount to a fine of $250,000 and 5 years in prison. Of course, to avert this means they have to go on a trip to meet Andrew’s family  in Alaska. Now Margaret and Andrew may live happily ever after as far as we know, yet we’re sure that having a relationship with your boss wasn’t much of a choice for Andrew. And it doesn’t help that he disliked her so much while working for her. This isn’t a great beginning to a beautiful relationship and if I had a male employer who tried to force me to marry him for whatever reason (even with blackmail), I would just quit my job, especially if I disliked the guy in the first place. Besides, I’m not sure if Margaret knew whether Andrew was seeing anyone in the first place, which also has its share of negative repercussions.

11. Colonel Nathan R. Jessup

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From: A Few Good Men

Occupation: United States Marine Corps Officer and Commander of the Guatanamo Bay Naval Base

The Problem: Being a trigger happy psychopath, showing no loyalty to his troops, having a volatile personality, hypocrisy, illegally ordering a murder, driving a subordinate to suicide, corruption, refusal to take responsibility, and abuse of power.

Now say what you want about Lt. Col. Nicholson but he’s practically a saint compared to Colonel Jessup who is just one bad guy running Guatanamo Bay almost akin to a Nazi prison camp. While Nicholson tried to do what he thought was best for his men, Jessup shows no honor and loyalty for his troops and would sooner have one physically punished illegally and so dangerously that he dies from the encounter which he covers up rather than send him away on point of principle. He also forces a subordinate to forge a transfer order of a murdered marine which leads the guy to commit suicide before he could testify against Jessup in court.  And even when Jessup admits to directly ordering an illegal “Code Red” disciplinary measure, he feels incensed at being held responsible for it and feels that he’s totally justified in what he’s done. Sure he may give a great speech like “You can’t handle the truth!” and talk about how it’s supposed to be the duty of the strong to protect the weak, but he basically betrayed when he had  a kid brutalized and accidentally killed for being weak. If your commanding officer is like him, I suggest you file for a transfer immediately before he orders you to do something that could get you court-martialed. And if transfer wasn’t an option, you might want to opt for a dishonorable discharge on insubordination since the most popular court-martial defense is “I was just following orders.”

12. John Milton

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From: The Devil’s Advocate

Occupation: Attorney

The Problem: He’s basically Satan and technically evil. Also, corruption, murder, and nepotism.

The aptly named John Milton is basically the devil in the flesh in this 1997 film in which he runs a corrupt, high-powered, and multinational New York City legal office with global connections called Milton, Chadwick & Waters which is composed of immoral humans and his own demons. Of course, many of these lawyers they also happen to be his kids to all kinds of women he raped, including Kevin Lomax himself. And he hopes that his kids would mate with each other and produce the Antichrist. However, he’s not above bringing out the worst in his legal employees and his influence has Kevin transform from a simple country lawyer to a highly corrupt and morally dissolute New York City attorney that would make the cast of Boston Legal seem like a church choir. And as for Lomax, working for the devil, he becomes engulfed in demonic forces that ruin his career and drives his wife to madness and suicide. Oh, and he uses his legal firm to exploit the legal system to get as many violent criminals off the hook and spread corruption all over the world, hoping that Earth would become such a perversion that it will hurt Heaven and God. Also, tends to kill any of his employees who threaten to expose him. Basically he’s a literal boss from hell.

13. Patrick Bateman

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From: American Psycho

Occupation: Wall Street Investment Banker and Corporate Executive

The Problem: He’s an absolutely competitive and a complete psycho with rather disturbing fantasies. Also has a lot of addictions and is inflicted with conspicuous consumption.

Sure he may be played by Christian Bale and seem rather charismatic and friendly with a taste in designer clothes. However, as to why anyone would want to work for him or with him is anyone’s guess. And it doesn’t help that his gay colleague and his secretary are both in love with him. Bateman has the distinction as one of the most believable psychopaths in film and has scored hire on the APD/sociopathy checklist than the Joker or Hannibal Lecter. To put a long story short, Bateman is a rich, shallow, yuppie type who’s addicted to sex, drugs, and conspicuous consumption. Yet, he has another hobby on the side which is killing (and sometimes raping) people whether it be colleagues, prostitutes, or the homeless. Also, he could kill his colleagues (or subordinates) for some of the stupidest reasons whether it be over a business deal nobody knows about in detail, having a better business card than him, and being able to get a reservation at a popular restaurant. Oh, and he’s willing to sarcastically confess his crimes and sociopathy to fellow colleagues which nobody seems to take seriously. And he tries to murder his secretary with a nail gun when she finds a journal depicting his grisly rapes and murders. I’d rather be unemployed than work for such a racist, sexist, homophobic, and extremely elitist selfish killing machine. This is especially true if he’s a fan of Huey Lewis & the News.

14. Meredith Johnson

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From: Disclosure

Occupation: Corporate Executive

The Problem: Sexual harassment, abuse of power, attempted rape, and backstabbing.

Despite being played by Demi Moore, Meredith Johnson is the worst boss you’d ever want to be involved in a relationship with, especially if you’re her ex Tom Sanders. Right from the time she’s promoted to CEO of DigiCom (a job that Tom probably should’ve had), Meredith aggressively tries to resume her romantic relationship with Tom despite that he’s now married family man and repeatedly turns her down. Yet, Meredith doesn’t seem to care and even forces herself on him though Tom ends up spurning her and pushing her to the ground. In revenge for not having sex wit her, Meredith tries to ruin Tom’s life and career for suing him for sexual harassment and later tries to make him a scapegoat for the recent problems with the quality of the company’s products. And for a while, it seems that Tom is screwed since nobody in his company believes what Meredith was doing to him. It’s basically what you get if the lady from Fatal Attraction was your boss, well, sort of. Still, if Tom had given in, his marriage would’ve been over and Meredith still would’ve sued him for sexual harassment anyway.

15. August Rosenbluth

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From: Water for Elephants

Occupation: Circus Owner, Ringmaster, and Head Animal Trainer

The Problem: Cruelty to animals, abuse, bullying, and intimidation.

He may seem charming and kind at first but he has a vicious streak a mile wide. This guy is an animal slave driver who’s willing to drive his four legged performers to exhaustion and injury since he believes that the suffering of animals is nothing compared what people go through. He’s not so much nicer to people since he expects his animals and employee to follow his orders to the very letter. And he’s not afraid to throw people from the train who disobey him or beat the shit out of them. Oh, and he’s possessive and physically abusive to his wife and if you try to run off with her, he’ll go to great lengths to make sure you’re dead even if he has to send two thugs to beat you up. Let’s just say, nobody wouldn’t be upset if he got trampled by an elephant on any given day.

16. E. Edward Grey

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From: Secretary

Occupation: Attorney

The Problem: Sexual harassment, taking advantage of employee’s insecurity, and abuse of power.

Now this movie is basically what 50 Shades of Grey would be as a workplace romantic comedy. Of course, E. Edward Grey may not be an abusive psycho boyfriend like Christian Grey would be, but he’s not a great guy to work for. Sure engaging in consensual BDSM may be all right but basically hiring a legal secretary for that very purpose and firing her after engaging in sexual intercourse isn’t whether having sexual insecurities or not. Of course, this is especially true if the sex was basically his idea in the first place, which is sexual harassment. And it doesn’t help that Lee Holloway had just been released from a psychiatric hospital after an episode of self-harm, which almost makes Grey seem much worse. Also, I’m not sure the power dynamic in the workplace is a great foundation for a healthy relationship in the bedroom, BDSM or not.

17. Pontius Pilate

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From: Monty Python’s Life of Brian

Occupation: Roman Governor of Judea

The Problem: To make a long story short, he’s basically an idiot who no one could take seriously, not even his employees. Also incompetence, no sense of humor, and being easily offended.

Now Pontius Pilate was a bad boss in real life as testified by Josephus as well as Philo of Alexandria and the fact that he was recalled to Rome because the Romans thought he was too brutal. Yet, to the extent he’s depicted as a jerk in the Bible and biblical movies kind of depends on interpretation. Yet, he’s portrayed as a guy reluctant to crucify Jesus in the Gospels because the writers didn’t want to depict the Roman authorities in a negative light. In Life of Brian, Pilate is basically an idiot who no one could take seriously especially since he has trouble pronouncing the letter “r” which the crowd of people goes to great lengths to ridiculously exploit just to make fun of him. The scene when the soldiers bring Brian to him is particularly relevant of his ineptness as well. It’s obvious that the guy has no sense of humor and is easily offended when his soldiers laugh whenever he mentions the name of his friend in Rome, “Bickus Dickus.” Of course, the soldiers obviously view such moniker as a joke name, a concept that Pilate has no understanding. Yet, he ends up sending one of his soldiers to gladiator school after not being able to keep himself from laughing at the name “Bickus Dickus” which seems pretty harsh. Still, Pilate’s foolishness and lack of any sense of humor basically keeps the Roman soldiers from doing their jobs and inadvertently helps Brian escape.

18. Daniel Plainview

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From: There Will Be Blood

Occupation: Oil Industrialist and Tycoon

The Problem: Workplace endangerment, abuse of power, disdain for humanity, alcoholism, bullying, corruption, murder, and others.

Of course, this movie is about the contention between two guys the audience will despise but at least the self-centered religious preacher has nobody working for him even if he bullies his dad and manipulates his flock and ultimately sells his soul to Daniel Plainview in the end. Daniel Plainview, on the other hand, may be a determined boozy miner who just wants to earn a living or basically do whatever it takes to get a buck even if it means stepping on everyone he needed to in order to advance his own goals as well as exploit everyone in the film with a speaking role. Yet, he’s indifferent to life and has no qualms about cheating folks in California who basically work like oxes and give him oil to sell. Too bad for them, a few of them fall victim to occupational hazard including Plainview’s adopted son H. W. who goes deaf by the sound of an oil well. Of course, you can bet that these workers’ families won’t get much compensation as far as Plainview is concerned. He also personally kills a few people, abandons his son who… failed him, takes general pleasure and dominating everyone, and perceives the world as much more evil than he is. Still, Plainview can’t care less about those who work for him and bring him wealth and is willing to fake care through his manipulation to outright bullying. And even his adopted son H. W. is seen is merely a prop to him that he uses to create a pretty face to help him make business deals. Let’s just say, you don’t want to work for this guy, especially when he starts to lose his sanity.

19. Jonathan Shields

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From: The Bad and the Beautiful

Occupation: Movie Producer and Studio Mogul

The Problem: Forming relationships with employees whom he’s perfectly willing to use as tools that can be disposed of. Also, tries to toy with his workers’ personal lives just so he could make a movie. Not to mention, he’s kind of a perfectionist, control freak, and backstabber to the max.

Jonathan Shields loves movies and loves making them though he cares more about the quality of his films than his human relationships. In fact, he basically uses his relationships as a means to an end, whether it means being buddies with a director when they were first starting out, hooking up with an actress she wants in his film so she won’t spend her spare time drinking or sleeping with other men, and taking a screenwriter on vacation with him so the guy won’t have to be distracted by his wife while he’s writing. Yet, once he’s done with them, he ends up basically stabbing them in the back whether it be by denying his director buddy a chance to make the film of his dreams, having his girlfriend walk in when he’s screwing another actress after celebrating her success at the premiere after party, and not telling his screenwriter that he inadvertently left the guy’s wife run off with an actor that later leads to them both dying in a plane crash. Sure he screwed these three people to the ground leaving no small wounds, but all three were better off achieved greater success because of him. Of course, you can basically call Jonathan Shields an unpolished turd with the Midas touch yet even if he did help your career, you’d still be bitter of how he hurt your feelings by screwing you over.

20. General Boulard and General Mireau

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From: Paths of Glory

Occupation: Generals in the French Army

The Problem: Basically these two guys are disconnected from the reality of the trenches and basically ordering what amounts to a suicide mission. Punish a whole regiment by having 3 soldiers shot at random for cowardice. Also, abuse of power and inability to take responsibility for their failures.

World War I was a terrible war with many losses resulting in the upper brasses disconnect with what the soldiers are really facing and the deadly results it led to. In fact, Mireau basically doesn’t believe that there’s such a thing as PTSD as well as orders his artillery to bomb their own trenches and that both of these guys are staying in fine housing accommodations while anyone who’s not a general is basically having to reside in vermin infested quarters. These two generals are basically epitomes of this when they order Colonel Dax and his regiment to attack the Anthill which is a suicide mission, a fact that’s apparent to every soldier in the regiment. Yet, when Dax’s soldiers’ common sense overrides their willingness to obey orders during the actual attack, these two guys refuse to acknowledge their responsibility just to save face and preserve their quest for personal glory. In fact, they basically punish Colonel Dax’s regiment by having three of his soldiers court-martialed and executed for cowardice by firing squad. Of course, the two generals have made sure that the court-martial is a kangaroo trial and that these three condemned men are doomed to die for no reason at all.

21. Lord Raglan, Lord Lucan, and Lord Cardigan

From: The Charge of the Light Brigade (1968)

Occupation: Generals in the British Army and Aristocratic Peers

The Problem: These three guys are incompetent upper class twits, inability to work together, have no concern for their men, and other factors that led a major miscommunication and one of the biggest military disasters of all time.

Now these three guys were just as bad bosses in real life as they are in this movie due to the systematic problem that these guys basically purchased their own commissions. Yet, while Raglan is the least worst of the bunch he’s more or less incompetent who was just promoted beyond his ability yet ordering Lord Cardigan to lead the Charge of the Light Brigade and promoting Lord Lucan over him weren’t very good ideas. Yes, they were brothers-in-law but they absolutely detested each other and neither were very bright in the least. Seriously, Cardigan was described by historians as, “an overbearing, hot-tempered fool of the most dangerous kind in that he believed that he possessed real ability.” In the movie, Cardigan also tends to treat his troops like personal property. And when Lucan received Raglan’s order, he basically ordered Cardigan to charge his men through a gauntlet of fire to capture the guns at the far end of the valley. The result was that the Light Brigade was driven off by overwhelming enemy numbers and they retreated through the same way they charged leading to 278 British casualties and nothing accomplished. Oh, and right after the charge, Cardigan basically has lunch on his yacht and tells the survivors that the disaster wasn’t his fault. So there you have it, the Charge of the Light Brigade was a disaster due to incompetence, mutual jealousy, and miscommunication between these three guys who make desertion seem like a viable option if any of them were your commanding officer.

22. Tony Stark (a. k. a. Iron Man)

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From: The Iron Man Series

Occupation: Billionaire, Superhero, Tycoon, Inventor, and Philanthropist

The Problem: Egotistical, high maintenance, immature, selfish, and basically has his assistant do everything.

If you think having Iron Man as your boss would be cool, then prepare to be disillusioned if you’re hired to be his personal assistant. Stark is basically a big baby with a huge ego and lots of expensive toys who’s horribly dependent on Pepper Potts for basically everything from running his company, organizing his schedule, making excuses for him, installing a personal arc reactor to keep his heart beating every once in a while, and calling the contractor every time Stark blows up his workshop. Pepper Potts may have a job that pays well, but unfortunately this means her whole life basically revolves around Tony Stark and basically has no time for anything else. Also, her job must be incredibly stressful and bound to drive any normal person insane. Tony must be lucky that he has such a dedicated assistant willing to put up with all his hijinks and activities simply out of being in love for him. Yet, how she manages to keep Tony’s life in order while being able to retain her appearance and take proper care of herself, I have no idea.

23. Miranda Priestly

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From: The Devil Wears Prada

Occupation: Editor in Chief for a Fashion Magazine

The Problem: Demanding, abrasive, verbally abusive, and being a major control freak.

Working in fashion must be one of the most nightmarish fields for most women, especially since it’s one that’s shallow and pertains to ridiculous clothing. Compared to other bosses on the list, Miranda isn’t as bad as many of the bosses on the list. I mean she’s not physically abusive, gets people killed, commits crimes, or sexually harasses her employees. Also, she’s perfectly capable of doing her job. Yet, she’s a real pain in the ass who terrorizes and insults most of her staff, including Andy Sachs. She is a major control freak who oversees every aspect of the magazine at every stage of production and thinks nothing of turning everyone else’s schedule around while micro-managing her own. She also likes to use Andy as a punching bag by hurling insults at her about her weight, criticizing her writing, and assigning her to do impossible tasks which greatly takes a toll on her personal life. And she also seems to take positive relish in it. It’s a wonder why people are willing to work for her and not go insane. Also doesn’t tolerate anyone who disagrees with her.

24. Calvin Candie

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From: Django Unchained

Occupation: Planter

The Problem: He’s a sadistic slave owner who has his charges fight for the death for his own enjoyment as well as having a slave being murdered by dogs as well as other dastardly deeds. Also, racism and intimidation.

Slavery was a brutal institution that put blacks as inferior to whites as well as be seen as having no rights of their own and doomed to involuntary servitude. It wasn’t unusual for a slave owner to be an abusive rapist as well as torture his or her slaves on a regular basis. Still, while he may be played by Leonardo DiCaprio, Candie may seem charming at first but he’s actually a sadist who seems to inflict violence on his slaves for a lot more reasons than just keeping them in line. In fact, he seems to be very insensitive to it and seems to get pleasure in seeing two slaves fight each other to the death or casually letting a slave unwilling to fight get torn apart by dogs, which sickens even the most hardened bounty hunter Dr. King Schultz. Still, he’s a complete monster even by slave owner standards and Candyland is basically a plantation of horrors. Let’s just say that slave owners would’ve thought twice about having their own slaves fight each other or having a runaway ripped apart by dogs, especially since they were substantial financial investments. Putting slaves in gladiatorial battles just wouldn’t make any sense to an antebellum slave owner. You could see why King Schultz had to shoot him in the chest when Candie offered to shake his hand.

25. Idi Amin

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From: The Last King of Scotland

Occupation: Military Dictator of Uganda

The Problem: Basically he’s a ruthless dictator who was responsible for killing as many as 500,000 people. Robbing his countrymen and not taking being cheated on well despite having 3 wives. Also being batshit insane.

Working for a dictator is no fun at all. In fact, dictators make really terrible bosses in general, especially if he goes by the name of Josef Stalin. Idi Amin is no different and though he may seem charming at first but remember this is one of the more notorious African dictators as well as responsible for genocide during his 8 year rule of Uganda. Also, he’s one of the few famous dictators to have a feature film about his rule which is depicted so menacingly. By sharing his love of Scotland being impressed at his ability to shoot a cow, he manages to charm Nicholas Garrigan into becoming his personal physician and help modernize Uganda’s health care system.. Yet, working for a genocidal dictator has a lot of strings attached such as having to rationalize your boss’s crackdown of the opposition and expelling South Asians out of the country. Also, the fact that Garrigan can’t keep it in his pants and ends up knocking up one of Amin’s wives. Still, let’s just say you don’t want to work for a guy who isn’t above beating you up or hanging you up on a meat hook by your skin, no less. Let’s just say I’d rather work for Darth Vader than this guy.

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