A rainy-ish day like today calls for a fun post.
While we all at some point might complain about our bosses, they certainly can’t be as bad as those villainous fictional employers that we have all grown to love. So next time you’re feeling belittled by your boss, ask yourself if they’re any worse than those who made our list of the top 25 worst fictional bosses.
25. Michael Scott – As the fictional regional manager of
the Scranton branch of Dunder Milflin
, Michael Scott insists everyone in the office think of him as a friend first, a boss second, and probably an entertainer third. Often seen carrying a “World’s Best Boss” mug (that he purchased for himself) and often substituting subordinates as friends and family members in place of the friends and family he does not have, Michael truly believes that an office is the "place where dreams come true."
24. Karen Walker – When it comes to patronizing one’s
employees Karen Walker 
(Megan Mullally) from Will and Grace doesn’t disappoint. She believes that her live-in housekeeper, Rosario doesn’t speak English so when Karen barks orders at her she adds the letter "o" to the end of every word. Karen also went as far to arrange for Rosario to marry her best friend, Jack despite his homosexuality, so that Rosario could obtain a green card to remain in the
United States and most importantly remain Karen’s maid.
Despite the fact that Karen and Rosario are constantly
yelling at each other, they truly have a love-hate relationship.
23. Justin Pitt – Elaine Benes’ boss on the TV sitcom, 
Seinfeld. Elaine was Mr. Pitt’s personal assistant until a series of coincidences caused him to believe that Elaine was trying to kill him. Elaine was better off though as Mr. Pitt’s aversion to fountain pens and the quest for the perfect sock often kept her from engaging in shenanigans with Jerry, George, and Kramer.
22. Nigel Wick – Mr. Wick, better known as Drew Carey’s
boss on the Drew Carey show was always boisterous and
offensive, which is no
t surprising being that he was played by late night talk show host Craig Ferguson. Mr. Wick was known to inappropriately insert himself in the private lives of his employees—not only did Drew have to marry Mr. Wick in order for Wick to receive a green card, but he also had his own special criteria for firing employees, for instance if you’re last name was “Johnson” you were fired.
21. Russell Dunbar – Portrayed by David Spade on the CBS
sitcom Rules of 
Engagement, Russell works for his father’s company, so he has no real responsibilities except to torture and demean his assistant Timmy who holds an MBA from Oxford University. Timmy describes Mr. Dunbar as “a disgusting cad with a possible sex addiction” and Timmy looks forward to finding a new position once the economy rebounds.
20. Cosmo Spacely – Mr. Spacely is president of 'Spacely
Space Sprockets', where George 
Jetson is employed. Mr. Spacely can frequently be found yelling at George for his poor work performance and is best known for yelling, “JETSON!!!!” and “YOU’RE FIRED!!!!” usually in the same sentence. He has been known to meddle in George’s personal life in order to add to Jetson’s already high stress levels.
19. Ari Gold – Ari Gold (Jeremy Piven) is one of the most
powerful agents in Hollywood on HBO’s hit series, Entourage. Despite the fact that he’s demanding and verbally abusive to his long-suffering assistant Lloyd, Ari’s constant jabs have made Lloyd the great agent he is today.
18. Julius C. Dithers – Mr. Dithers is Dagwood’s boss in the 
comic strip Blondie. In addition to his harsh personality, Dithers is portrayed as a difficult and controlling employer—he always denies Dagwood’s requests for pay raises and is continually threatening to fire him.
17. Bill Lumberg – Unsyphathetic Initech Vice President,
Bill 
Lumberg (Gary Cole) is known to be a stickler for paperwork and is in constant need of his employees to come into the office on Saturday. Lumberg’s character in the cult film, Office Space is a perfect satire of soul-crushing corporate America.
16. Sue Sylvester – While Sue isn’t always the boss, she
has stepped up due 
to some clauses in her contract that made her principal of the fictional McKinley High School on the hit television show, Glee. Coach Sylvester is a bully to students and teachers alike and will do anything to keep her cheerleading squad in the limelight. She’ll do whatever it takes to win, even if she has to “prostitute herself or engage in inappropriate behavior with minors.”
15. Jeff Sheldrake – Mr. Sheldrake, played by Fred 
MacMurray in The Apartment, is probably the worst personnel director of all time. Not only does he have multiple affairs with his female employees, but he also promotes CC Baxter (Jack Lemmon) on the grounds that
he can use Baxter’s apartment for his latest fling.
14. Franklin Hart Jr. – Dabney Coleman brought Franklin
Hart Jr. to life on the big screen in 9 to
5 as Consolidated Companies’ resident sexist, egotistical, lying, hypocritical, bigoted boss whose death is fantasized about by the team of women he manages at the office. But when one of the fantasies comes true—hilarious consequences ensue as the women realize this is
their chance to turn things around.
13. Blake – While Mitch and Murray were probably the
worst bosses of all time, Blake from Glengarry 
Glen Ross, portrayed by Alec Baldwin was their lackey brought in to motivate their salesmen by pitting them against one another. And as we all know nothing makes you feel more appreciated than a good motivational message from your boss, “We're adding a little something to this month's sales contest. As you all know, first prize is a Cadillac Eldorado…Second prize is a set of steak knives. Third prize
is you're fired.”
12. Montgomery Burns – Best known as the evil owner of 
the Springfield Nuclear Power Plant and Homer Simpson’s boss, Mr. Burns is a stereotype of corporate America, which is demonstrated through his constant desire to increase his own wealth and power and inability to remember his employees' name. Burns uses his wealth to do whatever he wants and can frequently be found
tormenting the inhabitants of Springfield.
11. Professor Callahan – This sleazy attorney/law
professor at Harvard University nurtures
Elle Woods’ (Reese Witherspoon) inner lawyer in the 2001 comedy Legally Blonde. After an impressive performance in court, Callahan invites Elle to “discuss” her future as a lawyer, but when she rejects his sexual advances she begins to doubt her career choice altogether.
10. Ebenezer Scrooge – The principal character in
Dickens’ A Christmas Carol, 
Ebenezer Scrooge is a cold-hearted and greedy man who hates Christmas and treats Bob Cratchit (aka Mickey Mouse or Kermit the Frog depending on the version you’re watching) like garbage. Even though he does not have enough money to feed his family Christmas dinner—Cratchit remains loyal to Scrooge
despite his wife’s protests.
9. Margaret Tate – In the movie The Proposal, Canadian
book editor, Margaret Tate played by Sandra 
Bullock needs a green card in order to stay in the country and keep her job, so she blackmails her assistant Andrew (Ryan Reynolds) to marry her in exchange of Andrew being promoted to editor and having his own book published.
8. Miranda Priestly – This fictional editor-in-chief of
Runway magazine from the feature film, The 
Devil Wears Prada, is best known for her icy demeanor and the emotional and psychological abuse she thrusts upon her personal assistants that might as well be walking through a revolving door. “Loosely” based on real life Vogue editor-in-chief, Anna Wintour, Priestly takes the cake or
should I say steak when it comes to ice queens.
7. Wilhelmina Slater – Many of the woman on this list are
involved in the fashion industry, I guess 
when they say that fashion is cutthroat they’re right. Wilhelmina, portrayed by Vanessa Williams in Ugly Betty is a conceited, self-absorbed former supermodel turned creative director of fictional fashion magazine, MODE. When she is overlooked for the job of editor-in-chief, she does everything from lie, cheat, steal, and kill to land the job, ruining any one that gets in her way, including her loyal assistant Marc. Wilhelmina is the perfect example of what is beautiful on the outside is not always beautiful on
the inside.
6. Gordon Gekko – This corrupt corporate raider, is a
dishonest Wall Street player 
who values the almighty dollar above all else as demonstrated in his famous speech about greed. Portrayed by Michael Douglas in both Wall Street and Wall Street: Money Never Sleeps, he only sees companies and employees for their financial value and will do anything to get ahead.
5. Meredith Johnson – DigiCom president and former love 
interest of Tom Sanders (Michael Douglas), Johnson (Demi Moore) is a true B-word when she files false sexual harassment claims against Tom in the book/movie Disclosure. With everything to lose, Tom’s life will be ruined if the claims are believed to be true.
4. Cruella de Vil– Cruella de Vil certainly deserves a spot on our list of horrible bosses, after all her name is a play on the words “cruel” and “devil” and she is 
just that. She is best known for her elegant furs and she certainly gives a new meaning to killing for fashion—any animal that can be turned into something sheik is fair game, including her employee, Anita’s Dalmatian puppies.
3. The Emperor Palpatine – While Darth Vader is commonly
regarded as a 
synonym of evil, he is nowhere as evil as his boss—The Emperor, Palpatine. The Emperor, also known as Vader’s Sith Lord [spoiler alert, eh, if you haven’t seen Return of the Jedi by now, that’s your problem, anyway…] forces Vader to seduce his son, Luke to come to the dark side, but when Luke refuses and is overtaken by The Emperor,
Vader overcomes the dark side of the force and steps in to save
his son—killing Palpatine and realizing just how evil The Emperor
was.
2. Frank Costello – Jack Nicholson, portrayed sadistic Irish
mob boss, Frank Costello in the Oscar 
winning Scorsese film, The Departed. Costello, trains young Colin Sullivan (Matt Damon) to become his mole inside the Massachusetts State Police, but when Costello believes there’s a rat in his own organization he has Sullivan on the prowl to find it. The film ultimately ends with several
of Costello’s men dead—all I’m saying is if you’re not a police
officer, a member of the military, or a secret service agent,
and there’s a high likelihood of dying for your boss, you’re
boss is probably not a good person.
1. Michael Corleone – Also known, as the 11th most Iconic
Villian according the American Film 
Institute, Michael Corleone becomes the head of the Corleone family after his father’s retirement and his brother’s murder in The Godfather trilogy. Not only did he have his brother-in-law killed and divorced his wife all for the business, he’s a mob boss so that’s probably one of the worst kinds. But if killing your brother-in-law and divorcing your wife is not dedication to one’s job, then I don’t know what is.
So next time you’re hating your boss, just imagine if you worked for one of the above. Also, let us know if you think we’ve missed a fictional boss that deserves a spot on our list!
force—in fact I’m not even sure I can name them all, but I can tell you that my favorite couple is Pam and Jim (cliché I know).
