Some of The Most Memorable Fictional Bosses

Posted by Brian Morell

Do you dread going to work because you have the supervisor from hell? Would you treat your manager like royalty if you could? Are you your own boss? Or just boss in general?

Whatever it is, pick your reason to celebrate today since October 16 is Boss’s Day, even if it’s just to get on your boss’s good side! Here are some of the most, well, let’s call them memorable bosses!

The Narrator from Bartleby, the Scrivener: The ultimate in weak-willed and passive aggressive bosses, the narrator is a lawyer who handles business agreements, overseeing a couple of scriveners. Due to increase in work, he needs to hire another assistant, eventually taking on the titular Bartleby for the position.

At first, Bartleby seemed to be a great employee, but he soon refuses to do tasks, stating, “I would prefer not to.” Instead of firing Bartleby, the narrator comes up with passive-aggressive ways of dealing with him, including moving his entire business elsewhere. While Bartleby became increasingly disillusioned and steadfast in his refusal to do anything, including eat, the narrator proved to be someone that could not handle confrontation of any kind.

Bill Lumbergh: From the mind of Mike Judge, Office Space portrays office life as mind-numbing, soul-killing work. Sadly, the satire rings too true, especially with the layers of ineffective bosses and other busy-bodies around. But no one generates more ire than Bill Lumburgh, played by Gary Cole, in all his brilliant smugness.

His “ahs” and “ums” are just a prelude to his useless babble. Even if you try to duck out early on a Friday, you are bound to hear “What’s happening? Ummm, I’m gonna need you to go ahead come in tomorrow. So if you could be here around 9 that would be great, mmmk.” Plus, he wears suspenders and a belt simultaneously. Talk about evil!

Mr. Burns: Speaking of being a terrible baseball manager, C. Montgomery Burns has proven time and time again that he is one ultimate bad boss. Owner of the Springfield Power Plant, a workplace of questionable safety, over the years Mr. Burns took away the union’s dental plan and had a rather interesting wardrobe, including a vest made from real gorilla chest.

If you disagree and think Mr. Burns is a good boss, I think it’s time to release the hounds!

Boss from Hell from Brad Starks on Vimeo.

Mr. Tarkanian: If you think your boss is bad, ask yourself this: has your boss ever stabbed you or a co-worker over 30 times using a trident? If no, then you must be thankful that Mr. Tarkanian isn’t your boss! In this Saturday Night Live skit, Will Ferrell as Mr. Tarkanian is about to hire a new employee, played by Pierce Brosnan, but before it is official, Mr. Tarkanian shows what kind of boss he really is.

You would be working for the fourth best in-flight magazine, but you need to decide if that is worth, as Mr. Tarnkanian put it, “me, kicking you ‘til there’s blood in your stool.” The choice is yours!

Liz Lemon: Ok, maybe there is a portrayal of a flawed, but ultimately well-meaning boss in Liz Lemon on 30 Rock. She’s actually a good boss, if you overlook her tendency to be selfish, neurotic, and self-obsessed. Being a middle manager, she is in a tough position, having to reign in a group of writers and actors who have their own countless problems while simultaneously fighting for those people and the success of her show with her boss/mentor, Jack Donaghy.

Despite what obstacles may be in her way, whether the possibility of her staff getting laid off or that someone she works with ate her sandwich, Liz Lemon usually makes the right call. Eventually.

Do you have a story about a boss you’d like to share with us, good, bad, or otherwise. Let us know about them in the comments!

Brian Morell is an awesome librarian from New York City. He writes about his travels and life at That Long Yellow Line and about music for The Ruckus. Follow him on Twitter @goodinthestacks.