Horrible Bosses and Their Fashionable Staff That Deserved Better

What makes a bad boss? Someone who is a narcissist, a bully, who believes they are always right, terrible listener, micromanagers, credit stealers, no respect for their staff, harassers, the list is endless unfortunately. How can we spot one? Look for references in entertainment as examples of who do not deserve someone like you working for them. Below are four of the worst bosses in fictional entertainment history and their fashionable staff that deserved better:

  1. Miranda Priestly The Devil Wears Prada (2006)

Let’s discuss Emily Charlton- the assistant that always deserved better.

Unlike Andy who was VERY ungrateful and always thought she was above the work, Emily was hardworking, dedicated, and sacrificed to work for Miranda. She gave 100% every day, never questioned, and was dressed to the nines as she did it. For Miranda to replace Emily with Andy (who did not even care about the Paris trip) was heartless and showed she had ZERO respect for anyone who worked for her. Emily is an underappreciated character and deserved WAY better than the entitled Andy and heartless Miranda.

2. Ari Gold Entourage (2004)

Let’s discuss Lloyd Lee the assistant with the patience of a saint.

As Ari’s assistant, he was subject to a demanding and verbally abusive boss; Lloyd’s sexual orientation and ethnicity often fueled Ari’s tirades against him. Through it all Lloyd remained loyal, persistent, and calm when Ari was in a crisis. With his flair on the typical office menswear he did all this with ease, positivity, and genuine affection for the boss that abused him. He deserved a boss that was as caring as positive as he was. Ari was LUCKY to have him- at least being the horrible boss he was he finally recognized Lloyd’s value toward the end. Like most horrible bosses it was NOT soon enough.

3. Don Draper & Roger Sterling Mad Men (2007):

Now let’s discuss Peggy Olson and Joan Holloway- successful, fashionable women who were smarter than their male counterparts but stuck in a time where suits and bourbon drinks reigned supreme.

In the series premiere, Don walks right past Peggy, instead greeting only Joan, so the first time Don and Peggy talk, she’s waking him up from a nap. He does not even acknowledge her- why? Simply because she is not perceived as “sexy” and therefore not in his orbit. While they eventually develop a platonic repertoire here and there he still shows his chauvinistic lack of appreciation for her. In the later seasons he tells her “What do I have to do for you? Every time I turn around, you have your hand in my pocket,” he screams. “There’s not one thing you’ve done here that I couldn’t live without.” “Stop asking for things,” he says. Peggy was a smart go-getter that used her creativity and intelligence to get ahead rather than her sex appeal. However, being Don Draper every so often he had to “put her in her place.” She would be running Sterling Cooper in 2020.

Joan has the blessing and the curse of being what most would consider a beautiful woman.  Every man she encounters seems to see her only as a vehicle for his own desires. Her ex-husband is an incompetent doctor who raped her. Her coworkers encouraged her to sleep with a client to gain an account. Don’t even get me started on her affair with Roger! In Season 1, Roger says he’s even contemplated leaving his wife, although he would like to “lock her up for a week,” implying he would like her all to himself. It was like she was conditioned to believe she was a beautiful object to possess rather than a valued partner.

Maybe if Don and Roger spent less time smoking, drinking, and whoring they would realize having a smart female beside them is an asset not an accessory.

4. Professor Callahan Legally Blonde (2001)

Now lets discuss Elle Woods, Vivian Kensington, and Brooke Taylor Windham. Three smart, head strong women who were way too good for a person like Professor Callahan.

Brooke was a smart, successful, entrepreneur in her own right (I wish they had her exercise classes in the movie!). However, when Callahan is discussing her defense all he can discuss is her rich deceased husband’s wealth and age. Like she didn’t have an empire on her own????? He just assumed that she needed a man to help her get it. While she is not part of Callahan’s staff, she is worth a mention as his treatment of her is beyond sexist and needs to be talked about. And I absolutely need that newspaper fitted blazer!

Take Vivian, while at first not the most likable character you can see she is slowly ignored more and more. Why??? She is just as smart as Elle, just as capable as Elle, but because she is not a “blonde bombshell” she is the one forced to get Callahan’s coffee and donuts??? She had an intelligence that matched the smarts of her collared shirt and sweater combos and she deserved more.

We can’t possible talk about Callahan without talking about Elle. Throughout the whole movie she is fighting the beautiful women are dumb stereotype. She starts to gain confidence in her smarts as Callahan seemingly recognizes her intelligence. She is actually believing she is not the “dumb beautiful blonde” everyone told her she was and should be . Even her parents in the beginning of the movie urge her away from the “boring” profession of law and to focus on winning local beauty pageants. All this confidence is thrown out the window the minute Callahan hits on her. It’s like she was transported back to that day when her parents told her not to pursue law. As we all know she pushes ahead and shows all you can be beautiful and smart- SHOCKING THAT WOMEN CAN BE CLASSIFIED AS MORE THAN ONE THING ISN’T IT???

Remember, before you take the subway in those uncomfortable shoes and your newest pencil skirt/shirt combo make sure your boss is worth your smarts, your loyalty, and your dry cleaning bill.

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