ON THIS day in 1962, “National Boss’s Day” was officially proclaimed, four years after Patricia Haroski registered it with the US Chamber of Commerce. Since then, it has been celebrated as a day to show appreciation for bosses who keep us gainfully employed. Of course, not all of them are praiseworthy. Still, they’re like family—you can’t live with them, you can’t live without them.
In honor of all supervisors, managers and executives who make or break our day, here are fictional bosses ranging from the boss-zillas to the ones we’d be more than happy to work with IRL (in real life).
Miranda Priestly, “The Devil Wears Prada”
Merciless and mercurial, Miranda is the editor-in-chief of a high-end fashion magazine. Revered but also feared, she reminds us of that boss whom we’d bend over backward for just to please. You don’t like her but you want her approval which is rare because she barely says a word to you save for sarcastic one-liners. Even if you do something right, she remains icy.
Margaret Tate, “The Proposal”
Uptight and controlling, Margaret is a monster who has no semblance of a life outside the office, treats her employees like her personal slaves and is likely to end up alone on her deathbed—her ex employee’s words, not ours.
Tony Stark, “Ironman”
Tony Stark is a man of his word, a “genius, billionaire, playboy, philanthropist.” A leader in every sense of the word, he finds new ways to improve his company to benefit not just himself but everyone else. Not all would use his wealth and tech for the common good and yet here he is.
Jordan Belfort, “The Wolf of Wall Street”
Debauchery could very well be his middle name. A stockbroker who runs a firm on Wall Street, he’s charming and slick and scams people. He’s sex-crazed, addicted to drugs and alcohol. But we cannot discount the fact that he did start out as a young professional with ambition and passion—something a lot of us can relate with.
Michael Scott, “The Office”
Some might say that he’s petty and a terrible judge of character but he also treats his employees like family and finds ways for them to succeed. He makes the office a fun place to be in, motivates people and connects with them on a personal level. Also, he’s not afraid to admit his mistakes.
Don Draper, “Mad Men”
While this self-absorbed boss is an advertising director who knows his stuff, he also ridicules his staff and is either sexually harassing or being rude to his assistant. He reminds us of that boss who cheats on his wife and thinks he can get away with it because he can buy everyone’s silence.
Natalie Figueroa, “Orange is the New Black”
She’s one of those who suck at their job but get paid way more than you do. She’s more concerned about the company’s public image than the welfare of those under her. She did embezzle huge sums of money to fund her husband’s political campaign at the expense of the inmates and their run-down facilities.
Miranda Bailey, “Grey’s Anatomy”
She has five rules and the intimidated interns have to memorize them. Her reputation as a tough boss precedes her but she’s also vulnerable, ambitious and hardworking. We live for one of those Miranda monologues on life, love, career and everything in between. S