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  • Writer's pictureJace Shoemaker-Galloway

National Boss Day: Best badass bosses we love to hate

Today is dedicated to the men and women across the nation who sign our paychecks. It's National Boss Day, also referred to as Bosses Day and/or Boss's Day.

This annual "holiday" was created in 1958 by State Farm secretary, Patricia Bays Haroski. She created the day in an effort to show appreciation for bosses and improve the working relationship between employer and employee. National Boss Day is observed on Oct. 16 unless the day happens to fall on a weekend, then it is celebrated on the working day closest to the 16th.

Let's be frank. Most of us have had to deal with bosses at some point in our lives. While many bosses are supportive, fair and understanding, other employers can make life at work just plain miserable! Whether you are fond of your boss or, well, not so much, having a job in today’s economy is reason enough to celebrate despite what kind of boss you have!

While working in a hostile work environment is no laughing matter, check out a few of the baddest fictional and real-life bosses on the planet!

Best Badass Bosses We Love to Hate

  • Nine to Five - Dabney Coleman doesn't stand a chance in this 1980 comedy starring Jane Fonda, Dolly Parton and Lily Tomlin.

  • Private Benjamin - Sheltered Judy Benjamin (Goldie Hawn) gets a rude awakening from Capt. Lewis (Eileen Brennan) in this fun 1980 film.

  • The Office - Love him or hate him, Michael Scott is truly one of a kind!

  • The Devil Wears Prada - Yes she does! Miranda Priestly (Merly Streep) is as tough as they come when it comes to bosses.

  • Star Wars - Does the name Darth Vader ring a bell?

  • Wall Street - Two words - Gordon Gekko.

  • Disclosure - Michael Douglas and Demi Moore star in this 1994 drama.

  • The Proposal - Margaret Tate (Sandra Bullock) has quite the proposition for her handsome assistant (Ryan Reynolds.)

  • Horrible Bosses - Speaking of horrible bosses, Jason Bateman, Charlie Day and Jason Sudeikis all have one.

  • Working Girl - Bad boss Sigourney Weaver and secretary Melanie Griffith star in this 1998 film co-starring a young Harrison Ford.

  • Bridget Jones's Diary - Thoughtless boss Hugh Grant and Renee Zellwegger star in this popular 2001 film.

  • 101 Dalmatians - With a name like Cruella De Vil, she's got to be mean!

  • A Christmas Carol - Ebenezer Scrooge is the ultimate scrooge!

  • It's a Wonderful Life - This classic 1946 holiday film stars James Stewart, Donna Reed and Lionel Barrymore as the crotchety Mr. Potter.

  • Leona Helmsley - Known as the "Queen of Mean," real-life hotel heiress Leona Helmsley was eventually convicted of fraud and tax evasion. She left a chunk of change, $12 million to be exact, to her beloved pampered pooch, Trouble.

  • J. Edgar Hoover - If you think your boss is a little paranoid, at least you haven't been accused of being a communist!

  • Bernie Madoff - This "successful" entrepreneur made his gazillions by scamming clients and was eventually sentenced to 150 years in prison for a variety of crimes.


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