The Worst Bosses Of All Time (PHOTOS)

Most of us have experienced the dumb boss, the arrogant boss, the mean boss. But, as the accompanying collection of famous business tyrants illustrates, it takes a certain special something to rank as one of the worst bosses of all time.

Specifically, we're thinking of bosses who coerce you into into doing their yard work, bosses who throw phones at you, or those who (reportedly) try to make you kiss a coworker. The stories of legendary despots like Vogue's Anna Wintour or the cantankerous billionaire Sam Zell are so widely known, they've almost become acceptable. (Well, not quite.)

Take a look at the soul-crushing antics of some of the most notorious employers in our slideshow of malicious bosses. But, if you've got horror stories of your own, we're all ears! Email us with your worst examples of how a boss has treated you, flown off the handle or otherwise made your life a living hell. Send your stories to HuffPost-At-Gmail-Dot-Com -- we'll be building a list of your most awful anecdotes.

	1 / 9		Anna Wintour When there is a bestselling novel and movie about your cruel behavior in the work place, that can only mean one thing: you're a legendary work despot.  While Wintour’s inclement personality is certainly fitting for the industry in which she works, employees are reminded not to look her in the eye for fear of her wrath.

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Comments

[trintod]

We need less sensationalism and more reporting about the problems real people face on a day by day basis. There's a lot of angry & scared people who have lost jobs, house, and sanity.

good articles; http://ow.ly/dmzm

Need more change from Obama

[Leper]

Anna Wintour? Really? You know, there is a difference between a boss who is demanding and a boss who is completely out to lunch... like Marge Schott.

[Leper]

I would have replaced Scott Rudin with Jon Peters. Yes, Scott Rudin can be extremely demanding, but his former assistants have gone on to successful careers and Mr. Rudin has given references.

Jon Peters, on the other hand, fired a guy because his wife wouldn't get an abortion, which was demanded by Peters. That ain't pro-choice, either.

[JScott]

And Jon Peters ONLY 'got in' because he was Barbra's hairstylist.

[rhubardpi]

I expected to see my ex-wife on here. Also Mary Durgin who once was my boss at the IRS. she was one of only 2 bosses I have had, in some 50 jobs over 47 years, who ever lied to my face. She was one dried up prune of an IRS executive.

[LMPE]

If you have a work ethic, then expect this!

[wietog]

Maybe there's a connection between those who have the arrogance to be leaders and their pathological behavior?

I think our animal side really comes out in extreme examples such as these. The very qualities that help us succeed, in excess or extreme measure, can destroy us.

[brooklyncitizen]

Doesn't look like they are being destroyed...unless making tons of money is destructive.

[Erdgeist]

For the real truth behind the bosses, and for that matter, many of those in power, read Dr. Robert Hare's book, _Snakes in Suits_. It is about psychopathy in corporate America (Dr. Hare is one of the world's leading experts on psychopathy).

Here is Dr. Hare's site: http://www.hare.org/

[schatsie]

Great link! wonderful food for thought. Now read Free Lunch and tell me who should not go to jail for RICO....

[Punkynsnow]

Where is George Steinbrenner on this list? I've known people who worked for him and he was totally out there. Also, Col Allen of the NY Post is another one who should make this list.

[Safire]

I call them sadists!

[platanoman]

What about Leona Hemsley? She's not on the list?

[JScott]

Karma....she went to prison then I think died estranged from her family.

[LeroyJenkins]

my 3 yr old says "i'm the boss" like Tony Soprano

i lov him!

[Ralph Noyes]

This lightened up my day.

I know I can be a demanding boss on occasion, but I make up for it most of the time by being brilliant, productive, and charming.

My staff has only walked out on me once -- 20 years ago, for two hours. Lunch, really, but they claimed it was a walkout.

Not every demanding boss is a bad boss. Not every easygoing boss is a good boss.

Employees are entitled to be treated well.

Employees who expect their boss to suffer fools gladly tend not to survive, nor are they entitled to an expectation of surviving.

[Furby2]

And you consider this a badge of honor?

[getoffmedz]

Ralph, what are you doing these days?

[Ralph Noyes]

Running a successful law firm -- with long-time employees.

Still friends with the ones from 20 years ago. I moved 700 miles, they didn't, but I'd hire them back and they'd return. We had a lot of fun as well as the occasional gnashing of teeth.

My little critics here don't sound like the kind of people I would hire, or those who would last long if I did.

[bltmn]

The best boss I ever had was also the most demanding, tyrannical, belligerent SOB on the planet. But you always knew, in no uncertain terms, what was expected and where you stood. And believe me - things got done.

The worst boss I ever had was charming, personable, and eventually stabbed me square in the back. He showered me with praise while secretly undermining everything I did.

Sexual harassment, criminal activity, and physical violence are always unacceptable. But don't confuse toughness with malice, or sweetness with benevolence.

[Furby2]

The best boss I ever had knew how to balance high expectations and fairness. You would never see him behave abusively but he still commanded respect. Good leaders don't lead by fear but by example.

[RevBookburn]

J. Edgar Hoover had to be a hoot. If one saw him with Clyde Tollson in their dresses, they would have had to keep the same facial expressions and refrain from laughing out loud.

[HamletsMill]

Anna Wintour. A Lemon Maragne pie. Me. Force.