A Trusted Friend in a Complicated World

25 of the Worst Bosses You Could Ever Work For

Updated: Jul. 21, 2021

We asked Rainn Wilson from The Office to help judge your worst boss stories. Whether you laugh in recognition or cringe in outrage, you'll just be glad it's not you.

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My boss likes to save pennies

How much? I caught him in the break room retrieving paper cups from the trash can and shoving them back into the dispenser next to the water cooler. He didn’t even bother wiping off the lipstick. —Barbara B., Maryland (On a more positive note, here are the nicest things CEOs have done for their employees.)

2 / 25

After I’d been working in a small marketing agency for two years, my boss called me into his office

He told me I was finally receiving a promotion and a raise. I was elated. But when I reminded him about it the next day, he reneged. I started to argue, but he cut me off. “You know better than to take me seriously in the afternoons,” he said. “I’m drunk every afternoon.” —Elizabeth B., Georgia (These are the clear signs you can’t trust your boss.)

3 / 25

While on the job, I was unpleasantly surprised by the early arrival of my monthly cycle

After unsuccessfully begging every woman I could for “logistical support,” I reluctantly approached my supervisor, Jerry, and, choosing my words carefully, stammered, “I…um…would like to request permission to go home. I am…having trouble with…a female issue that…I’m not able to successfully resolve.” Poor old Jerry said, “Sure, no problem. But tell me, which female?” —Glenda Herrin, El Paso, Texas (Don’t miss the funniest real excuses people used to get out of work.)

4 / 25

It was a typical hectic Friday afternoon at our law office

My boss, meanwhile, was hundreds of miles away at a luxury resort preparing for a meeting. In the midst of my insane day, I got an urgent call from him. “You have to phone the hotel right away. It’s important,” my boss said. “Ask them to send someone to the pool area immediately.” “What’s wrong?” I asked. “We haven’t seen a waiter in 20 minutes, and we need our drinks refreshed.” —Bonah Bachenheimer, Long Beach, California (Here’s what you should do if your boss is a psychopath.)

5 / 25

Once after work, my boss, a self-titled “email man,” sent me a text message instructing me to check my email

I rushed over to my computer and pulled up the important missive. It contained two words: “Call me.” —Martin Hoffmann, Pearland, Texas (Check out these smart ways to build trust with your boss.)

6 / 25

My boss was notoriously cheap, so when he handed me a birthday card, I was pleasantly surprised

“Thank you,” I said. “You’re welcome,” he replied. “And when you get through reading it, take it to Robin down the hall. It’s her birthday today too.” —Gail Snyder, Georgia

7 / 25

Our former department head was famous for his malaprops

Here are his greatest hits: “The Greek pyramids weren’t built in a day.” “Spurt me out an e-mail.” “Let’s not put the horse before the cart.” “Tonight we’re eating at the Tibetian restaurant.” “It’s not rocket surgery.” “It’s all smoke and windows.” “Nothing is nailed in stone.” “Sometimes you have to roll the dice, and it comes up tails.” —Steve Wehmoff, New York

8 / 25

I was five and a half months pregnant, and the principal decided it was time we had a chat about dress code

My dress code. “I don’t know if you are aware, but your body is changing,” she said awkwardly. “I’m concerned because your breasts have become inappropriately large for a secondary school teacher.” Long, uncomfortable pause. “That’s all,” she said, dismissing me. She never did say what she expected me to do about the problem. —Kristen J., Tennessee (Here are more subtle things bosses notice about their employees.)

9 / 25

I stayed late with my boss fielding customer queries

But after one call, a look of horror crossed his face. “I have to get out of here!” he yelled. “That was my girlfriend. Her husband is in a motorcycle gang, and he just found out about me. He’s on his way over here right now!” The husband had never laid eyes on him, he said, but knew he worked late nights at the newspaper. My boss then left me with these words: “Keep answering phone calls from customers!” And out the door he went. Being eager to please, I stayed put. But then it hit me: My boss was setting me up. He was hoping I’d be mistaken for the boyfriend! I quickly grabbed my coat, turned out the lights, and got out of there. —Phil P., Pennsylvania

10 / 25

At my old office, one of the bosses went crazy and threw his computer out the window, 50 floors above street level

It bounced on a ledge a few stories down and stayed there, thankfully. Later, he was taken out of the office in a straitjacket. Oddly, he returned to work a month later. —B. O., Montclair, New Jersey

11 / 25

Shortly after 9/11, our division manager wanted to do something to unite the company

He told my boss to assemble everyone in the boardroom and to place the lyrics of the national anthem on each seat. On the day of the event, I had filled the room with streamers, balloons, and small flags and, as requested, had placed a song sheet with the lyrics of the national anthem on each chair. “What’s this?!” the division manager shouted at me. Pointing to the song sheet with the title “Star-Spangled Banner” on it, he continued, “I wanted the lyrics to the national anthem!”—Anonymous

12 / 25

My boss’s assistant, an efficient middle-aged woman, spent much of the morning transcribing a letter he had dictated

She suddenly let go with a string of expletives, words I’d never realized were in her vocabulary. “Is everything all right?” I asked. Steaming, she rewound her digital dictation device a few seconds and let me listen to what she had heard: my boss saying, “No, no, forget all of that. [Pause] ‘Dear sir …’” —Johnny Walker, Kempton, Pennsylvania (Make sure you know the things you should never say to your boss.)

13 / 25

I was working as a reporter for an “alternative” New York City newspaper

Our office was a storefront with a double door. The publisher owned a small Honda, a tiny 1970s model no bigger than a shopping cart. Or so it seemed, until he decided to park it in the office at night to avoid the hassle of parking on the street. “It will never fit,” we told him. “Sure it will,” he said. So we pushed all the desks against the wall, and he backed the vehicle across the sidewalk. Sure enough, the rear end of the car made it through the door with an inch to spare on either side. Wow! This was actually going to work! We were going to park a car in the middle of our office! Alas, no. Half an hour later, and dizzy from breathing carbon monoxide, he could not squeeze the side mirrors through the doors. The strange thing is, as we moved our desks back, I was as disappointed as my boss that his scheme didn’t work. —D. N., Morristown, New Jersey

14 / 25

After I worked through lunch to help my boss with a report, he offered to show his appreciation by taking me out for a bite

The place he had in mind had a wonderful buffet, he said, with foods from around the world. I was absolutely salivating with each detail. So what was his idea of an exotic dining establishment? Sam’s Club. We spent the hour dining on the free samples they handed out. —Wendy Brown, Illinois

15 / 25

I’d gone on vacation without having processed a pay raise for one of the employees of our medical practice

When I returned, I discovered that my boss had filed the forms away. I opened the file cabinet and looked up the employee’s last name, first name, subject matter—nothing. “Hey, where did you file those papers?” I asked my boss. “Look under M,” he said. “M?” I asked. “But his initials are C. S. Why would you file it under M?” Exasperated, he said, “For money.” —Deborah Bush, Virginia

16 / 25

My boss’s biggest nemesis is the English language

During one meeting, I asked about the status of a particular report. He replied, “We aren’t going to prepare that report. It would be an exercise in fertility.” It would be funnier if he didn’t earn four times more than I do. —Sue T., Ohio

17 / 25

The front office asked us to figure out the square footage dedicated to each department in our clothing store

To save time, I suggested we count the ceiling tiles above each department. “They’re each two square feet. Counting the tiles would give us an accurate dimension of each department without having to work around all the displays,” I explained. My boss hated the idea. “He-lloo,” she said, sarcastically, “we need the square footage of the floor, not the ceiling.” —Terri Hanke, Kansas

18 / 25

As a teenager, I worked at a diner that had an all-glass front

One day, a blizzard blew in, knocking the wind chill factor down to 40 below. But my boss sent me outside anyway to wash the windows. “Put some alcohol in that bucket so the water doesn’t freeze,” he said. “The water? What about me?” I asked. He grunted, “You’re too young for alcohol.” —Scott Donovan, Charlton, Massachusetts

19 / 25

On my first day at a new job, I arrived to find someone in the office that I’d been told would be mine

Puzzled, I went to find the person who had hired me, but she was away at a conference. So I told another person my story. She made a few calls, then told me to find a place to sit. “Don’t speak to anyone,” she ordered me. “Just wait for someone to find you something to do until your boss returns.” Turns out, before my boss left town, she had forgotten to fire the person I was replacing. —Nancy E., Massachusetts

20 / 25

My boss was a real gentleman

Although it wasn’t my job, he once made me mow the lawn around our office building. I was wearing a dress and high heels. —Tamara T., Nebraska

21 / 25
iStock/Izabela Habur

During a faculty meeting at our school, our principal grew frustrated with the lack of attention he felt was his due

Raising his voice, he shouted, “Listen, people. Communication is a two-way street. When I talk, you have to listen.” —T. D., via Internet (Don’t miss these signs your boss is a micromanager.)

22 / 25

My (former) boss had a surprise for me one day

“I brought in muffins,” he said. “They’re in the break room. Help yourself.” Of course, I ran to get my fill. But when I got there, I found all the muffins were topless—only the stumps were left. “What gives?” I asked him. “Oh, yeah,” he said. “I only like the muffin tops.” —Carl Graf, Tewksbury, Massachusetts

23 / 25

As an employee representative, it was my unfortunate duty to do battle with our boss whenever he asked too much of his employees

“You think you know everything, don’t you?” he yelled at me once. “No, sir, I don’t,” I countered. “But I do know what the law says. And the law says—” “The law!?” he roared. “The law has absolutely nothing to do with what goes on in this company!” —Y. F., Bellevue, Washington

24 / 25
istock/Henk Badenhorst

I was performing with another comic, and part of our deal was a free meal.

After my set, I asked our waitress if I could get a bite. She said no, so I asked to speak with the manager. Next thing I knew, he was charging straight at me, screaming that I was rude to his waitress. He chased me around the table, yelling and lunging at me. Thankfully, the bouncer separated us. When the other comic got offstage, I said, “You won’t believe this, but the manager tried to kill me!” “Really?” he said. “I didn’t think your set was that bad.” —D. F. Sweedler, New York, New York

25 / 25

During my brother-in-law’s first performance review…

…His boss said, “I’m not quite sure what it is you do here. But, whatever it is, could you do it faster?” —Jeanie Waara, Philip, South Dakota (Check out the secrets your boss won’t tell you—but you need to know.)