A Look at Some of the Best Jokes About Bosses

Joel Anderson  |

Since the dawn of time, people have also been reacting to their bosses with the same semi-affectionate method for dealing with authority figures that they always have: humor. The ability to joke about the people you work for usually makes them and the job that much more bearable. So in that spirit, here’s a look at some of the best jokes about management we could find:

An employee is getting to know her new co-workers when the topic of her last job comes up.

“Why did you leave that job?” asks her co-worker. “It was something my boss said,” she replies.

“What did he say?” the co-worker queries.

“You’re fired,” she responds.

A young man is applying for a job. He comes in for the interview with his prospective boss.

“Do you smoke?” The manager asked.

“Never,” said the applicant.

“How about alcohol? Do you drink?” Asked the manager.

“No,” the applicant replied. “I’ve never had a sip.”

The boss smiles, pleased with the answer. “What about staying out late? Do you like to party?”

“No,” replies the applicant. “In bed by ten every night.”

The boss smiles, astonished at his luck. “Well I have to tell you, you sound like the perfect candidate,” he says. “What would you say is your biggest weakness?”

“I’m a pathological liar,” the applicant says.

On a Roman warship long ago, a galley boss stood at the helm one morning and shouted to the assembled rowers, “Today I have good news! All of you are getting extra food tonight!”

The rowers erupted into cheers almost immediately. All except for one very old man seated in the back, who began moaning in horror. “Oh God, no, not again,” he said.

Puzzled, a newer rower next to him asked, “What are you upset about? We’re getting extra food!”

“Because,” the old man responds. “This only happens when the Captain’s nephew wants to water ski.”

An employee goes to her boss to ask for a raise after two years with the company. The boss looks at her and says, "Because of the fluctuations in your position's productive capacity as juxtaposed to industry standards, it would be monetarily injudicious to advocate an increment."

"I don't get it," she asks.

"That's right," the boss says.

A man is interviewing for a new position at an insurance company as an actuary. The interview is going extremely well as they near the end, and the manager asks him what his salary expectations are.

Feeling confident that he’s the leading candidate, the man offers, “$150,000 a year, but that would depend on the benefits package.”

The manager smiles, and responds, “Well, what would you say to five weeks paid vacation, full medical, dental, and vision, we’ll match your 401K contributions up to 10% of your salary, and a company car.”

Thinking he’s hit the jackpot, the man jumps up in excitement. “Holy crap!,” he exclaims. “Are you kidding?”

“Yes,” the manager responds. “But you started it.”

A company’s owner calls a meeting of all of the company’s employees to discuss the company’s record profits in the last year.

“We all worked very hard to make this happen,” the owner says. “That’s why I’m handing out checks to all of you for $10,000 so you can share in the rewards!”

Ecstatic, the employees all burst into cheers.

“And if you show me the same level of effort next year,” the owner continues, “I will sign them!”

A man in a suit walks into a café holding a bucket of cow manure. He sits at a table and orders a coffee. The waiter brings it to him and he drinks it. The moment he’s done, the man upends the bucket onto the table, pulls a gun out of his jacket, and empties the magazine into the manure, splattering it everywhere, destroying the table, and sending the rest of the café’s customers scattering in a panic.

The next day, the café is still cleaning up from what happened the day before when the man walks back in with another bucket of manure and sits down as if nothing had happened. The waiter hurries over to his table.

“I’ll have a coffee,” the man in the suit says.

“Oh no,” the waiter responds. “No chance after what you pulled yesterday. What makes you think you can pull a stunt like that?”

“I’m in training for upper management,” says the man. “You come in, drink coffee, shoot the shit, and then disappear for the rest of the day."

A professional crew team enters a prestigious international race and comes in second place, losing by just a foot. Noting the team’s success, they’re purchased by a prestigious corporate firm looking to take advantage of their success.

On day one of the new ownership, the upper management comes in a with a series of solutions that they believe will finally give the crew team the additional foot it needs. At the core of their suggestions is reconsidering having eight rowers with one person steering. With better management, the executives insist, they’ll be able to get better results.

The next year, the team enters with its new structure: one person steering, a regional performance manager to “empower the staff to meet their full potential,” two steering managers (one for left turns and the other for right turns), four vice presidents of boating operations, and then a single individual rowing.

When the crew came in last place, failing to even finish the race, upper management took action to correct the trend. The rower was immediately fired for poor performance and cited the primary reason for the failure to do what they had accomplished last year. The managers promoted the manager of left turn to the new senior VP of boating operations, sold off the oars to “streamline” boating operations, and then used that money to pay performance bonuses to senior executives.

A man calls his boss and tells him he’s got a splitting headache and a bad cold, so he’ll have to miss work. The boss, interested in making their performance figures for the quarter, pushes his employee to come in despite his condition.

“Here’s what I always do,” the boss says. “I head home and have my wife pour me a bath, the hottest I can stand. I get into the bath and have her gently wash me with a sponge while I sip on some tea. Once she finishes, I then take her to the bedroom and make love to her. After that, I feel like a million bucks!”

“Okay,” his employee says. “I’ll give it a shot.”

Just after lunch, the employee walks into work. The boss walks over to his desk, smiling smugly.

“I told you,” says the boss.

“You were so right,” the employee responds. “That worked like a charm. Oh, and you have a NICE house!”


A man enters a pet shop and notices that there are three monkeys on display, each with different colored fur. He goes to the pet shop’s owner and asks how much they cost.

“Well,” the owner responds, “That brown one on the left costs $1,000.”

“$1,000!” the man exclaims.

“Yeah,” says the owner. “He knows how to use a computer.”

“I see,” the man says. “What about that grey one in the middle.”

“$2,000,” the owner tells him. “Not only can that one use a computer, he can code in HTML.”

“My goodness,” the man says. “What about that white one on the right?”

“Well, that one’s $10,000,” the owner says.

“$10,000!” cries the man. “What does that monkey do that could justify that price?”

“Well, he doesn’t really seem to do anything,” the owner says. “But those other two keep calling him ‘boss’…”

Two employees are stuck working late for the third time in four days. Tired and sick of being at the office, one of the employees jumps up and says “I got it! I know how to get time off work”

The other employee watches as he stands on his desk, knocks out two ceiling tiles, hooks his legs over a pipe, and starts hanging upside down from the ceiling. The manager bursts in to see what the commotion is about and the employee hanging from the ceiling starts muttering “I’m a light bulb. I’m a light bulb.” Over and over again.

The manager watches him for a minute, then tells him to get down.

“You’ve clearly been worked too hard,” the manager says. “Why don’t you go home and get some rest.”

The employee gets down from the ceiling, gathers his things, and walks out. The other employee gets up and follows him out the door.

“Where do you think YOU’RE going?” the Manager asks.

“Home,” the employee responds. “I can’t work in the dark.”

The senior manager of a company calls his VP into his office.

“Have you been fooling around with Janice from accounting?” The boss asks.

“No sir,” the VP replies. “Absolutely not!”

“Good,” the manager says. “Then you fire her.”

Two friends from business school finally find a chance to get drinks together after not seeing for each other for five years.

“I heard you founded your own company,” the first friend says.

“It’s true,” says the second friend morosely, clearly under a lot of stress. “But it’s not a big deal, the company is very small.”

“Small? How many people work there?” the first friend asks.

"About half of them," the second friend responds.

A company hires a new CEO with the intent of shaking things up and repairing a culture the board feels has gotten too lax. On his first day, the CEO walks into the break room to finds all of his employees in there, slacking off, telling jokes, and eating pizza. Ready to make a big first impression, the CEO storms up to the closest person.

“You!” the CEO shouts in his face, aggressively. “How much do you make in a week?”

“Me?” the man says, confused. “$500.”

The CEO pulls out his wallet and removes five $100 bills and shoves them at the man.

“Here,” he says. “Take a week’s pay and get out of here. I never want to see you again.”

The man shrugs, takes the money, and exits. The CEO turns to the remaining employees.

“Okay,” he says. “Now who wants to tell me who that sorry excuse for a worker was?”

One of employees steps forward.

“He delivered the pizzas,” she says.

DISCLOSURE: The views and opinions expressed in this article are those of the authors, and do not necessarily represent the views of equities.com. Readers should not consider statements made by the author as formal recommendations and should consult their financial advisor before making any investment decisions. To read our full disclosure, please go to: http://www.equities.com/disclaimer.

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