It’s a sunny morning, and you arrive at work with a smile on your face. You have a good job, great colleagues, and the company culture is pretty fine. But then you get to your desk, start getting through your e-mails, and your face twists. You realize that your boss has left you to take care of another one or two of those long, annoying, and trivial tasks that would be insignificant even for an intern on their first day. If only they would let up for a minute! But instead of doing that, they keep piling on the pressure until you eventually break down. There is nothing worse than being stuck working for someone that you can’t stand. And if that someone is impossible to please and unreasonable, then it can make life at work very difficult despite all the other good things.
But don’t despair yet! We have collected some of the best boss jokes that are sure to help lighten the mood around the office. These jokes about the boss are sure to lift everyone’s spirit and make you burst out laughing! And if, instead of a horrible boss, you actually have a great director who knows how to take a joke, why don’t you share these ones with them too?
(Disclaimer – We don’t take responsibility if you get fired.)
#1 Boss Doesn’t Get It
At my boss’s funeral kneeling and whispering at the coffin. “Who’s thinking outside the box now Gary?”
#2 Guess I aimed a bit too high
They say dress for the job you want, not the job you have. My boss still didn’t think a spacesuit was “Appropriate work attire.”
#3 Midweek Mood: Relatable and Real
Boss: “This is the third time you’ve been late to work this week. Do you know what that means?”
Me: “It’s Wednesday?”
#4 Power Move: Silence is Loud
My boss told me I intimidate my coworkers, so I just stared at him until he apologized.
#5 Team spirit: questionably distributed
“And remember,” said the boss, “There’s no I in TEAM!”
“Yeah,” muttered one of the peons, “And there’s not much sign of U in it either.”
#6 Blessed with Brutal Honesty
I asked my boss if I can come to work a little late today. He said “Dream on.” I think that was really nice of him.
#7 When “Corona” Means Just a Drink
Boss: “You called in sick yesterday and said you had the Coronavirus. You can’t be here until you get tested.”
Me: “I said I had a case of Corona and I wasn’t coming in to work. I never said anything about a virus.”
#8 Worth the wait, low key
Someone once asked me if I would shoot my boss for $50,000… I said yes, I would definitely do that, but it’s going to take me a while to come up with $50,000.
#9 Taking Boss Advice Literally
My boss told me to have a good day. So I went home.
#10 Powered off but not forgotten
My boss calls me “The computer.” Not because of my calculation skills but because I go to sleep when left unattended for 15 minutes.
#11 Weekend Mode: Immune System on Vacation
Boss: “How is it that you are always sick on weekdays?”
Me: “It’s my weekend immune system.”
#12 Hiring The Anti-Hire Expert
Boss: “Why should we hire you as an reverse psychologist?”
Me: “You shouldn’t.”
#13 Not the kind of opportunity I wanted
Man says to his boss, “Can we talk? I have a problem.”
Boss: “Problem? No such thing, we call it an opportunity!”
Man: “Ok, I have a serious drinking opportunity.”
#14 Brewed Trouble, No Filter
I got fired from my job at the coffee factory. My boss said it was because I had no filter.
#15 Quietly conquering without the chaos
How do you make people think you’re the boss?
Stand around and do nothing.
#16 Subtle flex level: expert
I told my boss that I wanted an increase in my paycheck. My next one had a larger font.
#17 Workplace entertainment, unexpected edition
I wonder what your boss has in common with a slinky. Both of them are entertaining to watch fall down the stairs.
#18 This is why he’s irreplaceable
The Boss always insisted that only Abdul should serve his coffee, but yesterday, this conversation happened.
Boss: “Abdul, since the last 8 years you have brought me coffee filled to the brim without spilling even a drop. How do you manage that over these stairs?”
Abdul: “Sir, just before I climb up the stairs, I take a big sip. As I get upstairs, I put it back.”
Today is Abdul’s farewell party.
#19 Too wild to handle
I miss the times when I was working at the zoo. My boss fired me just because I left the lion’s gate open. I mean who would steal a lion?
#20 Sarcasm: 100% Effective, Apparently
Boss: “Sarcasm will get you nowhere in life!”
Me: “Well It got me to the ‘International Sarcasm’ finals in Santiago 2011.”
Boss: “Really?”
Me: “No.”
#21 Pour Decisions Lead to Beer Cheers
“My boss is goin through a divorce an I fell really bad but it’s kinda awesome bc now he always buys the beer.”
Image source: CodyWilliamson7
#22 Next-level flex, low-key bizarre
My boss is so rich he even bought a kid for his dog to play with.
#23 That escalated quickly
My boss said he races boats. So I said, “Wow, you must be a fast swimmer!”
#24 CEO of the Moo-niverse
What do you call the boss at Old McDonald’s Farm ?
The CIEIO.
#25 When paying gets you hired
A guy got an Interview for a job with EA:
Boss: “The second part of your resume is missing.”
Applicant: “For the second part you have to pay 20$.”
Boss: “Welcome on board.”
#26 Meet Your New Stress Job
Got some bubble wrap delivered to work yesterday.
The boss said, “Pop it in the corner.”
Took me five hours!
#27 Same Pay, Different Paperwork
Boss makes a dollar, I make a dime. It’s just another day at the United States Bureau of Engraving and Printing.
#28 Freedom Comes With Backseat Drivers
I was in a taxi when the driver said: “I love my job. I am my own boss, nobody tells me what to do.” I then told him to turn right.
#29 Adulting Perks Nobody Warned Me About
I told my boss that he needs to raise my salary because two companies are after me.
Boss: “What companies are those?”
Me: “The electricity company and the water company.”
#30 Well, that escalated quickly
Told my boss he needs winter tires. Got fired. Apparently that’s something offensive to say to people in wheelchairs.
#31 Well, at Least I Tried
I waved at my boss as I left the office. It seems he wasn’t impressed maybe next time I’ll use all my fingers.
#32 Well, that escalated quickly
“I like talking about team building right after firing 25% of my staff.”
Image source: MyBossIsSatan
#33 Empty desk, empty excuses
I remember my boss once pointed to my desk which was a mess… He said that a cluttered desk is a sign of a cluttered mind. He wasn’t too happy when I pointed out that his desk was empty.
#34 Well, That Escalated Quickly
I gave up my seat on the bus to a blind guy and my boss fired me for it. Guess I’ll have to find a bus driving job in a new city.
#35 Well, That Escalated Quickly
I walked into work and my boss handed me a brochure on anger management. I just lost it.
#36 When your job literally sucks the air out of you
After an altercation with my boss, I decided to leave my job at the helium factory. I refuse to be spoken to in that tone of voice.
#37 Zero Urgency
A guy shows up late for work.
The boss yells: “You should have been here at 8:30!”
He replies: “Why? What happened at 8:30?”
#38 Wait, So I’m Still Employed?
I got fired from the unemployment office on Friday. My boss said, “Clean out your desk, and I’ll see you in the office on Monday.”
#39 Not The Fuse I Wanted To Blow
My boss wanted me to put some new fuses in a car. I refused.
#40 Found the joke in your budget meeting
My boss asked me to start my presentation with humor. So, I put my paycheck on the first slide.
#41 When Your Brain Hits Pause
Boss: “Got it?”
Me: “Got it.”
Brain: “Got what.”
Image source: PleaseBeGneiss
#42 Guess I’m just here for the car fund
My boss arrived at work in a brand new Lamborghini. I said “Wow that’s an amazing car.”
“If you work hard, put all your hours in, and strive for excellence, I’ll get another one next year.”
#43 Hammers Don’t Need Lab Rats
A boss and his employee are discussing the testing of their products:
Employee : “We have got to stop testing our products on animals.”
Boss : “Oh yeah ? Other companies do it all the time , so why shouldn’t we ?”
Employee : “Yeah that’s good and all but we make hammers.”
#44 Weekend plans: fashionably late, as always
Boss: “Can you work this weekend?”
Me: “Yeah no worries but I’ll probably be a bit late as public transport is slow on weekends.”
Boss: “What time will you get here?”
Me: “Monday.”
#45 Perfect excuse level: Expert
Boss: “You’ve got to find a way to make fewer mistakes on the job.”
Worker: “Ok, how about I come in later in the morning?”
#46 That’ll teach me to be too hands-on
I got fired from my job as a massage therapist. My boss said I rubbed people the wrong way.
#47 When nerves turn into job offers
Boss: “Why do you-”
Me: “*sshhh*”
Boss: “What is your biggest wea-”
Me: “*sshhh*”
Boss: “(whispering) you’re hired. Welcome to the library.”
#48 Classic boss energy right there
My boss called me and said, “Why didn’t you call me back when you said you would 3 hours ago?!”
I told him, “When did I say that…? I don’t recall…”
#49 Brick by brick, chaos incoming
Boss, I left a huge masonry order on your desk. When you see it, you’ll ship bricks.
#50 Living the Punchline Life
I told my boss that I’m quitting my job to become a comedian.
He said, “You can’t be serious.”
I said, “I know.”
#51 Classic excuse level: expert
Me: “Boss, I’m sorry I am late. I was having computer issues.”
Boss: “Hard drive?”
Me: “No, the commute was fine. It was my computer.”
#52 Pun intended, nailed it
Boss: “How good are you at PowerPoint?”
Me: “I Excel at it.”
Boss: “Was that a Microsoft Office pun?”
Me: “Word.”
#53 Math roast? Ouch, boss!
My boss said my math skills are average. That’s just mean.
#54 Plot twist with zero chill
My coworker said to me, “If the boss doesn’t take back what he said to me, I’m leaving the company.”
I asked, “What did he say?”
“Leave the company.”
#55 Quitting Felt Better Anyway
My boss accused me of stealing, and fired me from my job at the furniture store. But I regret nothing, sometimes you have to take a stand.
#56 Math Skills Not Included
Me: “Can I leave work early?”
Boss: “Only if you make up the time.”
Me: “Ok, 45 past 60.”
#57 Lame Excuses Win Sometimes
I called my boss this morning.
“I won’t be coming in today,” I said. “My legs aren’t working properly.”
“What kind of excuse is that?” He asked.
I replied, “A lame excuse.”
#58 Clueless And Unbothered
Told my boss I would leave my job because they weren’t giving me sufficient training.
“Well, you know where the door is,” he said.
I said, “Actually no, I don’t.”
#59 Guess I’m a crystal ball now
My new boss told me that he expects me to be on call 24/7. But I don’t really mind as the 24th of July is ages away.
#60 When Your Boss Thinks You’re Extra Well-Done
At the office barbecue, I grilled a medium rare steak and my boss said, “I like it well done!” I said, “Thanks. That means a lot to me.”
#61 Pressure? I’ll just sing instead
My new boss asked if I could perform under pressure. I said, “No, but I can do a great Bohemian Rhapsody”
#62 When Your Boss Actually Means It
The cop wanted to retire from his job as a traffic officer. His boss gave him the green light.
#63 Guess Who’s Watching Your Windows
I work for a window cleaning firm. My boss often does spot checks.
#64 Silent savage energy
What’s the best way to criticize your boss?
Do it quietly so they can’t hear you.
#65 Wait, You Heard That Too?
I heard my boss say I was worth paying attention to. He was telling a security guard.
#66 Me pretending that was funny
If your boss cracks a joke at your expense and you laugh “ahahahahagivemaraisehahaha.“
#67 We’re Already In The Meeting
Boss: “Can I see you in my office?”
Me: “Well, you can see me right now, I’m sitting next to you while you email me.”
Image source: jennyjrubin
#68 Sheep Takes No Crap
“I love my job!” exclaimed the farmer.
“All you do is boss me around all day!” complained one of his sheep.
“What did you say?” challenged the farmer.
The sheep glared back and growled… “You herd me.”
#69 Luck’s a Filter Now, Apparently
With a pile of 300 resumes on his desk and a need to pick someone quickly, my boss told me to make calls on 50 and toss the rest.
“Throw away 250 resumes?” I asked, shocked. “What if the best candidates are in there?”
He thought for a moment and said, “You have a point but then again, I don’t need people with bad luck around here.”
#70 When the mentor club hits different
My boss pulled me into his office. He sighed and said, “Look…when it comes to drinking on the job, I haven’t got much tolerance.”
“That’s okay,” I replied, “I was a rookie once too.”
#71 When Your Paycheck Is Literal Veggies
I quit my job after my boss started paying me in vegetables. I couldn’t live off of that celery.
#72 At Least I’m Consistent
My boss said to me, “You’re the worst train driver ever. How many have you derailed this year?”
I said, “I’m not sure; it’s hard to keep track.”
#73 When the boss pops off, you rise up
Got promoted at the bakery after my overweight boss died. I’ve got some big chouxs to fill.
#74 Posture check: Nervous already
My boss is going to fire the employee with the worst posture. I have a hunch, it’s going to be me.
#75 Plot twist: I’m undercover
My boss: “You’re fired.”
Me: “*Turns in gun and badge*”
My boss: “You’re a waiter, where did you get those.”
#76 This Boss-Employee Banter Is Peak 2024
An employee asks his boss, “Can I have two weeks off for Christmas?”
His boss replied, “It’s May…”
To which the employee responded, “Oh, sorry. May I have two weeks off for Christmas?”
#77 Boss energy: 100% lost already
My boss came to me at lunch:
“Where the hell have you been? I’ve been trying to find you all morning!”
I shrugged and said, “Good employees are hard to find!”
#78 Plot twist: He’s the boss now
A man receives a call at work:
His boss asks him, “Who was that?”
“Just some random guy.”
“Call him back NOW!”
The man calls back and says, “911, what’s your emergency?”
#79 Unleashing Keyboard Kung Fu
John is being shown around the office by his new boss. They enter the IT department and John sees a man using two keyboards at once. “That’s incredible”, says John. “Trust a geek to use two keyboards at once”. “Hey!” replied his boss. “That’s stereotyping.”
#80 Peak workplace vibes
A boss is like a seagull. He flies in and makes a lot of noise. He drools all over everything.
#81 Spreadsheet game: gold medalist energy
My boss asked me how good I am at making spreadsheets. I told him “I Excel at it.”
#82 Rock solid excuse, honestly
“What did the geologist say to his boss?”
“I don’t know.”
“Please don’t take me for granite.”
#83 Plot twist: Security or binge-watching champ?
As a security guard, my Boss said my job is to watch the office. I’m on season 6 so far, and not sure what this has to do with security.
#84 Leapfrogging for the paycheck
My boss said he’d give me a bonus if I did an impression of a frog. I jumped at the opportunity.
#85 Well played, boss.
My boss said I was going to see a big increase on my Payslip this month… He increased the font size.
#86 Bold move, now we’re talking
My boss was giving a presentation and no one was asking questions.
So my boss says: “The person who asks the first question will get a raise, the second will get a promotion, and the third will get a million dollar.”
So I raised my hand and said “I have three questions.”
#87 Well, this escalated faster than expected
I caught two teenagers smoking pot outside my office window. Fifteen minutes later my boss caught me and two teenagers smoking pot outside my office window.
#88 Put Your Foot Down, Literally
I don’t mind following rules at work, but when my boss told me to stop impersonating flamingos… I had to put my foot down.
#89 Mission accomplished, I guess
I gave my boss some maracas for Christmas. He kept talking about how he wants to shake things up.
#90 Facial Hair? Not in This Office
My boss doesn’t tolerate any beards or mustaches. He’s a real shave driver.
#91 Guess Who’s the Walking Wall Now?
The decorator got wallpaper on himself instead of the wall. His boss tore a strip off him.
#92 Talk About All the Right Angles
What did the computer programmer talk to his boss about?
Arrays.
#93 Boss level: Expert, Employee level: Struggle
What’s the definition of a power struggle?
Your boss has the power, and you have the struggle.
#94 Friday 4 PM: The Silent Agreement Hour
The boss always scheduled a management meeting at 4:00 pm on Friday afternoons. When an employee asked him why, he replied, “I’ve found that late Friday afternoon is the only time when no one wants to argue with me.”
#95 Retirement Plans, Not Marathons
I was told by my boss that I have to set up the company’s 401k. However, I do not think I can run that far.
#96 When Work Meetings Turn Stand-Up Comedy
My boss sent me an email:
Boss: “Send me a joke!”
Me: “I’m working right now!”
Boss: “That was great! Send me another one!”
#97 Plot Twist: Swimming to Work Now?
John : “Hi boss it is raining heavily today so I would not be coming.”
Boss: “You stated in your job application that swimming was it hobby so see u at at 11am.”
#98 When You Go Full McOverboard
Me: “Welcome to McDonalds, can I take your McOrder?”
McDonalds Boss: “Again *rubs temples* you don’t need to put Mc in front of words.”
Me: “Oh ok *turns back to customer* welcome to Donalds.”
Image source: ArfMeasures
#99 Well, This Is Awkward
[My funeral]
Boss: “*solemnly placing his hand on my casket and sobbing* How could you do this to me we are so understaffed today.”
Image source: rob_thegeek
#100 Dead serious about deadlines
My boss: [whispering into my coffin] “You haven’t submitted your timesheet.”
Image source: KeetPotato
#101 That Pun Hit Different
I asked my boss if we would ever hire felons to run pipe. He said no, they won’t let a conduit.
#102 When Life Deals You No Cards
My first day at the casino I was late for work, my boss yelled at me, and they put me at a Blackjack table with no cards. I looked at all the players and said “I can’t deal with this. “
#103 Plot Twist: I’m Still Here
I’m not going back to work until my boss takes back what he said… “You’re fired.”
#104 The art of the strategic sick day
I called work this morning and whispered, “Sorry boss, I can’t come in today. I have a wee cough.”
He exclaimed, “You have a wee cough!?”
I said, “Really?! Thanks boss, see you next week!”
#105 Rounding Up the Sheep, Literally
At the end of the day, a border collie reported back to the grazier, “All fifty sheep accounted for, boss!”
“Wait, I only have 48 sheep!” he replied.
“I know,” said the dog, “but I rounded them up.”
#106 Bossing myself feels weirdly awesome
I quit my job to start a cloning business and it’s been great, I love being my own boss.
#107 Well, that joke didn’t land—guess I’m Korean for the door
My boss fired me for making too many Asian jokes, it was the end of my Korea.
#108 Chewed Out, Literally
Did you hear about the guy who fell in a vat of gum at the bubblegum factory?
His boss chewed him out.
#109 Work’s just crushing my spirit
What did the can crusher tell their boss?
I quit. This is soda-pressing.
#110 Classic “I’ll show you” energy
My boss says I have a preoccupation with vengeance. We’ll see about that.
#111 Best excuse for a sweet exit
What did the doughnut maker say to their boss?
“I quit because I’m tired of the hole business.”
#112 Classic “Oops, Already Booked” Energy
Unfortunately, my boss said no to my time off request. However, the flight is booked. So I hope she comes up with something.
#113 Boss energy: truth bombs and stink bombs
So we were working with a new client at work and my boss farts, he said “A little gas never killed anyone.”
#114 Plot twist: Hands-free hustle
A man with no arms is tasked with a lot of jobs then he says to his boss “I can’t handle all of this.”
#115 Ah yes, virus bedtime rules
“My boyfriend’s boss is scared of getting the coronavirus so naturally she has decided that instead of finishing at 5:30 they will finish at 4:30, because as we all know the coronavirus only comes out after 5.”
Image source: iya_lucy
#116 Mood swings meet medical drama
“My boss just came in my office and cried because she felt bad for snapping at me today. I work at a hospital how hard is it to get her xans?”
Image source: tayloryvette528
#117 Guess It’s Time to Aim Elsewhere
The human cannonball retires. After a long career of being blasted into a net, the human cannonball was tired. He told the circus owner he was going to retire. “But you can’t!” protested the boss. “Where am I going to find another man of your caliber?”
#118 Extra can, extra chaos
So, today my boss asked me to pick up 6 cans of Sprite for a meeting. However, when I returned, I realized that I had picked 7 up instead.
#119 Plot twist: patience pays off?
A boss tells a blonde applicant, “I’ll give you $8 an hour, starting today, and in three months I’ll raise it to $10 an hour. So, when would you like to start?”
Blonde: “In three months.”
#120 Boss Level: Expert Mode Activated
What are the best ways to be a good boss?
If you’re in charge, ponder. If you’re in doubt, mumble. If you’re in trouble, delegate.
#121 Office drama hits different
A man walks into the bar…
The bartender: “Hi Dave!”
The boss faints.
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