'My boss put candles in his dishwasher': 30+ Goofy bosses who make their workplace feel like 'The Office'

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Jun 10, 2023 3:00 PM EDT

Having a funny boss is amazing, but having a wanna-be funny boss is much less ideal. 

You'll have many types of bosses throughout your life, and one specific type is the "Michael Scott" from The Office type of dude. This person is a manager who loves attention, thinks they're the ultimate people person, and most importantly, think they know everything about running their business. When u/Multicalibrador asked r/AskReddit, "What's the most Michael Scott-ish thing your boss ever did?" people had some excellent answers to the question. 

The bosses below do have their similarities to The Office main character, but some took things way too far. We're cringing hard at the boss who wanted to brag about bringing the largest amount of flowers to a funeral — what was he thinking with that weird brag? Someone also had a long list of hilarious things their boss got up to, such as doing pushups on the floor to impress potential new hires (presumably they never ever returned to that company!). 

Check out the collection of doofy bosses below. Then, face these powerful final bosses who you can simply never defeat. 

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  • 01
    Organism - garrybibb Ranked all 7 of us in order of his most favorite to least favorite. cervidaes My manager tried to get the nickname he had chosen for himself to catch on. The nickname in question was "Hollywood". He would introduce himself to new workers/visitors/etc. as Hollywood, one of us would say "no one calls him that" and he would just be like "well.... everyone calls me that."
    via Tyronee on Imgbin
  • 02
    Font - r/AskReddit Posted by u/Multicalibrador What's the most Michael Scott-ish thing your boss ever did?
    via u/Multicalibrador
  • 03
    Font - taoshka We had mice. Boss man was terrified of mice and a total skinflint who didn't want to pay for an exterminator. His big idea (I s you not!) was to give me cotton to put in my ears and a blow horn. He then opened the back door, closed all other doors in the little shop, and I had to attempt to herd mice out of the store with a fing air horn, with cotton balls sticking out of my ears. I tried to explain why it wouldn't work, but he essentially told me not to worry my pretty little hea
    via u/taoshka
  • 04
    Font - FridaysOnTheFly I handed him an aerial image I had printed. He told me I needed to reprint it and rotate it 180. I walked to my cubicle, waited a minute, handed it back to him right side up. His reply, "Perfect."
    via u/FridaysOnTheFly
  • 05
    Font - [deleted] It was this guy's last day with the company, and the managers brought in a cake for everyone to share. A very nice farewell gesture. Except he wasn't moving to a new city or leaving the company for a new job. He had gotten fired. The managers literally fired this guy, then called everyone into the kitchen and said "Okay, today is Steve's last day with the company, let's have some cake!" Most oblivious, socially awkward, tone deaf moment imaginable.
    via u/deleted
  • 06
    Font - a Ricetaco After a successful project, owner of the company invited everyone out to lunch (about 12 employees) at a nearby restaurant by the office. Little did she know, the place was very expensive, so she bounces early before the check comes, stating that she had a client call. She gives us money to pay for her meal and takes off, leaving the rest of us to figure out the check. It also turns out she didn't give us enough money to pay for her potion of the check so someone had to throw i
    via u/Ricetaco
  • 07
    Font - 1YearWonder Mandatory Staff Appreciation Day. It fell on my day off, and I had to come in, to participate in the team- building activities that were scheduled. It went from 7am to 7pm, which was longer than a normal shift. That was my only day off that week.
    via u/1YearWonder
  • 08
    Font - [deleted] A few coworkers and I competed in a local Office-themed trivia contest. We came in second place, and one of the prizes was a "World's Best Boss" mug. We brought it into work and displayed it proudly like a trophy in one of our offices. My boss--who was not involved in the contest, has never seen The Office, is not friends with or well-liked by any of us, and is a huge idiot--saw the mug in someone else's office and just took it. None of us could figure out where it had gone unti
    via u/deleted
  • 09
    Font - + [deleted] My boss put candles in his dishwasher to clean them and they ended up melting and distributing a thin layer of wax over everything
    via u/deleted
  • 10
    Font - Amedais We legitimately had to lay off 4 people last year, and management decided to wait until the day before the Halloween office party to do it. No joke. It was like the Halloween episode in real life.
    via u/Amedais
  • 11
    Font - puntini This is a story from my brother. He works at a credit union and one morning around 10 his boss walks out of his office asking if anyone wants the other half he cut off of this huge bran muffin he had for breakfast. Everyone there said they were fine and the boss went back into his office. Later, around 12, an employee comes in for her shift with a box full of doughnuts to share with
    via u/puntini
  • 12
    Font - the office. Everyone came up and took one thanking the employee for bringing in the treat. The boss was visibly mad that everyone went for the doughnuts and no one wanted his half of his bran muffin. He was just a big grump for the rest of the day.
    via u/puntini
  • 13
    Font - Chosen_Fighter Wore a tuxedo at work lunch to give out superlative type rewards. The lunch was at a local sports bar. He had never seen The Office.
    via u/Chosen_Fighter
  • 14
    Font - cervidaes My manager tried to get the nickname he had chosen for himself to catch on. The nickname in question was "Hollywood". He would introduce himself to new workers/visitors/etc. as Hollywood, one of us would say "no one calls him that" and he would just be like "well.... everyone calls me that."
    via u/cervidaes
  • 15
    Font - [3+4) Smiling_Mister_J As a blizzard approached, he offered to drive home anybody who needed a ride because he'd just bought Hummer a new "bada H2 that "could drive through anything". And hour later, he and three of my coworkers are sitting in his new SUV in a snow drift on the side of the road, waiting for the wife of one of them to pick them up.
    via u/Smiling_Mister_J
  • 16
    Font - My one boss, an absolute nightmare of a human, carried all of his paperwork around in a black trash bag. And he was rich, like filthy rich. he inherited his father's contracting company and during the boom of the early 2000's made a ton of money. But he said he didn't trust briefcases... yeah, i know. So one night he left his trash case in an office and a cleaning woman threw it out. All contracts, building specs, whatever, gone.
    via r/AskReddit
  • 17
    Font - [deleted] Asked an interviewee, "Aren't you a little old for IT?"
    via u/deleted
  • 18
    Font - SteveDonel We were having rounds of layoffs every 3 months; an older electrician was being let go, but had not yet been told. A lower level HR guy walks into the cafeteria and says "Sorry to hear your being let go, I guess you're just to old" I have never seen so ups in a many single sentence. 1. telling him before HR had even informed his supervisor 2. Informing him in front of all his co-workers
    via u/SteveDonel
  • 19
    Font - 3. Telling him that he is being laid off for illegal reasons 4. HE WORKED IN HR so he should know that all of these are a problem
    via u/SteveDonel
  • 20
    Font - Hrekires made someone come with him to get his shoes shined because he wanted someone to talk to. except, we all wore sneakers, so the lucky guy got to just stand there and wait while he got his shoeshine.
    via u/Hrekires
  • 21
    Font - mikejones0771 Had us rank each other in order from 1 to 20, of who is the overall hardest worker. Told us no one would know the results. Next day, reads the order out loud. The people ranked 15-20 now knew what everyone thought of them. Killed staff morale.
    via u/mikejones0771
  • 22
    Font - ngomong We had a particularly demanding client and a couple of the project managers were having trouble keeping him pleased. After hearing them complain, Larry, the boss, pulled out his flip phone and said "let's call him right now" and put him on speakerphone. After making a show of being the "tough guy" and putting him in his place, he got in the last word, flipped the phone closed, and put it in his shirt pocket.
    via u/ngomong
  • 23
    Cheezburger Image 9771837440
    via u/ngomong
  • 24
    Font - offhandaxe He was approved to buy a furniture set for out new office waiting room he bought one then took it home and brought his old living room furniture for the office to use. Then when they shut that office down a year later he took his old furniture back instead of letting them take it to the new office location.
    via u/offhandaxe
  • 25
    Font - hoilst He cooked us lunch. This was at a mattress store. This was meant to be a reward/incentive because, quote, he was "a f kin' good cook". He would cook us "the fin' best meal youse have ever eaten". He built it up all week.
    via u/hoilst
  • 26
    Font - We did not have the facilities for cooking, so he cooked us chicken burgers in a vertical grill. Dodgy, pub-grade chicken burgers, that only the dodgiest, scummiest pub would ever sell as like their Tuesday $5 lunch special. Later, when he was out of the store (because he was always out of the store), we were out the back all smoking, and we just sort look at each other. I said, "We...we only ate that out of sympathy, right?" "Yeah."
    via u/hoilst
  • 27
    Font - billbapapa Not my boss, but a guy created a few scholarships at the university I was at, and then something weird happened, like they were supposed to be 4 year deals, but he only had the money for 1 year... Anyways, when it happened I remembered someone saying he "Scott's Tots"ed them...
    via u/billbapapa
  • 28
    Font - Gumburcules Every year representatives from my old company would attend the International Bridge Conference in Pittsburgh. The first year I went, my boss got me all hyped because there is apparently a restaurant in Pittsburgh that it was his tradition to go to every year when he was there for the conference. He kept saying how exciting it was that he could introduce me to the tradition so I figured it had to be some awesome unknown local gem or at the very least a Pittsburgh icon like Pri
    via u/Gumburcules
  • 29
    Font - [deleted] We work in digital marketing. He stalks our coworkers on social media and brings up their posts at weird times. We'll be in a meeting and he'll bring up someone's weekend plans from a month ago, in front of everyone. Most of the time he's not even friends with these people. It's so awkward and cringey.
    via u/deleted
  • 30
    Font - garrybibb Ranked all 7 of us in order of his most favorite to least favorite.
    via u/garrybibb
  • 31
    Font - TheGreenShepherd. I honestly don't know if this is Michael Scott behavior, but this was absolutely bats insane and I don't know how else to categorize it. Context: We were having an all-hands meeting where the CEO of a small company (50-ish employees) announced that he had just fired the CFO for "embezzlement." We all knew he was full of sand he fired the CFO because she disagreed with a decision.
    via u/TheGreenShepherd
  • 32
    Font - Anyhow, right after he announced this, he offered $100 as a "morale booster" to anyone who could sing the entire Tigger song from Winnie the Pooh. Yeah. So, one brave girl gets up and starts singing the whole song. She gets to the last line and messes up one word. The CEO says that it doesn't count, pockets his own $100 bill, then proceeds to sing (and dance to) the whole song while we stand there, watching him, mouths agape. When he finishes, striking a maniacal pose with, "...and I'm th
    via u/TheGreenShepherd
  • 33
    Cheezburger Image 9771837184
    via u/TheGreenShepherd
  • 34
    Font - • He'd come in while we were trying to work and challenge us to planking and squat contests. No one ever took him up on the offer, but he'd still plank and squat just the same. Hard to focus on coding when the guy who signs your paycheck is 3 feet away from you, covered in sweat, grunting and groaning like he's in labor. • After firing the CFO, he took it upon himself to handle all hirings and firings. We found out that this usually meant that he would Facecreep the candidates and only br
    via u/TheGreenShepherd
  • 35
    Font - women of a certain 'caliber'. He rarely hired men unless they were on the dev team, like myself. • He was very into cycling and would often wear only his cycling outfit the entire day. Coupled with his lack of understanding of personal space, this resulted in highly awkward situations. • We once walked past his office when he was conducting one of his "hot girl" interviews, only to see him on the ground, doing push-ups in front of her.
    via u/TheGreenShepherd
  • 36
    Font - • He highly encouraged us to join the gym, offering to let us wear our workout clothing if we exercised at lunch. But then he would give us men a hard time about it. It was clear he only had the policy to see the girls wear skimpy clothes, which they never did.
    via u/TheGreenShepherd
  • 37
    Font - At first he was kind of entertaining. The dude was just noticeably off his nut. But usually, he'd make up for his crazy behavior by doing nice things. I only stayed for about a year, though. He fired the CFO about 6 months into my tenure and he as well as the company, itself-started getting really unstable. I discovered that the company had a huge software licensing issue and when I let him know, he publicly humiliated me. Full-on screaming at me, talking baby talk, scolding me like a bad
    via u/TheGreenShepherd
  • 38
    Font - of all of my colleagues. I should note that I did not approach him to discuss the licensing problems in front of everyone. He asked me what I was working on as I was writing up the report. I tried to be discrete about it, but he kept probing until I had no choice but to tell him everything I'd discovered. I started looking for a new job right away. From what I understand, things got much worse after I left.
    via u/TheGreenShepherd
  • 39
    Font - Goran1693 Was at a funeral for a co- worker's husband (who I was good friends with as well) and my boss came along for support. He had bought a large floral arrangement for it and spent most of the service nudging me on the shoulder and pointing to it in a "Eh? See that? Niiiice right?" fashion. He later went on to brag that he ordered the largest arrangement of everyone in attendance.
    via u/Goran1693

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boss work stories toxic-workplace funny stories askreddit toxic-boss workplace Horrible Bosses funny toxic-work-environment
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