Friday Conversation: Tell Us About Your Most Horrible Boss

Considering (a) it is Black Friday and anyone who has ever worked retail over the holidays has oodles of horror stories to share, (b) the movie Horrible Bosses 2 opens this weekend, and (c) those first two things make it just barely topical and relevant enough to discuss on a pop culture website, this week’s conversation topic is bosses. Terrible, awful ones, whether they be lazy and incompetent or mini-tyrants mad with power or whatever else you got. Tell us about your worst, most horrible boss. Just don’t use last names, or the name of the business unless it’s some giant faceless corporation. This is about venting, not vengeance.

Below, please find a few tales of workplace woe from the UPROXX staff. I would include one of my own, but after a great of deal of reflection I realized that I never really had a truly bad boss. Even the ones who weren’t all that great get a pass, I guess, because they had to deal with me, and I was a total jackass of an employee through my early 20s. One time when I worked at a golf course I spent an hour whizzing rocks at this light that was maybe 100 feet away. I finally hit it and shattered the bulb, and when my boss came in hungover and grumpy the next morning and asked me about it, I replied “Probably birds.” Birds. He just stared at me for about five or ten seconds, sighed, and walked away. That guy had a right to be a jerk to me.

These stories as better. Leave yours in the comments.

Vince Mancini:

I’ve edited porn, driven a forklift, slanged lattes at Starbucks, worked in the kitchen of a shouty Chinese restaurant, crewed commercial shoots on everything from an ab scissor infomercial to The Real World, and written copy for porn ads, but by far my most horrible boss was my supervisor during my brief gig as an in-house copywriter at a company that serviced college loans. Turns out there’s no style guide for giant tables of loan types and interest rates. Though that didn’t stop this boss from trying to invent her own in her head, which would change every few days. As well as ignoring my attempts to create a written style guide, she’d often forget her previous mandate, so I’d get chastised for following it, screwing up those oh-so-important details like “should a bullet point about Stafford loans have a period at the end of it.”

There was an office tradition of taking people out to lunch on their birthday, but getting to eat my lunch in peace while reading a book in the sun was my only respite from my terrible co-workers, so when my birthday came around, I prayed no one would notice. The day came and went, but the following day, the supervisor noticed. Everyone else in the office had already bailed, so the boss and I, despite our thinly-veiled mutual loathing, went on a one-on-one lunch date that neither of us wanted, out of pure obligation. I think it was Indian food. Not even the most powerful curry could cover up the stench of forced pleasantries. Did I mention she was a huge Ben Roethlisberger fan? Yeah.


My first job out of college was for this “up and coming, high end” lifestyle magazine, which was a really fancy way of saying that it was filled with articles about stuff that people were willing to pay us to write. I didn’t know squat about the “business” when I started working for this British dickhead of a publisher, but this guy thought he was the male version of Anna Wintour, in that everyone should have been kissing his ass because he had an accent and drove a Mercedes. At one point, we set up a fancy-pants event and had Padma Laksmhi as a special guest. I can only imagine what she thought when she saw the 90 or so people who showed up.

Anyway, while this dude thought the world should be sucking him off, he was a classic leech and con man, who had nothing going for him except for the ability to trick our ultra-wealthy publisher into giving him a ton of money that he basically kept for himself. It was truly impressive the way he tricked us all into thinking he was even remotely intelligent, but he was a total asshole. After the landlord of our office building let us into the padlocked office that this dick hadn’t paid rent on for a year, he called us on the conference room phone to lay us off. The best part was him pretending that he didn’t tank the magazine out of sheer incompetence.

A few years later, he was rumored to be working sales for some niche magazine in South Florida, and I saw his wife at a restaurant in Orlando. She looked really tired. I didn’t say hi, but I left with the idea that she had beat herself up for years over the idiocy of marrying a cheating, lying, pathetic scumbag. I couldn’t have been far off.

Cajun Boy:

When I moved from Louisiana to NYC years ago to pursue my dream of running a website (kidding, that was not my dream at the time, but whatever) I needed a gig to put some money in my pocket for food and shelter and such, so I found a job through a temp agency working for a real estate guy who ran his own one-man operation. I was his assistant, essentially, and he was — for lack of a better way to put it — the embodiment of many bad New York Jewish businessman stereotypes. For sake of the story, let’s call him “Goldstein.” He was pushy, rude, cheap, insecure, vindictive, kinda shady, etc., on top of being a bit of a slumlord.

After working for Goldstein a few months — longer than any employee of his had previously lasted — he began to court me to come to work for him full-time, to be a partner, essentially. I, of course, politely refused because getting involved in real estate was not the reason I moved to New York. This baffled Goldstein. He simply couldn’t understand why I’d want to pursue a passion as a career rather than something that had potential for greater and more immediate financial benefit. All Goldstein cared about was money, you see, and he seemed incapable of comprehending how I was not as equally obsessed with money as he was.

So one day, presumably in an effort to make me see the error of my ways and turn me to his way of thinking, Goldstein came into the office — a cramped, coffee-stained, overflowing-with-paperwork space in a Midtown Manhattan high rise — and made a declaration.

“From now on I’m not going to call you by your actual name,” Goldstein said. “Starting today I’m going to call you ‘Cajun Boy.’ And I’m going to continue to do that until you let go of the pipe dream of becoming a writer and come work full-time for me doing real estate.”

And so he did. Goldstein called me “Cajun Boy.” “Where’s that contract, Cajun Boy?” What are time are you showing that apartment, Cajun Boy?” Etc. He’d even introduce me to his associates as “Cajun Boy.” It was some sort of weird attempt at mindf*ckery, to try to shame me into coming work for him or something. It went on to become a big joke amongst my friends, so it evolved into my nickname, of sorts, one that stuck long after I’d quit working for him. And when I decided to stick my toe into the murky waters of the internet by starting a personal blog in late 2006/early 2007, it became my online identity.

And the rest, as they say, is history.

Andrew Roberts:

The worst boss experience I’ve ever had was while I worked for the now departed Waldenbooks. I took advantage of their employee discount whenever I could, but the boss at a neighboring Borders store gave me sh*t once for trying to use it at their store. I wasn’t working at the time and I certainly wasn’t working for him, but he proceeded to dress me down at the counter and ask if I had actually read my employee handbook. I had not.

This caused him to get upset and he threatened to call my actual supervisor at the store, claiming they were buddies and a few other things. I gave up and left without the book I was trying to buy, but I never forgot what happened.

That’s part of the reason why I would always go back to their store and leave erotic novels and sex books in the kid’s section. You might think it is wrong to damn a store because of one guy, but I really didn’t like anybody at that store. Good riddance.

Jason Tabrys:

When I was a younger lad I had a habit of sitting on the job. This did not please management and, according to one of my bosses, loss prevention was asked to compile a 45 minute long supercut video of me sitting on the job. I assume that this was done to usher in my dismissal from the company (though, I later left on my own terms). I don’t know if this is technically a horrible boss story (since I was in the wrong), but it’s plenty weird and I would LOVE to get my hands on that riveting video tape.

Stacey Ritzen:

I experienced a great deal of degradation from bosses during my collegiate waitressing career including one 40-year-old restaurant owner who aggressively hit on me until I quit, to another who threw a bread basket at my head because I didn’t know where they were kept. (It was my first dinner shift!) However my worst boss ever was a few years out of college, when I worked as an art director for a small family owned and operated advertising agency.

They were the kind of people who were very, very active in their church but behind closed doors treated their employees like indentured servants. Part of my job duties included assembling powerpoint presentations for my boss’s church board meetings. At one point while he was out of town on business, he had a woman pay me a surprise visit about designing some collateral for a local charter of a “Homosexuals Anonymous” group that a few of their church members were starting up. OH, IT’S EXACTLY WHAT YOU THINK IT IS.

When they finally let me go, on New Year’s Eve mind you, they told me in a sympathetic tone that they were waiting until “after the holidays” to cut me loose, as if they were doing me a grand favor. NOPE. New Year’s Eve is still “THE HOLIDAYS,” jerks. My health insurance also terminated January 1st, so that was nice of them, too.