The 9 Most Annoying Bosses You’ll Ever Work For, Ranked

Today, October 16th, is Boss' Day, an ill-conceived national holiday that has nothing to do with Rick Ross.

In case you’re unfamiliar, Wikipedia sums up the annual occasion with precision: “It has been pitched as a day for employees to thank their bosses for being kind and fair throughout the year, but some have opposed the concept as nothing more than a meaningless Hallmark holiday, as well as placing unfair pressure on employees to kowtow to managers who earn more than they do while exercising power over them.”

Boom, roasted.

The holiday originated in the 1950s, when a nepo baby working at State Farm wanted to honor her dad, who also happened to be a boss. Had she never heard of Father's Day? Sadly, we will never know.

In honor of Boss’ Day, LEVEL compiles the most annoying bosses you may encounter today, and every other day of the year that is not a workday or (real) holiday.

9. Janice, Who Is Not an Actual Boss

Has tenure with the company and thinks that entitles them to pull rank and boss others around. Will rat you out because they snitch.

8. Pete, the Pizza Party Boss

For every big accomplishment, they'll give you pizza. Instead of a raise. Or a bonus. Or a day off. Enjoy the pizza!

7. Irene, an Invisible Boss

This boss is at the golf course "networking," takes days off and doesn't tell anybody, and calls you from France to tell you, "Oh, by the way, I'm in France."

6. Mr. Edwards, the Enabler Boss

Encourages bad, bro-y behavior and lowers morale by playing favorites. Spoiler: You're not their favorite.

5. Greg, the Gossiper

Talks s**t about everybody and plays you all against each other like they're hosting Survivor. Hiding a terrible secret: They have no life of their own worth gossipping about.

4. Diana, the Dictator

Mean, spiteful, and makes you work overtime without extra pay. Wants everyone to be as miserable about work as they are in the office. Guess what? That's starting to happen.

3. Lenny, the Lecherous Middle Manager

Touches shoulders, sends pervy memes, gets drunk and tries to score at the office Christmas party. Will get fired when all the porn in their browser history is discovered.

2. Micromanager Mary

Sends work texts at all hours of the night and morning and asks to be cc'd on emails. Doesn't trust you to do your job properly, so they try to do it for you and then get stressed about it and b**ch at you in front of your coworkers.

1. Bob, the Boomer Boss

Wants you at your desk a minimum of eight hours, five days a week—and much more if there's a project due. No personal photos at your desk, no coffee breaks longer than 15 minutes. Keeps talking about the good old days when there was no diversity hiring or women in charge. Word to Will Ferrell, this guy's oooooooold school.

The 9 Most Annoying Bosses You'll Ever Work For, Ranked