Crazy, Funny, General

The 8 Worst Bosses To Work For

Between having to show up at work and having to actually do work, no one likes having a job. But it doesn’t get any worse than working for one of these eight annoying bosses.


DESCRIPTION: This boss thinks that happy employees are productive employees. But, sadly, he also thinks treating you like one of his frat buddies will make you a happy employee. So he’s always inviting you out for drinks or over to his house on the weekends. What he doesn’t realize is that “hanging out” with your boss is a lot like “work.” And no one likes that.


BEST FRIEND BOSS: (As he’s playfully punching you in the arm.) What’s shakin’ sport?!?! You catch the game last weekend? Hoo boy, sure was a doozy. We missed you down at Applebee’s, man. It was seriously off the chizain. Yes!

YOU: Yeah…sorry I missed it. Sounds like a good time.

BEST FRIEND BOSS: No worries, pal. We can totally bro-down this weekend. (He gets you in a headlock.) I am not leaving Applebee’s until I see you pound a bucket of suds! Or your fired! I am totally kidding, bro. But you gotta show up, man. Yes!

YOU: Well, I was going to just watch the game with my kids. I don’t get to see them as often…

BEST FRIEND BOSS: Bring ‘em with you! Show ‘em what the old man can do!

YOU: But, I…

BEST FRIEND BOSS: (slowly lets you out of headlock) Hey, not to bring it down, but do you have those Jenkins files ready? I really need them for my quarterly report to the board of trustees this Friday.

YOU: I’m almost done with them. Should have them to you by Thursday.

BEST FRIEND BOSS: No problem, pal! Don’t want you think I’m “the man” or anything. I’m just one of you…the little cogs in the wheel. Yes sir. Salt of the earth. But seriously, Applebee’s! Think about it! Yes!


DESCRIPTION: They treat every decision in the office like they’re a 17-year-old girl at a slumber party deciding whether or not she should lose her virginity to her boyfriend of three and a half years. They have complete disregard for the fact that you might actually be working on something important, and instead interrupt you so that you can weigh in on whether or not the font on the business cards should be changed.

(You’re quietly working at your desk when a tap is heard on the wall next to you)

WHAT DO YOU THINK BOSS: Hey, you busy? Can I pick your brain real quick?

YOU: Actually, I’m right in the middle of-

WDYT BOSS: Soooo, I got this e-mail from corporate about this seminar for increasing productivity. They said I didn’t have to go, but I don’t know. What do you think?

YOU: I don’t know.

WDYT BOSS: They want me to go huh? They wouldn’t send it if they didn’t want me to, right?

YOU: I don’t know.

WDYT BOSS: Yeah, you’re right. I should definitely go. Thanks.


DESCRIPTION: No matter what you do, this boss is always an impossible-to-read silent, stoic rock. Is he happy with what you’ve done or is he on the verge of firing you? You could turn in your best work yet, stay late, go the extra mile, but this boss never shows any gratitude and instead just treats you like a disappointed dad.

YOU: Here’s the report you asked for.


YOU: I made collated color copies and bound them by hand using a rare Indonesian leather. I also created customized covers for everyone who will be at the meeting using their high school yearbook photo and 14 karat gold calligraphy.

SILENT BROODING BOSS: Leave it on my desk.

YOU: Also, I went ahead and paid for a sky writer to write the name of our client’s company in the sky right as the meeting is finished. I paid for it myself, just to cut costs, ya know. I’m always thinking about that.

SILENT BROODING BOSS: That will be all.

YOU: Tell me I did good


YOU: Sorry. I’ll be at my desk.

Read about the 5 worst bosses at Holy Taco.