Boss's Day is October 17th this year. Are you prepared? If your boss is humorless, it's probably for the best that you don't shop off of this list. For those with a joker in charge (or those of you who would like to fantasize about giving your supervisor a strange and perhaps even passive aggressive present), here's eight gifts sure to be welcomed by the big cheese.

1. Deal With This Stamp


Lots of paper pushing at your office? Your boss might get a kick out of sending your reports back for corrections with a big, fat Deal With This Stamp ($9.79). For the more brazen boss, consider the WTF Stamp ($9). A word of warning: you will probably grow to regret ever letting your supervisor get a hold of this thing.

2. Things You Must Do to Make Me Happy Notepad


Looking for more specific feedback, or how to avoid unpredictable moods? Let your boss check off what he or she wants on this Things You Must Do to Make Me Happy Notepad ($6.99)—although I must say, some of these check boxes look like a sexual harassment lawsuit waiting to happen.

3. Steve Thomas Office Propaganda Posters


If your boss runs a tight ship, he might appreciate these office propaganda posters ($27.10) by Steve Thomas. If his lush corner office is already well decorated, these retro prints come in mousepad form ($13.15) too.

4. "I'm Having a Bad Day..." Mug


Not everyone's boss is a ray of sunshine. If she's more of an Eeyore than a Piglet and is never optimistic about the company's future, consider this mug by Daily Grinder ($14) that celebrates her inner masochist.

5. Dark Chocolate Covered Potato Chips


Does your boss frequently visit your desk, only to violate that candy jar you keep next to the printer? Perhaps you should drop a hint and give something he can munch on, like Dark Chocolate Covered Potato Chips ($17). They might sound weird, but there's something special about a mix of sweet and salty. If anything, they'll be something to talk about around the water cooler aside from Dancing with the Stars.

6. What's for Lunch Spinner Game


Speaking of the ever hungry boss, if you're tired of her always having the final word about what to order in for lunch, attempt to spice things up with the What's for Lunch? Spinner Game ($5.99). A random spin may be unpredictable, but at least it means you don't have to eat that lousy Chinese take out she swears by.

7. Office Monkeys Play Set


Ever get the feeling a room full of chimpanzees on typewriters would be more productive than your office? Ever get the feeling that your boss knows it? If that's the case, maybe you shouldn't gift this Office Monkeys Play Set ($19.50) or HR will finally bring in that office restructuring specialist they've been talking about...

8. Bo$$ Pimp Cup


What else needs to be said here? It's a pimp cup that says BO$$ ($19.99). I don't think it's intended for hot liquids—a shame, because this thing would be a fabulous way for your boss to enjoy that first cup of coffee in the morning.

Don't think your boss has the sense of humor to take these gifts? Check out our Boss's Day coupons page for more traditional gift ideas.