The title pretty much explains things, so let's get to the creepiness.
#1. Don't Wake Daddy
This is the creepiest game of all games. You play as a group of kids that wake up very hungry in the middle of the night. You take turns trying to get to the fridge to gain nourishment, but you have to be careful because if you accidentally wake up your dad, you lose.
Why is this father refusing to feed his children? They have to creep around after he's asleep just to eat? If a dad woke up in the middle of the night and saw his children desperate for food, he'd just make them a snack! And if you don't think he's a monster then explain to me where the mother of these children is. Looks like he's killed once and he's ready to do it again.
Don't Wake Daddy – Amazon
#2. Gooey Louie
I can almost guarantee your parents absolutely hated this game. You didn't really get it as a kid, but as an adult you realize how stupidly creepy this game is.
Gooey Louie is apparently a guy with terrible sinus problems and no arms, so you have to pick his disgusting nose for him. But be careful because if you mess up, his freaking brain will fly out of his skull. It's things like this that make you realize how much we romanticize the 90s.
Gooey Louie – Amazon
My parents wouldn't let me watch movies with violence in them, but they had no problem letting me solve a murder that involved one of the people I'm playing with taking another friend to a quiet part of a mansion and beating them to death with a pipe. That's super chill!
Clue – Amazon
Monopoly is a great way to waste three hours and end up despising your dad for becoming a ruthless tycoon. The entire concept of the game is to destroy every small business and increase the cost of expenses for everyone else, until you're the only viable option in town and your competitors are left penniless with nowhere to live. You're pretty much Michael Douglas on the movie Wall Street.
Monopoly – Amazon
Just like Shark Attack, this game put you in the role of a tiny, cute creature just trying to survive. However, in Shark Attack, the shark just ate your game piece. In this one the bug you built out of dough gets smashed into oblivion! Look at that green bug staring on in horror as he witnesses his friend getting murdered right in front of his face.
Splat! The Bug Squishin' Game – Amazon
#6. Guess Who?
The concept isn't creepy, but what is really troubling is that there is exactly ONE black lady and one guy that might be black or is just in a dimly lit room. By saying, "Is your person black?" You eliminate 1.5 characters and that's it. Guess Who? More like Guess Who's Really Racist?
Guess Who? – Amazon
#7. Shark Attack!
You each play as a small fish desperately trying to swim away from a massive, furious shark that's trying to eat you and kill you. That's definitely not a surefire way to have massive amounts of anxiety.
Imagine the pitch for this game. "Kids will love fighting and clawing their way through water sacrificing their friends and siblings in order to survive!"
Shark Attack! is an out of stock vintage board game from 1988 but I've seen a few on eBay if you want to get it.
Some jacked up guy comes to the hospital because his body is in shambles, so instead of having an actual physician work on him, they turned the responsibilities over to a bunch of bored children that take turns ripping random parts out of his body.
If your hand shakes in the least bit, it would buzz and shake, to simulate the patient screaming in agony. Worst of all, he's wide-awake during the whole operation. It's basically Saw 4.
Operation – Amazon
#9. Hungry Hungry Hippos
Four hippos are starving because they don't have any legs and just sit there praying that they get a chance to eat. So instead of giving them food, you dump a bunch of marbles in front of them. They don't want to eat, so you punch them in the back over and over until they obey you.
When you really think about it, this game is depressing and horrifying.
Hungry Hungry Hippos – Amazon
#10. The Game of Life
There is nothing more troubling than hearing a sad child announce that he just lost at Life. Get ready kid, there's plenty more where that came from.
The Game of Life – Amazon