TABOO: THE SIXTH SENSE / Rare / NES
I'm pretty sure some asshole at Rare made Taboo solely to confuse and frighten children. It really shouldn't even qualify as a "game", because the only interactive part is at the beginning where you enter your name and birthdate (and laboriously write out a question that the game proceeds to completely ignore.)
Basically, it simulates a tarot card reading to tell your fortune. The game was marketed as "not for kids" (WINK WINK KIDS), but their conception of "maturity" apparently just meant being depressing as fuck. I swear, nearly every time you run this game it finds a way to tell you that you're a horrible person and some tragedy is waiting to befall you.
Oh, and it does one other thing - gives you "lucky" lottery numbers after every reading. So aside from wasting your time and money, it's also exhorting you to gamble at the worst odds possible. What a class piece of software.
Everyone who paid retail for this game drew this card
This is the kind of thing you might get away with in the App Store priced under a dollar or something, if it had nicer graphics and the text wasn't garbled Engrish (made all the more bizarre by this being made by Rare ... a British company). This thing retailed for forty 1988 Dollars when it came out, though. I can't imagine a harder kick in the jimmy than saving up your allowance or something for months, buying this on a whim at the store, then finding out it just makes your Nintendo give you dumb advice and tell you you're going to get sick.
* Gameplay Video