1. Winnie the Pooh: Home Run Derby, a.k.a. Baseball for Masochists
By far the newest game on this list, Winnie the Pooh: Home Run Derby might just also be the most baffling. First of all, it's a Japanese Winnie the Pooh browser game in the 21st century. Coming out in the age of Reddit, 4Chan, and public discussion of psychological fetishes Home Run Derby also inspired a sort of demented internet nightmare cult.
As such the game picked up probably more attention than it otherwise would have. Coverage of Winnie the Pooh: Home Run Derby mostly focused on the bizarre "fan" content the game spawned. Such artifacts as bizarre art, videos, and Wikipedia graffiti. The last of which painted perennial mascot for precociousness Christopher Robin as a vindictive deity.
Most of which has now become hard to find for one reason or another. Which is almost just as creepy all by itself. The idea that the entire thing could just up and disappear lends an urban legend quality to the whole deal. The game itself, meanwhile, pretty much lives up to the status surrounding it.
This game isn't just difficult, it's malicious. Members of the Pooh cast are filled not with stuffing, but the baleful spirits of baseball superstars yet unborn. Sort of like Angels in the Outfield, if Christopher Lloyd didn't want to rejuvenate the spirit of sportsmanship so much as erase it from the timeline.
Owl, Rabbit, Tigger, etc. throw balls at you (that lovable, huggable old golden bear Pooh). You hit them. Or rather, you don't as the two-dimensional meteors fly past in zigzagging arcs that defy all human logic. Even if you do manage to make wood touch leather odds are you'll just wind up hitting a foul ball. So, in that way, it has at least something in common with real baseball.
That the Walt Disney Company of all entities would sign off on this project boggles the mind. Someone almost certainly thought they were making a child's afternoon distraction/magnet to the anachronistic Pooh brand. What they made instead is near the top of our running list for "Most Likely to be Frog Fractions 2."
2. Teenage Mutant Ninja Turtles, an Exercise in Family Friendly Frustration
The Teenage Mutant Ninja Turtles were designed as a satire of the pandering, overly gritty pop culture which was so rampant in the late 80s and early 90s. So it stands to reason they'd be co-opted into a family friendly, child exploiting money machine about 37 seconds after hitting store shelves.
While the TMNT cartoon series and toys were S-A-W-F-T "soft," their very first game was anything but. Sure, it was just as clean and pastel colored as the mainstream version of the ridiculous reptiles. It's just that it was also hard as all hell.
A few facets of Teenage Mutant Ninja Turtles conspire to make it one of the hardest games from the NES. First, there are the enemies. Besides being ridiculously tenacious these buggers infinitely regenerate like they just missed getting hired by Dracula to defend Castlevania. They're also nearly impossible to hit. That is, unless you're playing the one and only turtle worth a damn: Donatello. Whatever you favorite anthropomorphic green ninja (or bandana color) Donnie was the only option in this game of multiple, playable characters. That's because the range of his staff far outpaced his brothers in green.
But, really, it was the sewer sections. Here, as in most of the games "real" stages, the perspective tilts sideways to force your chosen hero in a half-shell through downright insurmountable platforming. Jumping in TMNT isn't a matter of trial and error. It's a cruel joke. A cruel joke with basically a 50/50 chance of actually landing, much like you and your protagonist. Meanwhile, you're still constantly under assault from those never-ending enemies mentioned earlier. Oh, and fuck the underwater level.
In spite of all this the game was a massive commercial success. It sold millions. No doubt thanks in part to the strength of that particular franchise at the time. Though a shall-we-say-generously-high score from Nintendo Power probably didn't hurt its chances. It was enough to get a PC port the very next year, which exemplified just what made the game so memorable. Which is to say it was literally unbeatable without cheat codes.