Takeshi's Challenge is a bizarre, technically open-world game where you play as a salaryman who gets fired from his job, then is turned out to wander the streets of a limited swath of Tokyo. There's no clear goal whatsoever, and while wandering the streets you are subject to random attacks from some Radical Yakuza Dude and police officers (the former of which will also sometimes attack you if you enter the bar and seems to respawn there infinitely).

Going by the Japanese packaging, which does give you fair warning that the game is impossible to finish, this really appears to be the first attempt at an intentional troll game from a commercial publisher. It's licensed by Beat Takeshi, who at the time of this game's release was doing a popular Japanese "obstacle course" show, but would shortly after this transition into being a Clint Eastwood-like action movie star. From reading notes about the game's development, my best guess is that Takeshi was just bombarding the design team with all sorts of crazy ideas off the top of his head without understanding the limits of Famicom technology, and the design team tried to hack something together that at least vaguely corresponded to all of his requests.

Whatever the case, while the end result's gameplay actually isn't among the absolute worst of the 8-bit library, the combination of confusing goals with the god-awful repeating five-second music loop makes this one really hard to take. I don't know if it actually deserves the reputation of "worst NES game ever" (I can think of at least a few worse ones offhand), but it ain't good.
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