Rating: E10+ (and a hard one at that)
Players: 1-2
Price Range: ~$53 USD
Okay, before you get your pitchforks ready given how high I put this, hear me out.
I'm not saying that Shadow the Hedgehog is a good game, in fact, it has some of the worst design of any of the games on this list.
The gameplay can be obnoxious, the story is incomprehensible, it is way too dark to warrant a E10+ rating, as there are damns, guns, and the literal White House gets blown up, and it has some of the worst levels I've ever played in a video game. The two Ark missions are some of the most convoluted, confusing, and outright miserable stages in any platformer, as not only do they just not work, as one of them required you to interact with a GUN soldier, only for them not to appear unless you use the checkpoint system to coax the game into spawning him but they are legitimately terrible. The one that tasked you with killing all the artificial Chaos monsters took me over a half hour to complete given how the copy and pasted hallways made the whole place a maze, and the only way I could have competed it is from watching a walkthrough on the internet and find out that I missed on in one of the turret sections, realizing that I missed it since they only become visible when you are close to them.
What an abomination of two levels.
So, given the game's clear issues, why did I put it this high?
Well...
If there was a single description I would give Shadow, it would that I think it is The Room of video games.
It is so uniquely terrible, that the game somehow hypnotizes you into thinking that it is actually good.
Yeah, they reuse stages, some more egregious than others, and the plot may make no sense, but it is so laughably incoherent how the characters make such dumb and haphazard decisions like a poor imitation of a "choose your own story" where none of the ending minus the true final ending counts at all while make no logic whatsoever, that it is actually hilarious.
It is fanfiction, but it is dumb, stupid, and hilarious fanfiction.
The way that they try to make it as dark as humanly possible and yet still get away with an E10+ rating is just too funny. A literal anthropomorphic hedgehog killing aliens with guns and an actual knife despite how useless it is in-game. Priceless.
And come on, Shadow can hold a grenade launcher with one arm like a pistol, and he can carry an absurdly long gatling gun one-handed while running fast. Hilarious.
Also, the game has genuinely great moments as well. The music, especially the intro and true credits theme, are actually really good, and a few of the levels, like Lava Shelter, are decent, and the gunplay is enjoyable, even if it doesn't belong at all in a Sonic game.
Also, as a person who never really got into Sonic, the game is overall terrible, but it is the good kind of terrible.
This reinforces my mindset for video games.
I would much rather play a heavily flawed game if there are some unironically good elements and ideas if it is different from the rest of the pack instead of mechanically perfect, but run of the mill ones that don't stand out at all.
Also...
The multiplayer sucks...a lot.
It is not only an afterthought, but there are many useless characters that can only hold the weapon they spawn with, only allows for two players as opposed to four, and makes the game somehow run worse than usual.
Still...
Overall, Shadow is a mess, but it is a fascinating mess that makes so many bafflingly wrong design decisions and those issues are only in this game. That is why it is this high, along with the actually decent elements of the game.
Not a recommendation at all, but for those who share my view on this game, like a laughably bad movie, it is entertaining.

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