Fun trivia: Chaos In The Windy City was designed by Amy Hennig, who went on to write the Legacy of Kain series (from Soul Reaver onward) and is currently Naughty Dog's creative director. Sometimes what happens (or at least what used to happen) with these celebrity-endorsed games is that the company lands the endorsement deal without actually having a specific game design in mind, then they'll go fishing around for some half-completed project or something someone is toying around with that looks halfway promising to slap the celebrity into and not worry too much about the overall quality or if the concept even makes a lick of sense. As long as it was considered a halfway passable effort by a significant share of 8-year-olds, it would rake in the $$$ anyway solely off of star power.

The point of all this rambling being that the game was developed by someone who went on to prove they can develop a really good game, so if I had to lay a wager I'd say this is what happened here. This was a platformer idea that was maybe being kicked around the bowels of EA's studios and had some promise, then some marketing exec ran in and said "HEY WE NEED A MICHAEL JORDAN GAME. USE THAT ONE. THAT ONE RIGHT THERE THAT IS ON YOUR SCREEN. MAKE IT BASKETBALLS." There's no way to know this sort of thing unless an ex-employee wants to do a tell-all interview or something, but I don't think it's an unreasonable guess.

Chaos In The Windy City is an ambitious platformer that actually shows a lot of promise, but feels like it was pushed out the door way too early and without enough polish. It aims higher than the standard Ocean/LJN fare of the period by having non-linear levels that require backtracking, a Mario World-esque world map, and even minor puzzle-solving elements and dialogue trees. Unfortunately, it's saddled with the standard Ocean/LJN fare's sloppy, slidey play control and often thoughtless level design and enemy placement.

So the premise is that Michael is going to meet up at a gym in Chicago with some of his (unnamed to save licensing $$$) NBA buds for a late-night practice game. When he gets there, however, instead he finds a ransom note from some mad scientist asshole and portals to another world full of mutant spiders and surprisingly gruesome basketball-themed monsters. His buds have been locked up throughout this world, he has to first locate their cells, then find the appropriate keys to open their doors. This involves traversing various levels with the occasional boss battle thrown in. Michael's main defense is hucking an unlimited supply of basketballs at the enemy, and can pick up more powerful ball variants such as a flaming ball, a freeze ball and even some inexplicable giant baseball that boomerangs back to you. He's got unlimited regular balls, but the more powerful balls come only in finite quantities.

So you have a game that kind of feels like The Goonies 2 meets Michael Jackson's Moonwalker. The premise is bizarre and completely stupid, and would have come off better if it were played for laughs rather than so seriously and straightfaced, but neither of those things is really a major problem for the game. What drags it all down is just the usual floaty and sloppy play control that halfassed 16-bit platformers were infamous for.
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