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Chicago Enforcer places the player into the position of a mobster attempting to work his way up through the mafia in Chicago, circa 1930-1940. The mobster's story and subsequent promotions form the basis of the plot.
The gameplay is geared mainly toward a run and gun type of gameplay, with a heavy emphasis on guns to achieve the aims of the missions, which were criticised for being highly repetitive, as well as ludicrously long.
The game was widely criticised for having enemies who's AI was not only inept, but also able to remain alive with several gunshot wounds to the body. In addition to this, the police in the game are overpowered to the point that bosses become easier to kill than a carload of police officers. Also, the pedestrians (of whom, admittedly, there are few) cause the game to end if one is killed, by accident or design, resulting in the player loading from a save game or restarting the game.
Another criticism was the ability of weapons such as the shotgun to fire as accurately as the sniper rifle over a distance of several hundred metres, and the gangsters weapons being either hugely underpowered, or doing large, disproportional damage to the player.
The audio in-game is practically non-existent, with little to no music, small amount of voice acting and generic weapon fire sounds. However, the voice acting has been said to be the game's one high note, with the voices being authentic and fitting to the game, and the dialogue being above average
According to GameSpot, Chicago Enforcer has some of the worst character models seen, as well as "horribly bland textures, blocky character models that animate about as well as animatronic robots with broken limbs, and environments so sparsely populated with proper scenery or the aforementioned terrible character models that you would think you had entered some kind of post-nuclear wasteland" . Also, the loading times for the cut-scenes take upwards of a minute to complete.