The King of Chicago is a strategic gangster simulator, released by Cinemaware in 1987. And – while “gangster simulator” might sound bad – the game is full of dark humour and is something of a satire, so is not to be taken too seriously on that front.

You play a young, ambitious wiseguy in 1930s Chicago who must work his way up to the top in The Organisation. You do that by initially towing the line and doing ever-increasingly dangerous jobs for the mob, until the time is right for a bloody coup… There are cops to keep off your back, and a demanding girlfriend to appease, so other challenges to consider as you progress.

Although The King of Chicago is a very good game I have to point out that the graphics – in particular the human figures – are laughably bad in places. I guess it kinda suits the satirical nature of the game, but it is one of the few Cinemaware games that I’ve looked at and gone: “what the hell is that all about?!” Still, at least the gesticulating characters look funny…

Surviving in The King of Chicago is not easy. Most of the decision-making sequences take the form of thought bubbles that you can click on, and some are time limited, so if you ponder too long you can lose a chance at a particular moment. As always, with games like this, making the right choice at the right time is key. Also, luck plays a big part of your success – maybe too much… If you do get stuck, there are always guides.

See also: Cinemaware Special

More: The King of Chicago on Wikipedia