Rags to Riches (1985)

Rags to Riches may be called a "bum simulator", in that it lets you live life as a bum trying not to starve on the streets of a modern city. You start your week with barely any money and nothing to eat, and then you'll try to work your way to the top by getting a job (and maybe, cutting your hair and beard to get a decent one), selling empty bottles and trying not too drink too much in the process. If you play your cards well, you might even end up on high street, where rich people live. But be careful, policemen do not like bums to wander around in rich streets and will do their best to hunt you down and put you in jail. Also, thieves have no respect for you what so ever, and will rob you of everything you own, even those few bucks you found lying in the gutter.