The street where you live

I played the original SimCity game on a monochrome screen - I couldn't even find a gameplay video from a version that old to post here - and spent many a happy hour laying out public transit lines in my growing metropolis, and positioning my police stations for maximum urban coverage. One time, many years later, I even tracked down game designer Will Wright to pester him with a question about the economic importance of fire stations (he never answered). 

I haven't found a simulation application I've enjoyed as much since. If you've ever watched your carefully-constructed urban core devastated by the sudden appearance of a kaiju-style monster, and realized you can use the opportunity to blow a highway that's marring your city's perfection, you might enjoy this piece on the history of city simulation games