Draw a line forming the outline of the buildings. Only use straight lines going up and down, making buildings of many different sizes. Really try to have variety amongst your buildings, or else your cityscape will be pretty uninteresting.
Add a second row of buildings drawn in front of the first. This will add depth and perspective to your cityscape; just make sure you keep everything in proportion and if you mess up, erase very carefully so as to not smudge any part of the other sketched row.
Color the back row of buildings in a lighter shade of grey than the second, and paint the sky as though it were dawn. If you add more rows of buildings, remember that the farther they are into the distance, the brighter the shade of grey they need to be.
Add details like random lights turned on in the buildings. Use rectangles and squares to mimic the windows. Put many together in groups for larger buildings to make them look like apartments, and for warehouses and similar structures don't add any light at all.
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