Jack the Nipper is a side-view flip screen game with puzzle solving and platform elements. The graphics are rendered in 2D, but an illusion of depth is achieved by allowing characters to move forward and back within the playing area. The player controls Jack, a naughty child who wants to break the record for naughtiness (recorded on the "naughtyometer"). He needs to carry out various wicked pranks on the unsuspecting inhabitants of his town, but if he comes into contact by angry adults he will be spanked. With each spanking his "nappy rash" meter increases, and if it grows too high Jack loses a life. Contact with the monsters and ghosts which inhabit the town will also increase the nappy rash.
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