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The object of Paperboy is to deliver papers to your customers while inflicting as much damage as possible to the houses of your non-customers. To make things more difficult, numerous obstacles get in your way including construction workers, rogue tires, skateboarders, dogs and cats, cars, and even the occasional tornado.
The player controls a paperboy on a bicycle delivering newspapers along a suburban street which is displayed in a cabinet perspective (or oblique projection) view. The player attempts to deliver a week of daily newspapers to subscribing customers, attempts to vandalize non-subscribers' homes and must avoid hazards along the street. Subscribers are lost by missing a delivery or damaging a subscriber's house. If the player loses all of their lives, or runs out of subscribers, the game ends.
The game begins with a choice of difficulty levels: Easy Street, Middle Road and Hard Way. The object of the game is to perfectly deliver papers to subscribers for an entire week and avoid crashing (which counts as one of the player's lives) before the week ends. The game lasts for seven in-game days, Monday through Sunday.
Controlling the paperboy with the handlebar controls, the player attempts to deliver newspapers to subscribers. Each day begins by showing an overview of the street indicating subscribers and non-subscribers. Subscribers and non-subscribers' homes are also easy to discern in the level itself, with subscribers living in brightly colored houses, and non-subscribers living in dark houses.
The player scores points for each paper delivered successfully (either at a subscriber's doorstep or inside their mailbox, the latter of which awards more points), as well as breakage points by damaging the houses of non-subscribers. A perfect delivery (all subscribers get their papers, and none of their houses are damaged) results in all the points being worth double for that day, and an extra subscriber is added. At the end of each stage is a training course with various obstacles to throw papers at (which gives bonus points) and to jump over, and the player scores a bonus for finishing the course. Crashing on the course ends the round, but does not cost the player a life.
When a player fails to deliver a paper to a house, or damages a subscriber's house by breaking their windows, the resident will cancel their subscription, and the house turns dark. The player can regain subscribers by getting a perfect delivery, which adds one extra subscriber.