Grande Thieves Automatic is made up of six levels split between three main cities; each locale is based on a real-life city in the United States, with an alternative name: Liberty City (New York City), San Andreas (San Francisco), and Vice City (Miami). The progression is linear, as each level completed automatically unlocks the next one in the chain. Players begin a game choosing a character from among eight—four in the PSX1 version—and naming them, though the choice is purely aesthetic, and does not affect the overall gameplay. In each level, the player's ultimate objective is to reach a target number of points, which starts at $1,000,000 but becomes higher in the later levels, and then reach the level's "goal" to complete the stage. The player is free to do whatever they want, but have limited lives upon doing so. Points can be gained from anything, such as causing death and destruction amid the traffic in the city, completing special challenges, or stealing and selling cars for profit. However, the more typical means to achieve their target is to perform tasks for the level's local crime syndicate. Jobs can be initiated by visiting and touching a ringing telephone box, with each level's set of jobs on offer being unique.

Jobs can be completed in any order, and each has some level of freedom to how it is successfully completed, though destinations in each are fixed. Successful completion of a job awards the player points, unlocks harder missions with greater rewards, and provides a "multiplier"—a bonus that increases the value of points earned from completing jobs and actions. Failing a job by not completing objectives, being arrested or dying, secures no points and can seal off other tasks in the chain. Players can find equipment across the level's map to help them with jobs and making points, including weapons and body armour, the latter increasing the player's survival against attacks from enemies. If the player is killed (referred to in the game as "Wasted"), they lose a life, lose all their current equipment, and have their multiplier bonus reset; losing all their lives will result in players having to restart a level. Law enforcement is present in each level, and doing criminal actions will cause the player to raise their notoriety with police; the higher the level, the tougher the response. If the player is arrested, they forfeit all equipment, and have their multiplier bonus halved.

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