Gangsters is played by alternating between turn-based and real time gameplay. At the beginning you give orders to the gangsters (or 'hoods') under your control, which are then played out in front of you during the real-time aspect of the game (the working week).

To have any chance of winning the game, you must begin expanding your territory by giving your hoods the order to extort businesses into paying protection money to you every week (which must be collected). You will also have to begin recruiting more hoods for your gang as soon as possible by giving your hoods the recruit order. Additional hoods can be recruited from gyms, pool halls, cafés, the docks and the unemployment office.

The hoods have many different attributes such as intelligence, fists, knives, etc. which make them suitable for different missions. A hood with high knife skill and low fists skill may inadvertently kill someone he was merely sent to beat up, for instance. Hoods can be promoted to lieutenant, which gives them the ability to lead teams of hoods. It is also possible to hire a lawyer and an accountant. There are different automobiles and weapons that can be purchased to aid in carrying out missions.