The game follows a character called 'Joey Bane' whose nickname is decided by the player e.g. Joey 'Scarface' Bane. The character's father is murdered at the beginning by a mob controlling most of New Temperance (the fictional state where the games are set), the leader of the mob is Frankie 'Hammer' Constantine. The player progresses through the game by defeating different gangs and gang leaders that are all connected to the killing of Joey Bane's Father.
The game is very heavily a strategy game, utilizing a point and click interface. Each gangster ('hood') the player controls can have four subordinates that will help the character in a firefight. Players can use vehicles to reach targets faster, attempt drive-bys and transport goods. Weapons can be upgraded, including those of your 'hoods'. Business must be bought, sold and taken over from rival gangs, players must set up many types of illegal businesses to make the most money e.g. gambling dens, breweries and brothels.
The player is given objectives to fulfill. They range from setting up illegal businesses, claiming the enemies' business, kidnapping, and murder.