Organized crime, gangsters and evil in general

Despite the real-world connotations, organized crime always fascinated gamers. Wether you're a mafia boss, a detective in the 20's in Chicago, a car thief tied to organized crime, if the game is good, we're all going to play it and have fun despite the gangster theme.

Most popular organized crime, gangsters games

Grand Theft Auto

action-adventureDOS, Windows XP/98/95

Grand Theft Auto 2

action-adventureWindows XP/98/95

Dope Wars

simulationWindows XP/98/95

Organized crime, gangsters games

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Capone

DOS19883.8/5 Actionware Corporation
Chicago 90

DOS19893.8/5 Microids
Deja Vu 2: Lost in Las Vegas

DOS19904.1/5 ICOM Simulations
Deja Vu: A Nightmare Comes True

DOS19874/5 ICOM Simulations
Dick Tracy

DOS19903.3/5 Titus Interactive
Dime City

DOS1995NSFW4/5 Cyberdyne Systems
Dope Wars

Windows XP/98/9519984.2/5 Beermat Software
Drug wars: a game based on the New York drug market

DOS19843.2/5
Grand Theft Auto

DOSWindows XP/98/9519974.1/5 DMA Design

In Grand Theft Auto the player takes the role of a criminal who can freely roam around the city (Liberty City) completing tasks for the local mobs: stealing cars, killing pedestrians, all of it while avoiding the police and the army. The freedom of gameplay and the "I'm the bad guy" appeal of the game made the Grand Theft Auto series very popular.
Grand Theft Auto 2

Windows XP/98/9519994.2/5 DMA Design

Grand Theft Auto 2 is the second chapter in the successful Grand Theft Auto series. GTA 2 is an abandoned top-down action-adventure / driving hybrid game developed by DMA Design and released by Rockstar Games in 1999 for Windows. In GTA 2 you are a wannabe criminal roaming the streets of a fictional city, stealing and driving vehicles while escapin...
Guns 'R' Us

DOS19933.8/5 Future Vision
King of Chicago

DOSMac19873.2/5 Cinemaware
The Godfather

DOS19913.3/5 Creative Materials
The Untouchables

DOS19893.9/5 Ocean Software