I still play Gangsters: Organized Crime often, the game was released in 99... Yet nothing has matched its nostalgic fun, unfortunately the sequel was terrible. I'll admit that the game has plenty of flaws but again no developer has even matched its depth. Though there were a few similar releases but the pretty graphics didnt compensate for the terrible quality in terms of gameplay and style.

edit: Game is complex and requires plenty of patience, I recommend if you're interested. Prohibition mafia fun!