First Appeared: Grand Theft Auto: Vice City (2002)
Founding Father: Rockstar North
Notable Residents: Las Cabrones, the Haitians, Colonel Cortez, the Vercetti Crime Family

As the number of shirts and afghans and cars that are painted with his face can attest to, Scarface has touched the hearts of the world, making this video game a no-brainer. Rockstar really hit it out of the park when they combined that shining citizen with their groundbreaking GTA series. Vice City has everything—the affluent beaches, a glitzy downtown, the slums, the parks, islands that open up the more involved you become in the syndicate. Driving around Vice City, listening to your all-'80s playlist, it's hard not to want to awkwardly (but forcefully) woo Michelle Pheiffer and fall asleep on a pile of coke.