This is an "open-world" action game in which players assume the role of Vito Scaletta, an ex-convict and World War II veteran who becomes involved in a crime family. The game depicts a 1940s and 50s urban landscape, which includes a criminal underworld that the protagonist must navigate through in order to progress. Players complete various missions that either advance the main storyline or award the player with in-game currency and connections.
Many of the missions require players to engage in criminal activity: stealing cars, robbing gas stations, running drugs, killing rival gang members. Players use pistols, Tommy guns, shotguns, and knives to kill enemies and occasionally civilians. Blood often spurts out of injured characters, stains the walls/ground, and occasionally sprays onto the screen. Some cutscenes depict more intense instances of violence, including close-range executions, stabbing, and throat slitting. Within the free-roaming context (i.e., not missions), players have the ability to attack police officers and pedestrians on the streets, in bars, shops, etc; however, these acts are not directly rewarded, preventing players from maintaining a low profile from the police.
During the course of the game, players can encounter some sexually suggestive material: brothels with prostitutes in revealing lingerie; a gentleman's club with female dancers; and Playboy magazine pin-ups hidden in certain areas of the game (topless images, bare buttocks). There is also a gallery accessible from the main menu, where players can view all of their collected pin ups. One cutscene briefly depicts the top of a woman's head as she performs fellatio on a man—the camera cuts away to other patrons at the table, the man's reactions.
Alcohol and drug use are also depicted in the game. Players' character can order alcohol at a bar and drink until his vision becomes blurry; players are able to drive their cars in this impaired state. Characters are also depicted buying and selling drugs in a cutscene montage. Although the protagonist is never depicted using drugs, a few ancillary characters sometimes can be seen smoking marijuana or sampling cocaine. Language such as "f**k," "sh*t," and ""n**ger" can be heard in the dialogue.