Al Capone famously said, "You can get pretty far in life with a smile, but you can get a lot farther with a smile and a gun."

With a Smile & a Gun is a fist-clenching game of intrigue and sneakiness in which two criminal gang leaders fight over the domination of a city's underground businesses during a very noir Prohibition Era. They have to outthink their rival, send the police into their business, use their network's abilities, and decide when to lay low and when to go all-out.

Mechanically speaking, With a Smile & a Gun is a dice-drafting, area-majority game about taking the last 4 — not because you need it, but because your opponent does. Each round, thirteen dice are rolled in a pool. A player then drafts two dice: one for their movement around the city, which will place influence, and one for an action. After both players have drafted three times, a non-player character — one of five in the box — will use the leftover die for its own movement, affecting the game in its own way. The player who attracted the least attention, that is, who has lowest sum of action dice, takes a special scheming action, then majorities will be scored for each district.

After three rounds, the player with the most points wins.