Hoodlum & Son (2003)

In 1933, ten-year-old Archie, full of mischief, is stuck with his distracted father, Charlie, who is a hesitant gangster owing money to the fearsome mob boss Benny “The Bomb” Palladino. Benny offers Charlie a final opportunity to settle his debt by retrieving money from a competitor. However, when Archie tags along and ends up in the rival gangster's speakeasy, a whirlwind of strange incidents ensues, forcing them to escape without the cash they were supposed to collect.