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You can stream Hoodlum & Son (2003) on Amazon Prime with a subscription.

In 1933, a mischievous ten year old, Archie, is left in the care of his unattentive father, Charlie, a reluctant gangster indebted to mob boss Benny “The Bomb” Palladino. Benny gives Charlie a last chance to clear his ‘debt’ by collecting money from a rival, but when Archie follows his father into a rival gangster’s speakeasy, a series of bizarre events take place culminating in them fleeing without the money.