Hoodlum & Son is a 2003 comedy-crime film. In 1933, a mischievous ten year old, Archie (Myles Jeffrey), is left in the care of his unattentive father, Charlie (Ted King), a reluctant gangster indebted to mob boss Benny “The Bomb” Palladino (Robert Vaughn). 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.

Baker Dill is a fishing boat captain leading tours off a tranquil, tropical enclave called Plymouth Island. His quiet life is shattered, however, when his ex-wife Karen tracks him down with a desperate plea for help.