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You can stream Wiseguy (1987) on Amazon Prime with a subscription.

Vinnie Terranova does time in a New Jersey penitentiary to set up his undercover role as an agent for the OCB (Organized Crime Bureau) of the United States. His roots in a traditional Italian city neighborhood form the underlying dramatic base throughout the series, bringing him into conflict with his conservative mother and other family members while acting undercover as syndicate enforcer.

Vinnie Terranova risks losing his soul while infiltrating the very criminal underworld he is sworn to dismantle. This undercover operation pits his deep-seated Italian heritage against the brutal, isolating reality of life behind bars.