New York, 1974: three kids find a body in a car, the victim of a Mob hit. Eleven years on, against the backdrop of a Mafia war, the childhood pals make choices that jeopardise not only their friendship, but also their lives, as Carmine starts an apprenticeship with Mob boss Caesar.

In 1985 Michael (Freddie Prinze Jr.), the narrator, is a lovable charmer with the soul of a con man who successfully scams his way into the pre-law program at Columbia University. In contrast to Michael’s desire to leave the Brooklyn streets behind, his close friend Carmine (Scott Caan) is a handsome lady-killer who is enamored of the Mafia lifestyle and wants only to stay there. Rounding out the trio is Bobby (Jerry Ferrara), an endearing cheapskate who longs for a simple life of working at the Post Office and settling down with his fiancée. While at Columbia, Michael falls for a beautiful young student named Ellen (Mena Suvari), a society girl whom he initially wins over with his preppy schoolboy cover. As their relationship blossoms, leaving the streets behind seems increasingly possible, but when Carmine catches the eye of Caesar (Alec Baldwin), a feared Gambino family capo who controls their neighborhood, Michael and Bobby are drawn into that world despite their reluctance to get involved.

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