Beginning in 1974 and then quickly fast forwarding to 1985, the movie chronicles the coming of age of three boyhood friends in the violent, mafia-controlled streets of Brooklyn. When one becomes enamored with the mafia lifestyle, all three friends are placed in grave danger as relationships and lives are threatened.
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 with 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 fiancee. 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 mobster who controls their Brooklyn neighborhood, Michael and Bobby are drawn into that world despite their reluctance to get involved.