In 1965, Boston teenager Michael Dunn (Andrew McCarthy) and his young sister Boo (Jennifer Dundas) have been sent to Brooklyn to live with their Irish-Catholic grandparents (Kate Reid & Richard Hamilton (actor)) following the deaths of their parents. He is enrolled at St. Basil's, the strict all-boys Roman Catholic school run by St. Basil's Church, where his grandmother is determined to see him fulfill his parents' dream of him joining the priesthood after graduation. Dunn befriends Caesar (Malcolm Danare), an over-weight, bespectacled bookworm. Caesar helps Dunn catch up with the rest of the class, but because of their association, foul-mouthed class bully and underachiever Ed Rooney (Kevin Dillon) bullies Dunn with a prank outside of the soda fountain across the street from school.
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