Longfellow Deeds (Adam Sandler) is content to run his pizzeria in the cozy New Hampshire hamlet of Mandrake Falls. His only further desire is to someday see one of his corny rhymes printed in a greeting card. Deeds is awarded much more when he inherits the $40 billion empire of a media tycoon, a distant relative. He is lured to New York City by unscrupulous partners of the deceased where he is preyed upon by greedy stockholders. He also makes ample fodder for tabloid journalists, notably reporter Babe Bennett (Winona Ryder) who poses as a school nurse from Iowa to win Deed's heart and expose him as an idiot to her viewers. Against her will and her own sleazy principles, Babe falls for the charming naivety of Deeds, whose fortune is in jeopardy.