Unlike his brother Sid, Tom receives "lickings" from his Aunt Polly; ever the mischief-maker, would rather play hooky than attend school and often sneaks out his bedroom window at night to adventure with his friend, Huckleberry Finn the town's social outcast. Tom, despite his dread of schooling, is extremely clever and would normally get away with his pranks if Sid were not such a "tattle-tale."
As punishment for skipping school to go swimming, Aunt Polly assigns Tom the chore of whitewashing the fence surrounding the house. In a brilliant scheme, Tom is able to con the neighborhood boys into completing the chore for him, managing to convince them of the joys of whitewashing. At school, Tom is equally as flamboyant, and attracts attention by chasing other boys, yelling, and running around. With his usual antics, Tom attempts to catch the eye of Becky Thatcher, a new girl in town, and persuades her to get "engaged" by kissing him. But their romance collapses when she learns Tom has been "engaged" previously to Amy Lawrence. Shortly after Becky shuns him, he accompanies Huckleberry Finn to the graveyard at night, where they witness the murder of Dr. Robinson.