Mary Kay Letourneau: All American Girl (2000)

Mary Kay Letourneau is a teacher, who is married and has children. She then has an affair with one of her students who is underaged. When she gets pregnant, she is charged with statutory rape. After pleading with the judge to give her a chance, she was instructed not to see the boy again, but when she not only disregards the instructions, she gets pregnant again. She is sent to prison.