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Kate and her actor brother live in N.Y. in the 21st Century. Her ex-boy friend, Stuart, lives above her apartment and finds this space near the Brooklyn Bridge where there is a gap in time. He goes back to the eighteen hundreds and takes pictures of the place. Leopold, a man living in the 1870’s, was puzzled by Stuart’s tiny camera and decides to follow him and they both ended up in this century. Leopold is clueless about his new surroundings. He gets help and insights from Charlie who thinks that Leopold is an actor who is always in character. Leopold is a highly intelligent man and tries his best to learn and even improve the modern conveniences that he encounters.

Billy Madison is a non-working, non-educated slacker who lives entirely off his dad. He spends his day drinking beer, reading girly magazines, and hanging out by the pool. When his father realizes that Billy is unfit to run the family business, Billy decides that he must go back to school and earn a real education. He figures it will be no problem going back to high school and learning over again, until he learns that his father bought Billy’s passing grades all the way back in elementary school. Thus, Billy must return to elementary school and pass each grade one at a time in a short time, or else he loses his place as heir to the company. In addition, Billy tries to win the hand of Veronica, a sexy school teacher who thinks her students are more mature than Billy.

Frank is a retired Lt Col in the US army. He’s blind and impossible to get along with. Charlie is at school and is looking forward to going to university; to help pay for a trip home for Christmas, he agrees to look after Frank over thanksgiving. Frank’s niece says this will be easy money, but she didn’t reckon on Frank spending his thanksgiving in New York.