Uptown Girls (2003) iCAPx3

In New York City, Molly Gunn is a spoiled, wealthy, immature young woman who lives as if she were a fairytale princess. Her father, a popular rock guitarist, died in a plane crash with her mother when she was little. In a nightclub on her birthday she meets Lorraine "Ray" Schleine, a nasty young girl with an adult attitude, who lives with her careless mother and a terminally-ill father in a fancy uptown apartment. When Molly's accountant vanishes with her US$ 100,000,000.00 inheritance, she is left with nothing but debts and must work to survive--with no previous experience or marketable skills. She is hired to be Ray's babysitter, and their close contact makes Molly reach maturity and Ray act like the 8-year-old she is.