Watch FilmoFlix. Bringing Up Bobby is the story of a European con-artist and her son Bobby, who find themselves in Oklahoma in an effort to escape her past and build a better future. Olive and Bobby blithely charm their way from one adventure to another until Olive's criminal past catches up with her. Consequently, she must make a choice: continue with a life of crime or leave the person she loves most in an effort to give Bobby a proper chance in life.