Awesome, Dear Boy: Rosie O'Donnell loved the book as a kid, so when she found out it was being made into a movie, she was ecstatic, and when she was asked to play Ole Golly she immediately said yes without even reading the script.
Colbert Bump: Michelle Trachtenberg has said that many now grown up 90s and 2000s children have told her that they were inspired to become writers after seeing the film.
Dawson Casting: Actually averted in the movie; Michelle Trachtenberg was the same age as Harriet. She turned ten on the first day of shooting.
Fake American: Gregory Smith (Sport), Charlotte Sullivan (Marion), Dov Tiefenbach (The Boy with Purple Socks), Alisha Morrison (Laura Peters), Jackie Richardson (Janie's mother) and of course Robert Joy were all Canadians.
Life Imitates Art: Michelle Trachtenberg herself eventually became a writer in her adult years.