Trivia: The publishing house where Bridget works is called "Pemberley Press". For those who haven't read or seen "Pride And Prejudice", this is also the name of Mr. Darcy's estate.
Trivia: In the scene where Simon (Laney's brother) is rollerblading in the cafeteria, with a pepper grinder, he stops at a table and takes a tray from a pretty girl. If you look closely, that girl is Sarah Michelle Gellar.
Trivia: Polly explains to Reuben that she's travelled to many exotic places (Singapore, Costa Rica, etc.). The last place that she lists is Buffalo, New York, which is the city that Jennifer Aniston's (Polly) last movie, Bruce Almighty (2003), took place in.
Trivia: The film's soundtrack album knocked Michael Jackson's "Thriller" off the top of the U.S. album charts, where it had ranked for more than a year.
Trivia: Nicole Kidman played all her own piano for this movie.
Trivia: At the prom, the popular girls tell a couple that there's "no room" at their table. The couple is dressed like Mary and Joseph of the Bible, whom were told there was "no room" at the inn (and therefore had to give birth to Jesus in a stable).
Trivia: Due to the political situation in Iraq, the location for scale shots was moved from Morocco to Mexico, an ideal alternate choice with its broad beach. However, the rushed decision presented some obstacles. Coastal Mexico is an endangered turtle habitat, so to be granted permission to set up the Greek encampment and build boats on the large stretch of beach, the film crew implemented their own turtle incubation nursery, releasing a multitude of turtles while on location in Mexico. They also did not have an accurate idea of the physical conditions of that particular beach - it was unstable and 100 feet of beach washed away overnight, leaving Greek ships teetering precariously on the edge of the bank with the missing sand.
Trivia: The picture of Billy that Eric is using to monitor Billy's progress from grade to grade is the same headshot photo that was used in Happy Gilmore for the signboards some people were carrying in the crowds.
Trivia: In one of the letters that Gerry sends Holly about choosing a future career he says "and there's no such thing as a Vampire Slayer". Funny statement since one of the stars of the film is James Marsters, who is famous for his role as Spike in Buffy the Vampire Slayer.
Trivia: The painting of Jeremy that Todd Cleary ('Keir O'Donnell') creates and gives to Jeremy was kept by Vaughn after filming.
Trivia: Orchard house, the house in the movie, is actually the house that Little Women's author, Louisa May Alcott was raised in.
Trivia: When the film was shown during the 2003 Baseball Hall of Fame ceremony, Susan Sarandon and her partner Tim Robbins were not invited because of the controversy surrounding their anti-war views on Iraq.
Trivia: Writer/director Amy Heckerling was in the middle of writing the script when she saw Alicia Silverstone in an Aerosmith video on MTV, and immediately knew that was who she wanted to play Cher.
Trivia: In the 40th anniversary re-mastered edition they have used Audrey Hepburn's original singing track for the "Wouldn't it be lovely" song.