- Ability over Appearance: Word of God is that Rachael Leigh Cook was far too pretty to be an unpopular girl, and the idea that she needed a makeover was "implausible" - but he felt her performance was enough to make it believable.
- Awesome, Dear Boy: Kevin Pollak agreed to be in the movie because he liked Freddie Prinze Jr in The House of Yes and wanted to work with him.
- Creator Backlash: M. Night Shyamalan, while revealing that he ghostwrote the film, regretted his involvement in it.
- Dawson Casting:
- Rachael Leigh Cook was nineteen at the time, just barely averting the trope. Jodi Lyn O'Keefe was the same age. Anna Paquin likewise was sixteen.
- Played straight by Freddie Prinze Jr (22), Paul Walker (25), Gabrielle Union (26), Elden Henson (21), Lil' Kim (24), and Clea DuVall (22).
- Enforced Method Acting: The red dress was a little smaller than Rachael Leigh Cook's size, which helped convey that Laney is uncomfortable and unsure of herself wearing it. She actually had to hold her breath when doing the Grand Staircase Entrance.
- He Also Did: M. Night Shyamalan revealed in an interview with Movies.com that he did a ghost-write of this film.
- No Budget: To the extent that the outfits in the prom scene were mostly gotten from the Salvation Army.
- Playing Against Type: Jodi Lyn O'Keefe was known for Nash Bridges or Halloween H20: Twenty Years Later, playing down-to-earth good girls. She described the Alpha Bitch Taylor Vaughn as completely unlike anything she'd done before.
- Star-Making Role: This put Rachael Leigh Cook on the map in the late 90s...until the unfortunate failure of Josie and the Pussycats.
- Throw It In!: Kevin Pollack improvised most of the wrong answers to Jeopardy.
- Uncredited Role: M. Night Shyamalan was an uncredited script doctor for the screenplay. Shyamalan's contributions are mentioned on the DVD Commentary for the film - namely expanding Laney's relationship with her father, the performance art pieces and the famous "Am I a fucking bet?!" line.
- What Could Have Been: Test audiences couldn't understand why the prom dance scene was happening. It was then re-shot to add Usher in to link it.
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