Best Known for the Fanservice: Elisha Cuthbert plays a porn star, which is by far the most remembered part of the movie. Of course it's a huge plot point as well but still.
Ensemble Darkhorse: Kelly for being played by Timothy Olyphant in a hilarious performance. The crowner is the scene where he bursts into one of Matthew's classes and drags him out - before saying to the class "stay in school".
It Was His Sled: It's actually a while before Danielle is revealed to be a porn star in the film, but all the trailers spoiled it. And everyone knows that she's a porn star these days.
Nightmare Fuel: The scene where Kelly beats up Matthew comes right out of nowhere. For a comedy film, this is quite intense.
The Scrappy: Jeannie from the bank, for setting up the third act conflict through sheer idiocy. She hands over all the money to Kelly, assuming he's Mr Salinger, and then threatens Matthew with being arrested when she finds out the truth. The thing is - she is entirely at fault. She didn't bother to check ID or make sure who she was handing the money over to. Matthew committed no fraud - he could easily say he was being threatened by Kelly (which he was). Jeannie is entirely at fault, accepts no responsibility and leaves a bunch of teenagers to clean up the mess she made.
Signature Scene: Matthew watching Danielle undress from his bedroom window and then getting caught for it. It was even parodied in Paris Hilton's music video for "Nothing In This World".
The Jerk Jock characters freely say the word 'fag' a couple of times. While it's used to show them as jerkasses, it likely wouldn't be said so freely in today's homophobia awareness society.
Subverted when it comes to Matthew's initial voyeurism towards Danielle. He watches her change but she catches him and while it's Played for Laughs, it's still illustrated that spying on her is not okay.
What Do You Mean, It's for Kids?: Well not for kids but for teens. A few critics were shocked that it was marketed as such. It even won a Teen Choice Award as 'Choice Movie: Your Parents Didn't Want You To See'.
The Woobie: Once you get to know Danielle, you see how deeply she's hurting. She's clearly heartbroken when Matthew finds out she was in porn. The "so this is what you think of me" line is a real Tear Jerker.
Fan Disservice : When Meg's clothes come off, it's humiliating and cringe-worthy.
Fridge Brilliance : A lot of the discomfort in reading the novel comes from David's inertia. It's very frustrating when no one moves to save Meg, instead standing around and watching. After a while, you start to realize that's exactly what you're doing as a reader. A gentle sort of Take That, Audience!.