Ensemble Dark Horse: 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".
Nightmare Fuel: The scene where Kelly beats up Matthew comes right out of nowhere. For a comedy film, this is quite intense.
A blonde Olivia Wilde has a small role as a high school student.
Real Life porn actress Samantha Ryan appears next to Olivia Wilde in the opening montage.
Sunny Leone has a small role during a party, years before becoming famous in Bollywood.
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.
Unintentional Period Piece: The bombshell that Danielle is actually a porn star gets dropped when Eli has to search around to find a film on video tape; ten years later a quick Google search could have told him as much. The movie they shoot in the climax is also distributed on VHS as opposed to DVD (or they could even distribute digitally). Danielle's porn star alias is 'Athena' and she has friends called April and Ferrari; porn stars going by a single name was very common around the time the film was made but had fallen out of popularity by the next decade in favor of the standard first and last that had been common previously.
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.