Dual teen comedies coming out within a year of one another trying to capitalize off of the success of American Pie and that weird Shakespeare trend that happened in the late 90's. Get Over It incorporates Midsummer Night's Dream while Whatever It Takes does a Cyrano DeBergerac thing. But most importantly the casts: James Franco, Kirsten Dunst, Mila Kunis, Martin Short, Shane West (in both), Colin Hanks (in both), Aaron Paul, Ben Foster, Sisqo, Vitamin C, Coolio.
"trying to capitalize off of the success of American Pie"
These two quality, light comedies don't have much to do with American Pie (1999). They're much more in this tradition:
Clueless (1995) Wish Upon A Star (1996) Trojan War (1997) Can't Hardly Wait (1998) 10 Things I Hate About You (1999) Drop Dead Gorgeous (1999) Never Been Kissed (1999) She's All That (1999) Bring It On (2000) Down To You (2000) The Hot Chick (2002) Orange County (2002) She Gets What She Wants (2002) Bring It On Again (2004) Mean Girls (2004) It's A Boy Girl Thing (2006) John Tucker Must Die (2006) She's The Man (2006)
F'ing Åmål / Show Me Love (1998) Dancer, Texas Pop. 81 (1998) Drive Me Crazy (1999) Varsity Blues (1999) Jawbreaker (1999) Election (1999) Boys and Girls (2000) Not Another Teen Movie (2001) Sugar & Spice (2001) Slap Her, She's French! (2002) ... I see, you got the AKA Cheats (2002) The New Guy (2002) Freaky Friday (2003) How to Deal (2003) Sleepover (2004) Confessions of a Teenage Drama Queen (2004) The Perfect Score (2004) Pretty Persuasion (2005) Bring It On: All or Nothing (2006) Superbad (2007) ... and with that one a new era begins
Clueless (1995) Wish Upon A Star (1996) Trojan War (1997) Can't Hardly Wait (1998) Dancer, Texas Pop. 81 (1998) Show Me Love (1998) 10 Things I Hate About You (1999) Drive Me Crazy (1999) Drop Dead Gorgeous (1999) Election (1999) Jawbreaker (1999) Never Been Kissed (1999) She's All That (1999) Varsity Blues (1999) Boys and Girls (2000) Bring It On (2000) Down To You (2000) Whatever It Takes (2000) Get Over It (2001) Not Another Teen Movie (2001) (loved it but I'd put it in the American Pie category) Sugar & Spice (2001) Cheats (2002) The Hot Chick (2002) The New Guy (2002) Orange County (2002) She Gets What She Wants (2002) Freaky Friday (2003) How to Deal (2003) Bring It On Again (2004) Confessions of a Teenage Drama Queen (2004) Mean Girls (2004) The Perfect Score (2004) Sleepover (2004) Pretty Persuasion (2005) It's A Boy Girl Thing (2006) John Tucker Must Die (2006) She's The Man (2006) Bring It On: All or Nothing (2006) Superbad (2007)
We could add My Date With The President's Daughter (1998) Rushmore (1998) Cruel Intentions 2 (2000) The Princess Diaries (2001) Pumpkin (2002) Agent Cody Banks (2003) D.E.B.S. (2004) The Girl Next Door (2004) Monster Island (2004) Napoleon Dynamite (2004) Saved! (2004) Sky High (2005) High School Musical (2006) The Sasquatch Gang (2006) Stick It (2006) Take The Lead (2006)
Given your policy "quality, light comedies" I tried to avoid action, crime and horror themed movies like Agent Cody Banks or Monster Island on my list, but also college settings to not define it down to the American Pie category – which IMO applies to Cruel Intentions 2 by far more than to Not Another Teen Movie ;) I think the latter had a pretty close connection to Whatever It Takes, which started this all, and even more to She's All That, which is a prominent representative named by yourself. It's also mocking a good amount of the named movies.
Actually I had some of your extensions on my list initially, but removed them again, Saved! being one of them. But now, weeks later, I can't even remember the exact reason! :D – Any idea? Maybe it was just accidentally, maybe it was because I thought it to be too problematic with religion, sexual disorientation, pregnancy and such ... I don't know.
Some of your additions like My Date with the President's Daughter, The Princess Diaries or The Girl Next Door also focus too much on a single (or a pair of) main character(s) as opposed to a (at least attached) group of students, which I also excluded after rethinking the subject. I know it's difficult to draw a line there, but I tried. And High School Musical, come on ... this spawned an entirely different genre, eventually leading us to the Step Up franchise in the worst case ^^
Too bad no one else finds this worthy of discussion, that might help alot.
Not Another Teen Movie is a great comedy, but when not edited for TV, the genuinely strong toilet and sexual humor (and both of those combined, more than once) takes it out of the Whatever It Takes world imo. They're actually supposed to be younger in Cruel Intentions 2 than in Cruel Intentions IIRC, but in any case I think you're on to something that they're on the periphery too.
I put Saved! in and then took it out the first time too. Yeah it touches on some serious issues so I think it might depend on mood while watching it or even mood while remembering it. I think how "funny" the camp stuff in both the Cruel Intentions is would depend on mood, too. I don't know if you've seen Monster Island but it is largely a generic -- I mean "generic" as a compliment in our context -- ensemble-cast-oriented John-Hughes-high-school-kids-bickering-with-each-other-and-getting-interested-in-each-other comedy. Set on, admittedly, a monster island.
I thought High School Musical was funny, in addition to just generally pleasant. I love music, and I thought Grabeel and Tisdale nailed the musical jokes.
Before I'd ban Not Another Teen Movie from the list, despite its connections and references, just because of some questionable scenes I can't even remember quite well, I'd ban this distinct genre all day! It's not a value judgment, just differentiation from the originally discussed movies.
Alright then, so as far as I am concerned it's now up to someone else to chime in ~~~