- Accidental Aesop: While one wouldn't expect one from a low-brow parody movie, watching the plot can give the moral "There's no point in waiting for "the perfect moment", to the exclusion of all else. Even if such a moment does come along, chances are someone else will take advantage of it before you can."
- Awesome Music:
- The cover of "Tainted Love" by Marilyn Manson.
- Also the cover to "Don't You Forget About Me" by Sprung Monkey. You wouldn't expect to hear such passion in a song for a spoof movie.
- The rest of the soundtrack counts, as it's full of '80s covers from bands such as The Smashing Pumpkins ("Never Let Me Down Again" by Depeche Mode), Orgy ("Blue Monday" by New Order—the cover was a radio hit a couple of years prior to this film), System of a Down ("The Metro" by Berlin—the cover was previously featured on the soundtrack to Dracula 2000), Saliva ("Message of Love" by Pretenders) and Muse ("Please, Please, Please Let Me Get What I Want" by The Smiths).
- Best Known for the Fanservice: Areola, the girl who appears naked in all her screentime. Oh, and Chris Evans in a whipped cream bikini... with a banana near his posterior.
- Big-Lipped Alligator Moment: The other Token Black Guy. He is one of the few gag characters not to appear again. That being said, the movie already had a Token Black Guy.
- Crosses the Line Twice:
- The White WASPs performing what is definitely not their Black opponents' cheer... which identifies them as their opponent, boasts that they are definitely not white, and includes the line "Break it down, niggas!"
- Reggie Ray getting hit with his last concussion would normally be Dude, Not Funny!, but having it happen by Jake's hail Mary pass go way off course into his head and the stretcher breaking under his weight exacerbating said injury makes it circle back into hilarious.
- Harsher in Hindsight:
- In a parody of 10 Things I Hate About You, Jake tries serenading Janey with "Janie's Got a Gun", and it predictably goes wrong. Nowadays, this seems more inappropriate, given the decade that followed had enough school shootings to force certain facilities to install metal detectors.
- Depending how you view it, the character Reggie Ray (The Fat Guy), regarding his weight and especially health (particularly the Running Gag about his concussions) can either now be looked at as cringe-worthy or worse than before now that Ron Lester has passed on. Also just in general, because of it parodies how little sports programs cared about concussion. It took until the mid-2010s before it started being taken as the very serious, long term problem that it is.
- Heartwarming Moments:
- When Janey's brother accuses her of acting like a lesbian, their father tells them that "if Janey wants to be a rugmuncher, that's her decision". He may be The Alcoholic, but damn if he isn't supportive — when he remembers, anyway. This became even more Heartwarming in Hindsight in 2020 when Chyler Leigh came out.
- When the Siamese twins are crowned prom queen, Janey gives them the warmest smile.
- Amidst the insanity of the rest of the film, Good Charlotte performs a very sincere, very sweet cover of "Put Your Head(s) On My Shoulder."
- Hilarious in Hindsight:
- Pretty much everything about Jake since his actor is now world famous for playing Captain America, one of the most straight-laced characters in fiction.
- There is a banana in America's ass.
- Captain America dated Supergirl's sister.
- Molly Ringwald saying that masturbation is healthy.
- We'd later get two more Yellow Rangers to take their clothes off.
- The teen movie genre swiftly dried up shortly after the release of this film, making its title even funnier.
- Three years before Mean Girls, Lacey Chabert played one of a three-girl, pink-wearing clique, following a blonde Alpha Bitch.
- In one scene, Janey's brother accuses of her being a lesbian. Janey's actress Chyler Leigh would later play openly lesbian Alex Danvers in Supergirl (2015), fourteen years after the film came out. Even funnier, Chyler Leigh came out as LGBTQ in 2020.
- The extremely Les Yay-tastic makeover scene with Catherine and Jenny also, when you consider not only Chyler's performance as Alex but also Mia Kirshner going on to have a lead role in The L Word for several years.
- The amount of No Yay between Jake and his sister Catherine, considering Freddie Prinze Jr. and Sarah Michelle Gellar married just one year later.
- Pretty much everything about Jake since his actor is now world famous for playing Captain America, one of the most straight-laced characters in fiction.
- Hollywood Homely: Parodied; when looking for a girl to turn into Prom Queen for their bet, Jake and Austin make the claim that Chyler Leigh in glasses, a ponytail, and messy overalls is uglier than a variety of other girls with intentionally exaggerated physical flaws.
- Les Yay: During Janey's makeover scene, Catherine pokes her nipples and gropes her breasts. Janey makes no effort to get away from her, and the noises she makes sound like she can't quite make up her mind whether she's enjoying it or not.
- Nausea Fuel:
- The girl-on-girl kiss. To be more specific, a sloppy girl-on-girl between Catherine and a much, much older lady.
- There's also the scene where a girl takes a very long and loud dump that nearly floods a classroom.
- Janey gets caught masturbating with a very large vibrator by her father, brother, a catholic priest and several orphans.
- Jake's groupies throw him their underwear. One of them just so happens to be a guy who throws him a jockstrap.
- Jake sticking a banana up his rectum.
- Catherine talking about her sex life is this in-universe to everyone except Ox.
- Nightmare Fuel: Marty’s death scene in a flashback.
- One-Scene Wonder:
- The wise janitor... played by Mr. T!
- Molly Ringwald as the flight attendant who tears apart Jake's romantic speeches to Janey.
- Paul Gleason reprises his role as Richard Vernon when Mitch and his friends are put in detention.
- The unseen kid in the poetry reading scene for his Brutal Honesty.
- Retroactive Recognition:
- Jake is Johnny Storm! And Captain America! (this was actually Chris Evans' first major role).
- Why the hell does Private Hirschberg think he's Asian? And since when was he buddies with Jimmy Olsen and Mimi-Siku?
- Mandy apparently wasn't much better in high school...though maybe she did improve after marrying Sarek.
- Anna Stern was one of the conjoined twins.
- Ah, so that's what Ted Mosby was like in high school.
- The "Ferris Bueller"-type party thrower gained some facial hair and the ability to see the future, and now writes about Sam and Dean Winchester's Supernatural adventures.
- Janey went on to be Dr. Lexie Grey and Alexandra "Alex" Danvers.
- Jaime Pressly was a bitch in this movie. Not that her most current role did any more justice to her, that is.
- Never knew that Marty Deeks was such an asshole.
- H. Jon Benjamin is the football trainer, rather than a superspy or restaurant owner.
- Vindicated by History: It took a critical beatdown when it first came out, but after the increasing number of shallow parodies took over the genre in the mid/late-2000s, viewers have come to appreciate that NATM was making a sincere effort to be both funny and faithful to the genre and tropes it was skewering.
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