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If lampshading is your thing, boy, is this the movie for you.

  • Most notably, the Token Black Guy endlessly lampshading his own role makes for some of the best bits in the movie.
  • Jake goes into Janey's basement to comfort her after she runs out of the party crying gives us this exchange.
    Janey: How did you get in here? I deadbolted the door.
    Jake: There's a hole in the side of your house.
  • Molly Ringwald's cameo near the end, where she stops the movie dead in its tracks just so she can call out Jake for ripping off his Love Confession speech from other movies.
    Molly: Please tell me you didn't just quote Freddie Prinze Jr.
    Janey:...I knew it! That was a line from She's All That! I masturbate to that movie!
    Jake: Uh, do you mind?
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  • During the football game at the end, there's a "REGGIE RAY CONCUSSIONS LEFT" counter.
  • "Here at John Hughes, there are no cliques. There are no social groups. You're accepted for who you are, not for who you hang out with. Okay, we're gonna divide the tour into several smaller groups so you can get to know your peers a little more. Let's get all you big jocky guys over here in one group. Aaaaand get you slutty girls over here by me. Hey, how you doin'? Welcome! And uh, you losers should hang out in the back. Hey. HEY, that clearly includes you. Come on. Get back there. Take a good look at the kid standing beside you. They're your only friends for the next four years!"
    • The best part is that this predated a similar Long List gag in Mean Girls by a couple of years.
  • The blissful Brutal Honesty of Janey's dad is always worth a few chuckles.
    Mr. Briggs: Hey, I might be late to pick you guys up.
    Janey: Why, do you have a job interview today, Daddy?
    Mr. Briggs: No, honey, I'll probably just be way too drunk.
    Janey: That's good. We don't want you drinking and driving.
    Janey: (Beat) Okay. Bye, Daddy!
  • Catherine gives Janey the Beautiful All Along makeover by taking off her glasses and undoing her ponytail. And... that's it.
    • Followed by her slow-motion walk down the stairs to Sixpence None The Richer's "Kiss Me" which is promptly ruined by the stairs collapsing.
    Mr. Briggs: C'mon outta there, honey. Quit fartin' around.
  • And the scene where Janey is chosen for this treatment, beating out the cojoined twins, the albino hippie and the hunchback in terms of ugliness.
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  • The cheerleader who looks straight out of the 1950s... until her Tourette's syndrome kicks in.
  • Paul Gleason reprising his principal role from The Breakfast Club, with the cussiness turned Up to Eleven.
    Principal Vernon: Cry me a river, dickface!
    • And the Overly Long Gag where he keeps handing out detentions for talking back, to the point that it becomes his asking some long question to set up for a single-word response.
      Principal Vernon: You had enough yet?
      Mitch: No!
      Vernon: That's another one.
      Mitch: So?
      Vernon: You just say the word, I'll keep going.
      Mitch: Go!
      Vernon: Eenie, meenie, miney...
      Mitch: Mo!
      Vernon: Your Mother was a...
      Mitch: Ho!
      Vernon: He was a famous clown.
      Mitch: Bobo!
      Ox: Mitch, cut it out!
      • At which point Vernon starts giving him detention, and thoroughly confusing everyone as to who he's punishing when in the process.
  • The guy who keeps starting the Slow Clap at really, really inappropriate moments.
  • The entirety of "Prom Tonight", as it's a musical number that has no buildup to it, and contains some laughably inappropriate lines.
    Mitch: I'm getting pussy no matter what!
    Bruce: Even if it with dirty slut!
    Ox: True love is what I want the most!
    Chef: I just jerked off in your french toast!
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  • At the prom: "It's funny, isn't it? You'd never guess that everyone at this school is a professional dancer."
  • When Jake first takes the She's All That bet, this is the masterful approach he first uses on Janey:
    Jake: So listen, you ever wanna be the most popular girl in school?
    Janey: You mean... anorexic, superficial, a bitch, a whore who lacks any long-term goals?
    Jake: Exactly. if you're interested, I thought maybe you & me could go out sometime. Be seen in public together.
    Janey: You haven't spoken to me in like four years, Jake.
  • A non-lampshading example: When Jake punches out the plastic bag. "I don't know what that was for."
  • The all white WASPs' cheerleaders denying that they stole the all black Wildcats' routine, before breaking out into it word-for-word. Which includes them 'calling' themselves the Wildcats, saying that they (again, an all white cheer squad) are black and 'definitely ain't white'.
  • At one Wild Teen Party, another girl sees Areola and complains that they're wearing the exact same outfit. Both of them are naked.
  • Jake's Brutal Honesty when he decides not to get together with Janey at the end of the movie, reasoning that they wouldn't see each other often, he'd get drunk and have a one night stand, then she'd get angry after finding another girl's underwear in his room.
  • Malik meets another Token Black Guy at the party, and convinces him to leave.
  • When an English teacher berates his class for having such a low-brow sense of humour, interspersed with a scene where a girl is taking a loud shit. It climaxes with the floor giving out from under her, landing in his classroom and several gallons of shit being sprayed in his direction. Topped off with a fart and the girl sheepishly excusing herself.
    • This is then followed by a lunchroom scene where the same girl receives a heap of nasty sludge on her plate, explaining how the aforementioned scene could have occurred.
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