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Janey Briggs

Portrayed By: Chyler Leigh
The pretty ugly girl

  • Beautiful All Along: Parodied in her "transformation" scene. She looks beautiful without glasses and ponytail!
  • Butt-Monkey: On top of being poor, she takes a lot of physical punishment. She falls through a flight of stairs and gets tased by the police.
  • Caught with Your Pants Down: Parodied: Janey tries to have some "alone time" with a dildo on her eighteenth birthday, when her parents, grandparents, siblings, family pets, pastor, and the girl scout troop she mentors enter in quick succession.
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  • Covered in Gunge: This happens to Janey and everyone else in the opening scene, as the result of a catastrophic encounter between her vibrator and her birthday cake. It happens again, turned Up to Eleven, with the scene with the Dainty Girl on the toilet.
  • A Date with Rosie Palms: Janey's opening scene, in a gender-swapped parody of American Pie. Becomes a Chekhov's Gag at the finale.
  • Expy: Laney from She's All That.
  • Floorboard Failure: Janey's slow-motion entrance down the stairs of her home is somewhat undermined by this, compounded by the stair carpet, landing table, stair rods and sundry stairs and other bits of the house falling on top of her.
  • Glasses and Ponytail Coverup: Parodied, obviously, with Janey Briggs being the most unattractive girl ever for having glasses and a ponytail, with everyone reacting appalled. When her date's sister pseudo-erotically removes them, everyone reacts as if she has become the most attractive girl in the world, and asking who she is at prom.
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  • The Glasses Gotta Go: This plus taking her hair out of a ponytail is all Janey needs to be revealed as Beautiful All Along.
  • Hollywood Homely: Parodied In-Universe. Jake, the popular jock, has to make Janey beautiful because... you know, she's hideous! Just look at the glasses! And her ponytail! And the paint-covered overalls! And this in comparison to an albino hippy, a hunchback, and conjoined twins.
  • Informed Ability: Parodied. Janey's "artistic talent" is essentially just drawing kindergarten-level stick figures. It's a bit strange how she draws them with wild, violent Jackson Pollock-like techniques, though.
  • Informed Flaw: Janey's case of Hollywood Homely.
  • Intimate Artistry: Parodied. Janey's character is a parody of the rebel/angry artist character type who expresses her feelings through her painting. However, despite other characters talking about how good her work is, she is only ever shown producing childlike stick-figure paintings. In one scene, where she is actively shown painting in an energetic, angry style (Throwing paint at the canvas and overcome with emotion), the final result is again just a kindergarten-level drawing.
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  • Oblivious to Love: Ricky has no problem with Cannot Spit It Out - he writes a 10 Things I Hate About You-esque poem (entitled "Ten Things I Love About Janey Briggs") flat-out confessing his love for Janey and reads it aloud in class, while other students are heard groaning, "Not again." She still doesn't pick up on it.
  • Tomboyish Ponytail: Spoofed over how it was supposed to make her unattractive.

Jake Wyler

Portrayed by: Chris Evans
The popular jock
  • Accidental Murder: Jake does not have the best luck when it comes to football.
  • Big Man on Campus
  • Even the Guys Want Him: During the scene where girls are throwing their underwear at him, one guy gives him his jockstrap.
  • Expy: Zack from She's All That.
  • Follow in My Footsteps: To the point that his father just asks him to give Princeton 4 years, before bringing in the perfect rebound girl for Jake - his mother.
  • Lovable Jock: While Jake is certainly the Big Man on Campus, he's really not a bad guy. Spoofed however when he tries to be the "sensitive guy" by protecting his Love Interest's little brother from being bullied, only to receive an accidental punch to the face in return. Jake kicks the shit out of him in response.
  • Mr. Fanservice: The banana split scene.
  • Only Sane Man: Considering that Catherine wants to sleep with him, and his dad wanted his wife to sleep with him to really make sure Jake would Follow in My Footsteps, Jake is the only person who sees this as beyond messed up.
  • The Quarterback: Jake being a fulfilling parody of this character should really be expected.
  • Race for Your Love
  • Would Hit a Girl: Slugs Priscilla for embarrassing Janey at Preston's party, amidst a slew of And This Is for... blows.

Austin

Portrayed By: Eric Christian Olsen
The cocky blonde guy
  • Big Bad: He sets up all the drama between Janey and Jake
  • Jerk Jock: As unpleasant as it gets

Catherine Wyler

Portrayed by: Mia Kirshner
The cruelest girl
  • Anything That Moves: Has sex with total strangers before getting with Ox because he can't believe no one's ever taken a dump on her chest.
    • Earlier, she leaves Jake and Janey alone by announcing that she plans on fucking a complete stranger - cue a chorus of guys saying "I'm a complete stranger!"
  • Brother–Sister Incest: Wants to have sex with her own brother, mostly because she's had pretty much everyone else already.
  • Depraved Bisexual: Ranging from May–December Romance to Brother–Sister Incest.
  • Expy: Of Kathryn from Cruel Intentions.
  • Girl-on-Girl Is Hot: Subverted in the scene where Catherine frenches an old woman, which is made repulsive. Also subverted in Janey's "transformation", when Catherine looks about to kiss her, then about to go down on her.
  • Really Gets Around: Despite wanting to have sex with her brother, Catherine had sex with nearly every guy (and girl) she takes an interest to. Even twice.
    • Which is probably a big factor as to why she wants to have sex with Jake - because what else is left?
  • Single Woman Seeks Good Man: After losing her chance at Jake, she confides in Ox that she wishes she could meet a nice, sensitive guy who's interested in more than just sex. She wants a guy who'll take her out to dinner, and would then take a dump on her chest for once.

Ricky Lipman

Portrayed by: Eric Jungmann
The obsessed best friend
  • Butt-Monkey: Poor, sweet Ricky. He tells Janey that he's in love with her to her face, only for her to completely ignore him. Ends up broken and battered trying to beat the Big Man on Campus to the Airport, as he gets hit by a couple dozen cars. Ends up starting the Slow Clap... which gets him beaten up again.
  • The Chew Toy: The final Race for Your Love against Jake has Jake encounter smooth sailing, while Ricky encounters a locked door at the start, almost get run over by a half-dozen cars (whose drivers all shout variations on "She doesn't love you!"), does get run over by a passing bicycle, narrowly avoids different bikes at Janey's house before getting embedded in a bus' front grill, and upon arriving at the airport, tries to give a romantic speech... only to be curtly informed that Jake had used the same line to get through, and no one was falling for it again.
  • Dogged Nice Guy: As dogged as it gets.
  • Expy: Of Ducky from Pretty in Pink.
  • Just Friends: Janey doesn't even bother to tell Ricky she just likes him as a friend, as she's Oblivious to Love.
  • No Sympathy: Aside from the above, a random woman at the airport chastises him for bleeding on her suitcase.
  • Unlucky Childhood Friend

Mitch Briggs

Portrayed by: Cody McMains
The desperate virgin

Priscilla

Portrayed by: Jaime Pressly
The nasty cheerleader.

Supporting Teens

Malik

Portrayed by: Deon Richmond
The token black guy
  • Catchphrase: Lampshades this: "I'm just supposed to smile, and stay out of the conversation, and say things like 'Damn!', 'Shit!' and 'That is whack!'" Later, there is this brilliant exchange:
    Token Black Guy: *clears throat*
    Other Black Guy: what?
    TBG: I'm supposed to be the only black guy at this party.
    OBG: Damn!
    TBG: Yeah...
    OBG: Shit!
    TBG: I know—
    Both: It's whack!
    OBG: *leaves*
  • Sophisticated as Hell: Delivered a very deep and insightful speech to Jake near the end. When Jake pauses to thank him, then dashes out abruptly before he can reply, he says only one word: Motherfucker.
  • Token Minority: Save for one brief moment where another black guy appears.

Reggie Ray

Portrayed by: Ron Lester
The stupid fat guy

Ox

Portrayed by: Sam Huntington
The sensitive virgin
  • Expy: Oz from American Pie
  • My Girl Is a Slut: His response to Catherine's impassioned plea for a guy to take a dump on her chest for once is to be mortified that none had.

Bruce

Portrayed by: Samm Levine
The Asian wannabe

Amanda Becker

Portrayed by: Lacey Chabert
The perfect girl
  • Big Entrance: Lampshaded at the party, as everyone freezes as she walks in - and the tour guide from the start shushes another guy and quietly explains that they can't talk until she starts moving again.
    Random Woman: She took forever this time!
  • Expy: Amanda from Can't Hardly Wait.
  • Satellite Love Interest: Exists purely for Mitch to fawn over.

Areola

Portrayed by: Cerina Vincent
The foreign exchange student

Kara & Sara Fratelli

Portrayed by: Samaire Armstrong and Nectar Rose
The prom queens

Les

Portrayed by: Riley Smith
The beautiful weirdo

The Tour Guide

Portrayed by: Josh Radnor
The exposition guy

Preston Wasserstein

Portrayed by: Rob Benedict
The house party guy

Adults

Mr. Briggs

Portrayed by: Randy Quaid
Janey and Mitch's dad.

Coach

Portrayed by: Ed Lauter
The goddammed coach, goddammit!

Sadie Agatha Johnson

Portrayed by: Beverly Polcyn
The undercover reporter

The Wise Janitor

Portrayed by: Mr. T
The wise janitor
  • Ambiguously Gay: He'd been watching Jake for a long time, including in the locker room showers whipping other guys with a towel.
  • Leitmotif: The theme to The A-Team.
  • Magical Negro: Played by Mr. T. Naturally.
  • Meaningful Background Event: The wise janitor can be seen in the background during some scenes in the football field before his appearance in the big football game.

Molly Ringwald

The woman herself. Currently working as a flight attendant to get by.
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