Portrayed By: Chyler LeighThe 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.
- 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.
- 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.
- 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.
Portrayed by: Chris EvansThe 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.
Portrayed By: Eric Christian OlsenThe cocky blonde guy
Portrayed by: Mia KirshnerThe 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!"
- BrotherSister Incest: Wants to have sex with her own brother, mostly because she's had pretty much everyone else already.
- Depraved Bisexual: Ranging from MayDecember Romance to BrotherSister 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.
Portrayed by: Eric JungmannThe 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
Portrayed by: Cody McMainsThe desperate virgin
Portrayed by: Jaime PresslyThe nasty cheerleader.
- Alpha Bitch
- Blatant Lies: Priscilla denies it when she is accused of stealing the cheers of the all-black North Compton Wildcats squad, why do I have to mention they are an all-black squad? Because the cheer lyrics not only mention they are the North Compton Wildcats but that they "Definitely ain't white." Which is unusual for an all Caucasian cheer squad to be singing.
- The Cheerleader
- Contrived Clumsiness: Parodied. Janey is already wet from jumping into the pool when Priscilla, sarcastically feigning clumsiness, spills a bottle of WATER on her. Janey reacts with humiliated tears.Random Party-Goer: That's gonna stain!
- Smurfing: The Alpha Bitch wants you to remember the following.Priscilla: Let's get one thing straight - this is not a cheer-ocracy. I am the cheer-tator, I make the cheer-cisions around here, and I will deal with the cheer-onsequences.
Portrayed by: Deon RichmondThe 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 knowBoth: 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.
Portrayed by: Ron LesterThe stupid fat guy
- Expy: From Varsity Blues, also doubling as an Actor Allusion, right down to a "Reggie Ray Concussion Countdown" on the scoreboard at the football game.
Portrayed by: Sam HuntingtonThe 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.
Portrayed by: Samm LevineThe Asian wannabe
- Expy: Kenny from Can't Hardly Wait. It's also probable he's a race-flipped parody of Long Duk Dong from Sixteen Candles - i.e. an Asian and Nerdy Immigrant who is trying way too hard to be American.
- N-Word Privileges: Calls some Asian guys "chinks". One of them kicks him in the chin for that.
- Pretty Fly for a White Guy: Only instead of trying to be black, he's trying to be Asian.
Portrayed by: Lacey ChabertThe 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.
Portrayed by: Cerina VincentThe foreign exchange student
- Disney Creatures of the Farce: During the "Prom Tonight" sequence, a nude Areola sings out her window while Disney-style cartoon birds appear and sing with her.
- Europeans Are Kinky: Parodied with Areola, the foreign exchange student who is constantly nude.
- Expy: Nadia from American Pie
- Foreign Exchange Student
- Foreign Fanservice: Always naked. Lampshaded, of course."I am here to be object of lust for poor nerds who can't get American pussy!"
- Fun with Subtitles: Whenever Areola is naked and speaking, the subtitles avoid covering her 'assets'.
- Funny Foreigner: Her accent changes every line and she dodges the question of what country she's from in a deleted scene.
- Just a Stupid Accent: Areola's accent changes between scenes, and in one scene she even randomly switches from an Indian to a British accent without missing a beat.
- Meaningful Name: "Areola" is the name for the area of skin surrounding the nipples, and she is always seen naked.
- Naked People Are Funny: Made funnier in that Cerina Vincent used to play a Ms. Fanservice on Power Rangers Lost Galaxy just two years prior.
- Non-Specifically Foreign: "European" is about as close as you're gonna get (and even then, she does an Indian accent and Asian Speekee Engrish later in the film). While saying "grazie" when Janey complimented her backpack might lead you to Italian, her accent changes with every scene.
- Unusually Uninteresting Sight: Outside of her introduction, and the other naked girl at the party who complains that she copied her outfit, no one makes any comments about her walking around in the buff.
- What the Hell Is That Accent?: Played for laughs. Areola's accent changes throughout the movie.
Kara & Sara Fratelli
Portrayed by: Samaire Armstrong and Nectar RoseThe prom queens
Portrayed by: Riley SmithThe beautiful weirdo
The Tour Guide
Portrayed by: Josh RadnorThe exposition guy
Portrayed by: Rob BenedictThe house party guy
- Expy: Of Ferris Bueller.
- A Party, Also Known as an Orgy: Blatantly tells his parents that he's going to bring hookers into their house.
Portrayed by: Randy QuaidJaney and Mitch's dad.
- The Alcoholic: His defining character trait.
- Hypocritical Heartwarming: He expresses surprising tenderness towards his kids, especially Janey, but his alcoholism always makes his advice... a bit skewed.
- Shell-Shocked Veteran: Towards the end of the film he starts having flashbacks of Vietnam.
Portrayed by: Ed LauterThe goddammed coach, goddammit!
Sadie Agatha Johnson
Portrayed by: Beverly PolcynThe undercover reporter
The Wise Janitor
Portrayed by: Mr. TThe 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.