The movie starts with the popular girls of Reagan High fake-kidnapping one of their group, Liz Purr (Charlotte Ayanna), as part of her seventeenth birthday, only to find when they arrive that she has choked to death on the jawbreaker candy that they used to gag her. Alpha Bitch Courtney Shayne (McGowan) then leads the others to create an elaborate cover story that would paint Liz's death as an accident resulting from a kinky sexual encounter and get them off scot-free.
One of the girls, Julie Freeman (Gayheart), struggles to come to terms with what they've done and is summarily shunned by Courtney and her lapdog, Marcie Fox (Benz). On top of this, she is replaced by the geeky Fern Mayo (Greer), who Courtney transforms into the glamourous Vylette in return for the girl's silence. But the attention lavished upon "Vylette" soon goes to Fern's head and she begins to encroach on Courtney's position as the Queen Bee, only to discover exactly why that was a bad idea as she is publicly humiliated. Meanwhile, when Julie is given a box of Liz's possessions, she stumbles upon something that will prove to be Courtney's downfall just as she prepares to accept the title of Prom Queen that Liz's death left her free to claim.
Tropes in this film include:
- The '90s: Jawbreaker encapsulates the trends that were popular during the decade, such as fashion, articles and objects, Talk Shows talking about how "the crowd influences on others", the use of Dawson Casting on behalf of the movie's cast, Marilyn Manson having a cameo in the movie...
- Accidental Murder: Liz's cause of death? Choking on a jawbreaker that her friends (specifically, Courtney) used to gag her while fake-kidnapping her. The duct tape didn't help.
- Adults Are Useless: So no principals or teachers have a problem with the girls parking directly in front of the school?
- All Gays Love Theatre: Courtney says that since Zack is in the drama club "we can't guarantee hetero status", although he is Julie's love interest. There is additionally a Camp Gay student in the scene where Vylette introduces herself to Zack.
- Asshole Victim: Subverted with Liz, who was a genuinely sweet, friendly girl. However, Courtney does her best to make her seem like this, making up a story for the police about Liz seducing older men and bringing them back home to have sex with.
- Bare Midriffs Are Feminine: All three members of the bitchy queen bee trio are shown with bare midriffs on the poster. More specifically, in the film itself:
- Courtney wears a cropped sweater during her Make Way for the Princess walk after Liz's death.
- When Fern transforms into Vylette and Courtney realizes that "Vylette" is becoming more popular than she is during a scene where she's almost attacked by a baying mob, Vylette/Fern is wearing a pink crop top that says "BITCH".
- Bound and Gagged: The other girls tie up Liz and gag her with the titular candy in a mock kidnapping prank. The "gagged" portion of this trope ultimately proves fatal for her when the jawbreaker lodges in her windpipe.
- The Cameo: Marilyn Manson cameos as a man in a bar whom Courtney frames for Liz's murder.
- Casting Gag: Liz's parents are played by William Katt and P.J. Soles, who played Tommy and Norma in Carrie (1976), one of the major inspirations behind this film.
- Chekhov's Gun: The Polaroid camera and Liz's birthday card.
- Class Princess: Liz was described by the narrator as the "Princess Di" of Reagan High, ruling with kindness, which really pissed off her Alpha Bitch friend, Courtney, and which made her early tragic death all the more awful.
- Crapsaccharine World: The movie's aesthetic is bold and colourful, with all characters in brightly vibrant clothes, and even somewhat colourful backdrops at school. And then the popular girls cover up their accidental murder of a friend, and much backstabbing ensues.
- Deadly Prank: The mock kidnapping, which turns fatal when Liz chokes to death on the jawbreaker candy stuffed in her mouth as a gag. Borders on Deadly Hazing, given the lengths the girls go to make the kidnapping seem real.
- Died on Their Birthday: Liz ends up dying on her 17th birthday when she chokes to death on the jawbreaker that her friends used to gag her in a kidnapping "prank" that goes awry.
- Does This Remind You of Anything?: The popsicle scene.
- Establishing Character Moment: The opening shot of the film is Courtney, Marcie, Julie, and Liz walking down the hallway, while Fern drops some papers in front of them. While the other three walk past without so much as a passing glance, Liz stops to help Fern pick up her things. This establishes her as the Nice Girl of Courtney's Girl Posse, making her death much sadder.
- Everyone Has Standards:
- Dane initially seems like a dumb Jerk Jock, fittingly as Courtney's prom date. But he is among the first to be disgusted with her when she's exposed. He even walks off the stage, showing her she's on her own.
- Vylette becomes a very quick example when Courtney and Marcie get sick of her and expose her past as Fern, putting her back at the bottom of the food chain.
- Gone Horribly Wrong: The girl's prank on Liz for her birthday goes horribly wrong as they smothered her cries with a jawbreaker and duct tape ultimately leading to her death.
- Hated by All: The moment Courtney's exposed as Liz's murderer, the entire student body immediately turn on her and start calling her all sorts of horrible things as they pelt her with corsages.
- High-School Dance: The final location of the movie, and the site of...
- I Did What I Had to Do: Said practically verbatim by Courtney, but kinda subverted due to the fact that what she "did" was get some poor loser charged with Liz's murder just to save her own ass.Julie: They found some poor guy and they charge him with murder? What have you done, Courtney?! What have you done?
Courtney: It's just what I had to do, dear.
Julie: What? Destroy another life, Courtney?
Courtney: Life's a bitch, then you die.
Julie: No honey, you're the bitch!
- Idiot Ball: Courtney. When Fern/Vylette pissed her off, why didn't Courtney just find out a way to blame her? The fact that Fern had conveniently disappeared beforehand would have made it easy for Courtney to pawn the murder off on her!
- Innocent Blue Eyes: Liz, Julie, and Fern are all blue-eyed and of varying degrees of innocence. Liz is the Token Good Teammate who treated the school populace with kindness, Julie pulls a Heel–Face Turn after seeing Courtney show no remorse for killing her childhood friend, and Fern starts off innocent before her newfound popularity goes to her head.
- In with the In Crowd: Fern and Julie both apply. Marcie's talk with her father implies that this is also what happened to her.
- Loved by All: Liz was adored by just about everyone because she was a kind person who was nice to everybody. Courtney being exposed as her murderer leads to all the other students immediately hating her with a passion for killing someone as good as Liz was.
- Make Way for the Princess: The entire high school makes way for the breathtaking entrance of the Girl Posse.
- Mass "Oh, Crap!": This is pretty much everyone's reaction at Prom when they first hear the Engineered Public Confession. But that shock lasts for all of five seconds once they realize that it's Courtney's voice.
- Menacing Mask: Julie, Courtney, and Marcie wear the make-up wearing variety of clear plastic masks along with black hoodies to abduct Elizabeth from her room as a birthday prank. A prank that goes horrifically wrong when Elizabeth ends up choking on the jawbreaker used to gag her.
- Meaningful Name: Fern. Lampshaded when she is renamed Vylette for this very reason.
- Monochrome Casting: With the exceptions of Charlotte Ayanna, Pam Grier, and Tatiana Ali, the cast is predominantly white.
- Naughty by Night: The lie Courtney wants to use to explain how Liz died was that she was killed by one of her many lovers, who just got a little too rough one night. Since School Idol Liz's reputation was spotless, Julie says no one is going to believe it. Courtney argues that is precisely the reason why.Courtney: They'll believe it, because it's their worst nightmare. Elizabeth Purr, the very picture of teenage perfection, obliterated by perversion?
- Nice Mean And In Between: Julie (nice), Courtney (mean), and Marcie (in-between).
- Oh, Crap!: Courtney when her Engineered Public Confession is played on the public address system.
- One-Word Title: A Portmantitle for the jawbreaker candy, cause of the Inciting Incident that is Liz Purr's death.
- Outliving One's Offspring: Liz Purr dies before her parents.
- Pink Is Feminine: In her brief moments, Liz Purr is seen in this color with classically feminine styles to underscore how beloved she was by the school for her beauty and kindness.
- Popular Is Evil: Three out of four members of the Girl Posse are cruel, vapid and heartless. The one good member is killed accidentally at the beginning of the movie. When they makeover Fern to buy her silence and becomes popular at school, the newfound status goes to her head, and she becomes just as bitchy as Courtney.
- Posthumous Character: Liz dies in the opening five minutes, but continues to influence the story by how she's remembered.
- Punny Name: Detective Vera Cruz's name sounds like the Mexican port city "Veracruz".
- Sex Is Evil: Liz was a virgin, and was described and seen as a pure and kind person. Courtney, while being the evil mind behind the entire joke, being manipulative as possible... wasn't.
- Shamed by a Mob: As soon as Courtney is exposed as Liz's killer at the prom, she's assaulted by a barrage of corsages as everyone screams vulgarities at her and call her a murderer.
- Small Role, Big Impact: Liz Purr has no lines and is only seen alive for the first few seconds of the movie, but it's her Accidental Murder and the efforts to cover it up that compose the plot of the movie.
- Token Good Teammate: Liz among her friends, although Julie makes a Heel–Face Turn throughout the movie.
- Trunk Shot: When the girls want to surprise Liz in one of the first scenes of the movie.
- Tuckerization: Fern's alter ego "Vylette" was named after a good friend of director Darren Stein.
- Two-Teacher School: There are only four teachers shown at Reagan High School.