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?
- 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.
- Backstabbing the Alpha Bitch: Fern, as Vylette, once when she realizes that she has the power to overshadow Courtney, takes advantage of the attention given to her. That's when Courtney knocks her down a peg.
- Because You Were Nice to Me: Fern's liking of Liz was because she was nice to her. Even helping her gather her homework together when Liz's posse knocked it down.
- Chekhov's Gun: The Polaroid camera and Liz's birthday card.
- Deadly Prank: The premise of the film. Courtney and the others were going to surprise Liz for her 17th birthday, while kidnapping her, since the prank has gotten popular with others high schoolers... until the "joke" was on them. Generally, the prank wouldn't have been lethal but Courtney just had to use that jawbreaker without running it by Marcie and Julie first.
- Death by Sex: Courtney tries to set up Liz's death as such. Either to pin her up as being abused or her not being "so innocent and pure as she was thought to be". The catch? It fooled the police. At first, anyway.
- Did Not Think This Through: Courtney never stopped to consider the danger of stuffing a jawbreaker inside Liz's mouth before taping it shut until it was too late. Julie immediately calls out Courtney's stupidity after they learn what's making the lump in Liz's throat.Courtney: I just didnt want her to scream I thought a jawbreaker would be funny.
Julie: You gagged her with a jawbreaker?!
- Does This Remind You of Anything?: The popsicle scene.
- Dumb Blonde: Marcie fits this to a T, being very much on The Ditz end of the scale... until the High-School Dance.
- Engineered Public Confession: Before the climax, Julie discovers that an old record-message Birthday Card recorded Courtney's confession to the murder. With the help of Julie's boyfriend, who was on the Theater club, they set the message to play during Courtney's Prom Queen speech.
- Erotic Eating: Courtney uses it as part of sex play with her boyfriend, using a popsicle. Just to make him mime on what he wants her to do to him.
- 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.
- Even Evil Has Standards: Marcie isn't going to be dragged into Courtney's nightmare at the end.
- Even the Girls Want Her: Fern Mayo dropped off Liz's homework because she had a crush on her.
- 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.
- Goth: Julie befriends the Goths at school after she falls out with the clique.
- High-School Dance: The final location of the movie, and the site of...
- Humiliation Conga: Courtney didn't expect how awful her high school prom was going to be... especially when it is revealed that there was proof where she admitted to have killed Liz. "Eat shit," indeed.
- 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 Lizs 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.
- Incompatible Orientation: Fern Mayo (who's a closet gay or bisexual student) had a secret crush on Liz (who's straight).
- 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.
- Karma Houdini: Marcie doesn't really receive any comeuppance for her hand in things, as everything else is aimed at Courtney. Then again, she did decide, Screw This, I'm Outta Here!
- The Makeover: Fern's transformation into Vylette, in a rather... surreal sequence.
- Make Way for the Princess: The entire high school makes way for the breathtaking entrance of the Girl Posse.
- Meaningful Name: Fern. Lampshaded when she is renamed Vylette for this very reason.
- Missing Mom: Marcie's mother is out of the picture and she is quick to remind her dad that he's a single parent.
- Monochrome Casting: With the exceptions of Charlotte Ayanna, Pam Grier, and Tatiana Ali, the cast is predominantly white.
- My Nayme Is: According to the cast list, Fern's alter ego is named "Vylette" rather than "Violet"
- Narrator All Along: Fern, although it's not a huge surprise when you pay the slightest bit of attention in the first scene.
- Nice Mean And Inbetween: Julie (nice), Courtney (mean) and Marcie (in-between).
- Oh, Crap!: Courtney when her Engineered Public Confession is played on the public address system.
- Two-Teacher School: There's only four teachers shown at Reagan High School.
- Popular Is Dumb: Marcie is a little too willing to go along with whatever Courtney says.
- Punny Name: Detective Vera Cruz's name sounds like the Mexican port city "Veracruz"
- One Name Only: Fern's new identity as Vylette doesn't include a last name. Other characters lampshade this, comparing her to Madonna.
- Only Child Syndrome: None of the lead characters are shown to have any siblings.
- Outliving One's Offspring: Liz Purr dies before her parents.
- Pink Is Feminine: Fern, after her makeover into "Vylette" dresses in varying shades of pink.
- Screw This, I'm Outta Here!: Marcie abandons Courtney in the end, instead of being dragged to her Humiliation Conga.
- 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: Courtney is shamed by the students towards the end of the film after her involvement in killing Liz is revealed.
- 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.
- Smoking Is Glamorous: Fern starts to smoke after "becoming" Vylette.
- Shrinking Violet: Fern is your standard shy and quiet girl from High School that is not as beautiful as the Girl Posse and would be unnoticed by the crowd and the rest of her classmates. As a way to silence her about Liz's death, Courtney convinces her to "transform" into a different person. And this makes her more confident... and it works pretty well, even with a name such as Vylette.
- Stalker with a Crush: Fern Mayo was this to Liz Purr. She even calls her "The Cat's Meow"
- The Sociopath: Does Courtney mourn Liz's death? Just a little. Does she care about incriminating an unknown loser whom she had sex with, just to convince the police that neither she nor her "friends" were related to the case? Nope!
- Also, when the girls discover that Liz is dead, she is surprisingly a lot calmer than Julie and Marcie, who are both on the verge of panicking. This could easily be chalked up to her just being in shock, but still.
- Token Good Teammate: Liz among her friends, although Julie makes a HeelFace Turn throughout the movie.
- True Blue Femininity: Julie primarily dresses in blue.
- Trunk Shot: When the girls want to surprise Liz in one of the first scenes of the movie.
- Tuckerization: Ferns alter ego Vylette was named after a good friend of director Darren Stein.
- Vanity Plate: When Fern starts to embrace her new identity as Vylette she gets a red convertible with a vanity plate that reads BITCH
- Villain Protagonist: Courtney is about as conniving as they get but she also gets a good amount of screen time.