Of his concept for the film, Stein has stated "The jawbreaker just came to represent the duality of the poppy sweetness of the girls, of high school and of youth, versus the whole idea that this thing could break your jaw". The film was released on February 19, 1999 and was a critical and financial failure, although it has come to gain a cult following. Similarities have been drawn between Jawbreaker and the 2004 film Mean Girls.
On the morning of her 17th birthday, high-school senior Liz Purr (Charlotte Ayana), the most popular girl in Reagan High, is kidnapped in her bed by three masked assailants, one of whom stuffs a jawbreaker into her mouth as a gag before she is placed in the trunk of a car. The kidnappers turn out to be Liz's "friends"—Courtney (Rose McGowan), Marcie (Julie Benz), and Julie (Rebecca Gayheart) -- playing a cruel prank on her for her birthday. When the girls drive up to a diner to treat Liz to breakfast, they pop the trunk and discover she is dead, having choked to death on the jawbreaker jammed in her throat by Courtney just before slamming the trunk of the car.
Julie wants to go to the police, but Courtney forbids her. Courtney calls the school pretending to be Liz's mother and tells them Liz is ill and cannot attend school, then the three go to school as though nothing had happened. Fern Mayo (Judy Greer), school outcast and fervent admirer of Liz Purr (whom she calls "The Cat's Meow"), is sent by the school principal, Miss Sherwood (Carol Kane), to deliver Liz's homework at the end of the day, she stumbles upon the three girls at Liz's house trying to arrange her body in bed. Courtney tries to fabricate a story that Liz died at the hands of a rapist.
Fern attempts to flee the house, but the girls catch her and Courtney buys her silence by accepting her into the clique, telling her to take Liz's place, despite Julie's protests. Courtney and Marcie give Fern a makeover, transforming her from plain and awkward to elegant and beautiful. The transformation is so complete, Courtney introduces Fern as the beautiful exchange student "Vylette".
Julie, overwhelmed by guilt at her part in Liz's death, breaks away from the clique, only to be reviled by Courtney and Marcie. As her popularity dissolves, she becomes a new target for abuse and contempt throughout the school. Her only real friend during this time is her boyfriend, a drama student named Zack (Chad Christ).
As Vylette's popularity soars, Julie watches in silence as Courtney spins an endless web of lies to cover up the murder and maintain her popularity. Julie threatens to go to the police and tell the truth, but Courtney retorts that she, Marcie, and now Vylette will claim Julie killed Liz if she attempts to expose them. To her disgust, Julie learns that, after they had returned Liz's corpse to her house, Courtney went out that same night and seduced a stranger (Marilyn Manson) at a sleazy bar and had sex with him in Liz's bed in order to frame him for the murder.
Vylette becomes intoxicated with her new-found popularity, which has eclipsed Courtney's own. Courtney orders Vylette to learn her place, but Vylette vows that if Courtney does not watch her step, then she will reveal the truth behind Liz's death. In response, Courtney and Marcie post enlarged yearbook photos of Fern Mayo all over the school with the message "Who is Vylette" written on them, revealing Vylette's true identity and leaving her humiliated by the entire school. Julie takes pity on Fern and forgives her for being corrupted by Courtney.
Feeling no remorse for the lives she has destroyed, the heartless Courtney attends the senior prom with jock Dane Sanders (Ethan Erickson). Meanwhile, Julie is at home going through a bag of Liz's belongings that were given to her. Upon finding a recordable greeting card she was fiddling with when Courtney was faking Liz's death scene, on which Courtney's admission to the killing (callously saying "I killed Liz. I killed the teen dream. Deal with it") was inadvertently recorded. Armed with this evidence, Julie, Fern and Zack hurry to the prom.
When Dane and Courtney are announced as Prom King and Queen, Zack sneaks backstage and broadcasts the card's message over the sound system. Disgusted, Dane quickly abandons Courtney while Marcie hides under a table. Horrified that her scheme has unraveled, Courtney races for the exit as the rest of the furious students pelt her with corsages and other projectiles and call her a murderer. Julie snaps a picture of Courtney to immortalize the occasion. As Courtney's photo ends up in the yearbook, the film closes with one of Fern Mayo's quotes to Detective Vera Cruz: "This is high school, Detective Cruz. What is a friend, anyway?"Rose McGowan as Courtney Shayne
Rebecca Gayheart as Julie Freeman
Julie Benz as Marcie "Foxy" Fox
Judy Greer as Fern "Vylette" Mayo
Chad Christ as Zack Tartak
Charlotte Ayanna as Elizabeth "Liz" Purr
Ethan Erickson as Dane Sanders
Pam Grier as Detective Vera Cruz
Carol Kane as Ms. Sherwood
Marilyn Manson as The Stranger
Tatyana Ali as Brenda
William Katt as Mr. Purr
P. J. Soles as Mrs. Purr
Jeff Conaway as Mr. Fox
Director Darren Stein brought his script to executives at Columbia Tri-Star, who agreed to finance the film if he could cast either Natalie Portman, Kate Winslet or Rose McGowan. The role of Julie originally went to Rachael Leigh Cook, who was eventually replaced with Rebecca Gayheart because the producers felt she didn't have the right chemistry with the two other actresses. Marilyn Manson, who was then dating Rose McGowan, agreed to appear in a non-speaking cameo role.
On a small budget of $3.5 million, Jawbreaker was filmed at locations in and around the Los Angeles area. 'Reagan High School' was actually University High School in West Los Angeles, with the cafeteria scenes filmed at Notre Dame High School in Sherman Oaks. The diner that the girls drive up to at the beginning of the film is Johnie's Broiler in Downey, California, the filming site for many film and television productions.
The distinctive costumes were designed by Vikki Barrett, who drew on 1980s and 1950s-era fashion trends blended with fetishistic elements like lycra skirts, all in bright, candy-like colors to evoke the jawbreaker.
Before the film could be released, the MPAA objected to a graphic sex-scene between McGowan's and Marilyn Manson's characters, which had to be cut down to give the film an R rating instead of an NC-17. To accompany the release of the film, Imperial Teen's music video for the song Yoo Hoo featured McGowan as Courtney Shane harassing the band members with jawbreakers.
Critical response was overwhelmingly negative. It currently holds a 7% approval rating at Rotten Tomatoes based on 57 reviews (four positive, 53 negative), leading to its inclusion on several of the websites lists ranking the worst films, earning the distinction of being the single worst film of 1999, as well as ranking among the top-ten worst films of the 1990s.
Roger Ebert gave the film one and a half out of four, stating "The movie is a slick production of a lame script ... If anyone in the plot had the slightest intelligence, the story would implode". Francesca Dinglasan from Boxoffice magazine gave the film one and a half out of five, criticizing the film's humor and similarities to Heathers.
James Berardinelli gave the film a more favorable two and a half out of four, calling it "palatable, and occasionally even clever", but concluding, "while the film offers more than a Heathers rehash, it never fully develops its own identity.
McGowan was nominated for the MTV Movie Award for Best Villain, but lost to Matt Dillon and Stephen Dorff for their roles as Pat Healy and Deacon Frost in There's Something About Mary and Blade.
Despite the negative critical feedback, Jawbreaker found success through home video release and subsequent television airings; it has developed a cult following. Vice Magazine called the film a 'teen classic' when it published a retrospective in 2016 entitled "Perverting the Youth of America: The Oral History of Teen Classic Jawbreaker". Dazed Magazine published a similar feature, crediting the film with inspiring 2004's Mean Girls, and praising the dark tones and performances.
McGowan's Courtney Shayne has become something of a pop culture icon on social media, with TribecaFilm.com declaring of McGowan's performance that "...every single line-reading was a thing of Bette Davis-aspiring beauty, and with any justice, it's a performance that will only grow in esteem over time."
Jawbreaker's costumes have also been celebrated, drawing praise from the likes of Vogue and Rookie magazines. The scene where the actresses strut down the hallway in slow-motion to Imperial Teen's Yoo Hoo has become a signature feature of the film, drawing homage in film and television, most notably Mean Girls, and being parodied in films like Not Another Teen Movie (2001).The Cars, "Good Times Roll"
Connie Francis, "Lollipop Lips"
The Friggs, Heartbreaker (Pat Benatar song)
Veruca Salt, "Volcano Girls" Opening Scene
It was announced in February 2017 that the film will be reimagined as a television series for the E! Network. Darren Stein, the writer and director of the original film, will write and produce the series. The project is currently in its development stage.