Jawbreaker (1999)

Jawbreaker is a 1999 American black comedy crime film written and directed by Darren Stein. Starring Rose McGowan, Rebecca Gayheart, Julie Benz, Judy Greer, Chad Christ, Ethan Erickson, Carol Kane, and Pam Grier, the film follows the "Flawless Four", the most popular girls at Reagan High School, who cover up the murder of fellow member Elizabeth "Liz" Purr after a kidnapping prank on her seventeenth birthday goes awry. When Fern Mayo (Greer) encounters the trio staging a crime scene with her body, Courtney Shayne (McGowan) and Marcie "Foxy" Fox (Benz) blackmail her into joining them, causing Julie Freeman (Gayheart) to question her place within the clique.

Stein initially conceived Jawbreaker as a horror film, but the screenplay instead developed as a teen film with elements of dark comedy, drawing inspiration from Carrie (1976) and Heathers (1988), as well as the films of John Hughes. Stein explained his concept for the film as, "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." Principal photography began in Los Angeles on January 18, 1998, and concluded on March 10.

Jawbreaker premiered at the Sundance Film Festival on January 30, 1999, and was theatrically released in the United States on February 19, 1999. The film received negative reviews from critics and was a box office failure, grossing $3.1 million against its $3.5 million production budget. Despite this, McGowan was nominated for the MTV Movie Award for Best Villain at the 1999 MTV Movie Awards. Initially panned as derivative of other teen films, the film became a cult classic in the years since its release, with McGowan's performance and the costumes in particular earning reappraisal.