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With special guest Jeff from Notable Nostalgia! Jawbreaker is a 1999 American black comedy film written and directed by Darren Stein. The film stars Rose McGowan, Rebecca Gayheart, and Julie Benz as girls in an exclusive clique in their high school. Charlotte Ayanna has a non-speaking cameo role as the murdered fourth member of the group. The film was inspired by the 1988 film Heathers, and is often compared to it, particularly the plot involving a popular female clique, the use of bright pastels, and the ostensibly accidental killing of one of its members.

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".[2] 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, Heathers and the 2004 film Mean Girls.