32. Deadgirl (2008)
Director: Marcel Sarmiento and Gadi Harel
Deadgirl could have justifiably been called Not Another Teen Movie, because, well, it's anything but your typical coming-of-age high school story. The two main characters (played by Shiloh Fernandez and Noah Segan) are, yes, teenagers, and many of the film's scenes take place in a high school. But name another teen flick that spends most of its duration inside a decrepit old institution and shows its protagonists raping and exploiting a naked, undead female.
And how's this for a statement about premarital relations: One character's intestines burst out of his ass after the titular "dead girl" bites his penis off during oral sex. Rumor has it that was actually in the first draft of Superbad's script. Go figure.