Zyzzyx Road (2006)

Why the tears, Kat? Maybe it's because this is the flick that made headlines for being the lowest-grossing movie of all time — pulling in a paltry $30 at the box office. For the countless billions of you who did not make it to the theater that weekend: It's a thriller starring Heigl (who landed the role right after she'd been cast in an ABC pilot by the name of Grey's Anatomy) as a randy teenager caught in a lust triangle with an accountant and her hot-tempered boyfriend (played by Tom Sizemore).

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