Brick (2005)

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Geeky outsider Brendan Frye is devastated when his ex-girlfriend Emily is found dead in a tunnel, having apparently landed herself in a spot of trouble with the local drug lord, The Pin. Guided by insider information from The Brain, Brendan retraces Emily's last steps, leading him to a rogue's gallery of classmates, including seductive rich girl Laura, vampish old flame Kara, hard-hitting thug Tugger, pot-head Dode and football jock Brad. As the truth slowly emerges, Brendan descends further into the criminal underworld, becoming embroiled in a bloody turf war between rival factions.