My favorite genre. Until a few years ago I would've told you The Thin Man
What makes this film work so well is the authenticity of the film noir lingo, and the way Joseph Gordon-Levitt embodies the conflicted "heroes" of the genre's golden age in the 1930s and 40s. He's a guy who looks upon the upper crust of his school with scorn, but we're not really sure why he hates them so. Is it jealousy? Does he secretly desire to be one of them? Whatever his reasons, it drives his every action. Every decision he makes is somehow linked to his feelings towards these people, and they in turn visit upon him the same level of hatred. Beautiful femme fatales(like Nora Zehetner!)tempt him at every turn, always hiding their true motivations. New mysteries and complications around always right around the corner, often leading to our hero getting his butt kicked and having to pull himself up by his boot straps to keep going.