The end scene to "Fight Club" with "Where is my Mind" by the Pixies. Always thought of it as a rather creepy song and it only enhances the scene.
The music used in the backround of this scene from Le Fabuleux Destin d'Amélie Poulain only enhances the madness of it.
And of course all the old John Hughes films (Sixteen Candles, Pretty in Pink, Ferris Bueller's Day Off).
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