6. "Igby Goes Down" (2002)

As quick-witted yet miserably frustrated Igby, a magnificent Kieran Culkin gives life to writer-director Burr Steers' intense look at privileged Upper East Siders. Overflowing with angst distilled from a schizophrenic father, a pharmaceutically-suppressed tyrant mother (played with impeccable coldness by Susan Sarandon) and a brother in the Young Turks, Igby runs away from parochial school and his narcissistic family to live in a "Boho version of the Island of the Lost Toys." While Culkin's deadpan sarcasm and unbridled insults more than fulfill the requirements of this list, they also add a sense of levity.

Angst-ometer rating: 8

Sample quote: "I'm drowning in a--holes."

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