Igby Goes Down

The film employs the ancient but ever-popular technique of showing the ending as its opening scene and then going back to pick up the narrative. We are introduced to Igby (Culkin), a bright troublemaker from a wealthy family who makes getting expelled from various educational institutions both an art and a hobby.  Eventually, his self-absorbed mother Mimi (Sarandon), sends him to military school, but he gets out of that too, taking a 'job' with his godfather and family friend D. H. Banes (Jeff Goldblum) that allows him to spend the summer wondering unsupervised around Manhattan.

He meets a girl named Sookie (Danes), a rare intellectual equal coming from a similarly odd family.  They like each other, but she also fancies Igby's ultra-Republican older brother Oliver (Phillippe), who isn't nearly as interesting, but is closer to her age.

Igby Goes Down has a genuinely distinctive brand of ultra-dark humour that doesn't call attention to itself by being conventionally deadpan or shocking.  Instead, Steers sets a sarcastically morbid tone that persists  through the entire movie, very much echoing the title character's unique personality.  We laugh not because what's on the screen is inherently funny or portrayed in a humorous way, but because it is filtered through Igby's deeply sardonic mind.

Most remarkably, the movie never resorts to sentimentality or easy conflict resolution.  It defies expectations through to the very end, delivering what would otherwise be show stopping plot revelations with deliberate offhandedness and avoiding the dramatic payoffs that seem to us inevitable.