As a kid, no one wants to end up like their parents, but Igby (Kieran Culkin) is more adamant about this than most.
His father (Bill Pullman) was a successful businessman until midlife, when the pressure came crashing down on him in waves he could no longer bear. Igby feels that by rebelling against that life now he can skip the long and tortured path his father took and therefore skip the breakdown as well.
The film explores the pressures of different strata of society and although it takes various forms it always has the same intensity. Each character suffocates unless they can find some occasional release—whether it’s pill popping or affairs—that can make their lives at least temporarily bearable.
In a world of wealth and privilege all Igby sees is the lack of real sentiment inherent to such a way of life. He laughs bitterly as his godfather (Jeff Goldblum) parades his mistress at a party his wife is hosting while all her friends watch and say nothing to help her. The façade of pleasantries covering the reality of back-stabbing and self-interest is so obvious and nauseating to Igby that he rejects it all.
There is a large cast of characters that inhabit Igby’s world, but he finds it impossible to connect with any of them—he’s beaten up by a few of them and betrayed by the rest. His past of prep school failures gives him an educated wit and sarcasm and the breakdown of his family gives him a tragic anger that Kieran Culkin does a superb job of bringing across on screen.