Opens Fri Sept 20 at various theaters.

The most memorable literary criticism I ever heard leveled at The Catcher in the Rye came from a kid I used to work with at a minimum-wage job. He admired the structure and style of the novel, and conceded that Salinger was great at combining humor and pathos. There was one thing, however, that prevented him from fully embracing the book: He hated Holden Caulfield.

"He's a whiny little bitch," he said. (I remember because I wrote it down.) "How am I supposed to believe someone who has enough money to check into a New York hotel is really hitting bottom?"

Though I couldn't share my coworker's unappreciation of old Holden, his conviction--which I later discovered was shared by many--made me realize why there could never be a movie version of The Catcher in the Rye. A film would have to show what Holden really looks like--a rich, young, preppy elitist--which would make most audiences squirm with class contempt.

Whether or not Holden really suffers may be open to debate (for the record, though, he does). But in an age of characters you have to identify with, there's little doubt that the tribulations of a ruling-class hero are about as compelling as a cold sore to most audiences.

This dilemma is somewhere near the heart of Igby Goes Down, an excellent film about a punky prep-school dropout (Kieran Culkin) making his weary way down the Via Dolorosa--armed with a purloined credit card, beset by some serious Oedipal issues, and abetted by a nouveau-riche land-baron uncle (Jeff Goldblum), his junkie trophy girlfriend (Amanda Peet), and a humorless nymphomaniac JAP (Claire Danes).

Igby is surrounded by wealth and opportunity, and burning with impotent desire to tear it all apart. But when he jumps off the train of privilege, he discovers that alienation is where you find it. He finds it most directly at home, where his domineering mother (Susan Sarandon) lectures him through a veil of booze and painkillers, while his "fascist" brother (Ryan Phillippe) scales the corporate ladder and his father (Bill Pullman) rots in a mental institution, a casualty of the same hypocrisy and vacuousness that drives Igby off the rails and into the heart of his greatest fear.

Writer/director Burr Steers, himself a scion of prep privilege, is clearly aware of the built-in resentment that accompanies such a character, and relishes the opportunity to watch him squirm. Igby is constantly getting smacked in the face, beaten with broom handles, sexually humiliated, and ridiculed for being such a scrawny little pisher. His only recourses are sarcasm, which he deploys masterfully, and the right of refusal to live up to his potential. The whole film builds up to the shattering of his every illusion.

That's what Holden Caulfield looks like, too. But unlike Holden--the inevitable comparison point for this character, despite a world of glaring dissimilarities--Igby's shell is thicker than his skull. His slide into despair is intentional. And that's what makes him interesting... even if he doesn't suffer all that much by blue-collar standards.