‘Igby Goes Down’ is an underrated gem in the Rich People-Being-Awful genre

I don’t know how many roles it takes for an actor to be considered the best at what they do. Still, it didn’t take much for Kieran Culkin to show that he has a knack for playing the obnoxious youngest son of a wealthy family filled with members as or even more obnoxious than he is. He’s obviously best known today as Roman Roy, the creepy, creepy, hilarious young son who you really can’t hate, on Succession. Heck, you could argue that, as the bed-wetting Fuller enters Home alone, he established the archetype in his very first film part. But 20 years ago, Culkin really cemented his place in my heart as the quintessentially shmucky sibling. Just as his older brother Macaulay shied away from the limelight, Kieran landed the title role Igby goes downplays a cynical, aimless, unhappy teenager from a family with old money.

Igby goes down is one of those films that you can easily call a “cult classic”, since pretty much everything these days is described as such. (Writers love to think that a movie they loved from a few decades back deserves a fresh look, even when it might not, and especially when it’s way more popular than they realize.) But it feels as if there is something else involved Igby-a movie that most people I talk to who saw it around release tend to love it. Its legacy isn’t so much tied to its performance at the box office ($7 million on a $9 million budget) or whether Criterion will re-release it on Blu-Ray (it won’t). Instead, Igby is worth celebrating because it’s one of the all-time great docs about fictional rich people who look good and act horribly.

But 20 years later, Igby goes down is one of those movies that has aged exactly the way you want it to. Set in New York City at the beginning of the new century, it shows a Manhattan that was still a little grungy, filled with sexy junkies who could live in lofts in Soho. The soundtrack has a Makeout Club era, proto-indie sleaze feel with tracks by Badly Drawn Boy and Dandy Warhols. (Watching the film, you feel like you might be catching a young Julian Casablancas staggering out of a bar.) The cast has also proven impeccable over time: you’ve got the cute, lovable old Jeff Goldblum, the modern-day weirdo, sexy grandpa, plays a terribly rich guy. Claire Danes is a boring young Manhattanite named Sookie Sapperstein. Ryan Phillippe, a few years removed from playing his own shitty kid in the 1999s Evil intentions, is Igby’s brother. The late author Gore Vidal plays a priest. And at the heart of it all is Culkin in his prep school rebel look with chinos, navy blazer and Chuck Taylors. He acts like a little shit, but he’s a kid in a world full of adults who act even shittier. What did you expect?

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