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 many for Kieran Culkin to show that he has a knack for playing an obnoxious youngest son from a wealthy family filled with members who are just as or even more obnoxious than he is. Obviously, he’s best known today as Roman Roy, the creepy, scummy, hilarious young son who you really can’t hate, on Succession. Heck, you could argue that, as the bed-wetting Fuller in Home Alone, he nailed the archetype in his very first movie part. But 20 years ago, Culkin truly solidified his place in my heart as the ur-shmucky sibling. Just as his older brother Macaulay was shying away from the spotlight, Kieran landed the titular role in Igby Goes Down, playing a cynical, aimless, unhappy teenager from an old-money family.
Igby Goes Down is one of those movies you could easily call a “cult classic,” since basically everything these days is described that way. (Writers love to think a movie they loved from a few decades back deserves a fresh look even when it maybe doesn’t, and especially when it’s way more popular than they realize.) But it feels like there’s something different with Igby—a film that most people I talk to who saw it around its release tend to love. Its legacy isn’t so much tied to its performance at the box office ($7 million on a $9 million budget), or whether or not Criterion is going to re-release it on Blu-Ray (it won’t). Instead, Igby is worth celebrating because it’s one of the all-time great documents of fictional rich people looking great and acting awful.
But 20 years later, Igby Goes Down is one of those films that has aged exactly how you’d want it to. Set in New York City at the start 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 the Dandy Warhols. (Watching the movie, you feel like you might catch a young Julian Casablancas staggering out of a bar.) The cast, too, has proven impeccable with time: you’ve got cuddly, loveable old Jeff Goldblum, today’s weirdo, sexy grandpa, playing a terrible rich guy. Claire Danes is a bored, young Manhattanite named Sookie Sapperstein. Ryan Phillippe, a few years removed from playing his own shitty rich kid in 1999’s Cruel Intentions, is Igby’s brother. The late writer Gore Vidal plays a priest. And at the heart of it all, there’s Culkin in his prep school rebel look of chinos, navy blazer, and Chuck Taylors. He acts like a little shit, but he’s a kid in a world filled with adults who act even shittier. What do you expect?