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?
As a rich-dicks text, Igby has plenty of company. This is a rich category, filled with titles that often take time to be recognized as classics—a long-churning appreciation that I think we can chalk up to the films being pleasurable while their characters are mostly execrable. Take Brian De Palma’s 1990 adaptation of Tom Wolfe’s Bonfire of the Vanities, the absolutely calamitous production of which was chronicled by journalist Julie Salamon in The Devil’s Candy. That movie is still perhaps the example of a big ‘80s flop—Variety called it a “strained social farce” and Joel Siegel said, “This is not just a bad movie, this is a failure of epic proportions.” But I have always unapologetically loved it—not necessarily as a Wolfe adaptation or a De Palma film (two people whose work I admire), but for what it is: a movie about shitty rich people.
A big part of the problem, as many critics pointed out, was that Bonfire didn’t really offer up any sympathetic characters, even though the lead role was played by Tom Hanks. But even when I was younger, I remember thinking that not having to be sympathetic toward the characters was what made me like the movie. It was one of the first times I recognized that unlikeable characters are often the best kind.
Over 30 years after Bonfire came out in theaters, we’re still arguing about art about characters that aren’t nice. One end-around of the problem is: just make your unlikeable characters rich. Sometimes it works from the jump (author Kevin Kwan has shown how to strike a great balance with his mega-successful Crazy Rich Asians books); other times it requires more of a slow burn (Wes Anderson was an indie darling before everybody wanted to dress like a Tenenbaum kid).
But Igby Goes Down has always been a hard one to categorize. While it didn’t do well at the box office, the critics seemed to like it: Roger Ebert gave it 3 ½ stars and called it a “fresh” take on the what seemed to be the course material: The Catcher in the Rye. The New York Times review stated, “Ultimately, it gets at something that no other recent American movie has captured quite so acutely: a resentful, lurking disappointment in the good life.” And while Culkin and co-star Susan Sarandon both scored Golden Globe nominations for their efforts, the movie just never seemed to catch that needed spark.
Igby came out almost exactly a year after 9/11, and ended up being one of the last films to include the Twin Towers; perhaps maybe people just weren’t looking for “disappointment” and cynicism. They wanted heroes. And, anyway, the grand IP-ification of Hollywood was by then well underway. What did well at the box office in 2002? Spider-Man, Star Wars: Episode II - Attack of the Clones, and the second installment in the Harry Potter series. If ever there was a year that “got us to where we are today,” the year Igby came out feels like a logical pick. I’m not saying that to get into a Martin Scorsese comic book adaptations “aren’t cinema” discussion. I’m just stating the fact that the deck was already stacked against a movie like Igby.
But that’s sort of the funny thing about the books and movies about rich people and their problems. Sometimes it just takes a little longer for us to appreciate them. Maybe that’s because the rich of yesteryear just seem a little more quaint than the current crop. But if there was ever a perfect time for Igby Goes Down to be formally introduced into the canon of great works about the horrible rich, it’s right now.