Filmmaker Gary Winick died on Sunday at the age of 49. While in recent years he was known for his work on larger movies like 13 Going On 30 and Bride Wars , we’ve always been partial to his breakthrough film: an indie comedy from 2002 called Tadpole. The premise is simple: Oscar Grubman, a 15-year old preppie with an ancient soul (think Max Fischer), has a crush on his oblivious stepmother, Eve. But because the film is set in the affluent social circles of the Upper West Side, our protagonist likes to randomly speak in French and quote Voltaire; when characters fight, the heated exchange takes place over a game of tennis; and a romance between an adult woman and a young boy seems plausible rather than illegal. It’s a very adult world for a teenager to inhabit, and one that has only been captured a handful of times on film. Click though as we revisit some of our favorite examples.
Manhattan (1979)
While Isaac’s 17-year-old girlfriend Tracy doesn’t have as much screen time in the film as we’d like (thanks to the introduction of Mary, his best friend’s brainy mistress), in many ways her uptown earnest schoolgirl is the perfect preppie prototype — albeit much sweeter than some of the characters she likely spawned. In the end, she’s the only one of the characters in Woody Allen’s movie with a good head on her shoulders; as Tracy heads off to London she tells an inconsolable Isaac, “Six months isn’t so long. Not everybody gets corrupted. You have to have a little faith in people.”
Metropolitan (1990)
Whit Stillman’s comedy of manners — which was inspired by the filmmaker’s own experiences returning home during his freshman year at Harvard — offered what at the time was a rare glimpse into the lives of Manhattan’s Upper East Siders, a world full of complicated social mores and debutante balls. While the “Sally Fowler Rat Pack” is a good deal more austere than Blair Waldorf and the rest of the Gossip Girl gang, their romantic triangles are every bit as intense and complicated; you can’t ignore the influence Metropolitan had on GG — and just about any story about rich young people in NYC that followed it.
Cruel Intentions (1999)
This twisted teen drama, based on the 18th century French novel Les Liaisons dangereuses, appropriates all of the manipulation, seduction, and revenge of the original story, and sets the very adult action amidst a group of privileged New York City kids. At the time, Ernest Hardy of LA Weekly criticized the film saying, “In truth, the only reason this film was made was to allow viewers to ogle pretty young things behaving badly.” Isn’t it weird to think that there was once a point when that wasn’t a given in pop culture?
Igby Goes Down (2002)
Unlike previous films in the NYC rich kid genre, Igby Goes Down focused on life below 14th Street, reveling in a world of converted lofts instead of classic sixes. It’s also different in that Igby, the Holden Caulfield-inspired protagonist, is an insider looking for an out; he wants nothing more than to escape his phony family, and by extension, the world of privilege that he has been brought up in, rebelling against what is expected of him at every opportunity.
Tadpole (2002)
A recurring theme in many of these films: The tendency for sexual relationships to affect familial ones. In Cruel Intentions, Kathryn makes a bet with her stepbrother, Sebastian, that he won’t be able to sleep with the new virgin in town. If he manages to score, she agrees to have sex with him too. In Igby Goes Down, Sookie, Igby’s terminally bored liberal arts college lover, decides to ditch him for his older brother. It could be said that at least Tadpole goes the more traditional route, but then the movie totally jumps the shark when Oscar ends up sleeping with Eve’s best friend, Diane — mostly because she’s wearing his stepmother’s scarf — and his parents end up finding out about the tryst.
Born Rich (2003)
In our current Real Housewives-saturated culture, the idea of getting unlimited access into the lives of the disgustingly rich might not seem that novel, but when Jamie Johnson’s 2003 documentary debuted, it provided a unique — if inherently biased — glimpse into the world wealth and privilege. Whether there’s something interesting to be gleaned here or it’s just the self indulgent vanity project of a 20-something kid with way too much time and money on his hands is your call.
Twelve (2010)
On the surface, Twelve had a lot going for it: It was based on a critically-acclaimed novel of the same name by Nick McDonnell, who was only 17 when he penned his story about drugs and decadence on the Upper East Side. It starred a teen heartthrob, Chace Crawford of Gossip Girl fame (and 50 Cent!). It was produced by none other than Joel Schumacher. And yet, it’s probably the worst of the films to make our list.
Is this a sign of the decline of the NYC prep narrative — at least on the big screen? While we see why the whole “poor” rich kid trope makes better film fodder than a celebration of excess, in the current economic environment, do audiences really want to be manipulated into feeling sorry for their much wealthier fictional counterparts? Let us know what you think, what films we left out, in the comments.