Is there anyone more hateable than a prep school kid? The smug sense of entitlement, the class privilege worn as casually as a popped-collar polo, the comfort in the knowledge that they are better than you simply by dint of birthright.
Are all those who pass through the hallowed corridors of an elite boarding school really so insufferable? Probably not. But pop culture has trained us to hate these people, and given that, for many of us, firsthand experience with these divine creatures is limited to the likes of George W. Bush and Mitt Romney, it’s only too easy to oblige.
Director Joseph Castelo’s “The Preppie Connection,” inspired by the true story of a prep school kid arrested for trafficking cocaine from Colombia in the 1980s, treats prep school kids with all the subtlety of an ‘80s slobs-vs.-snobs comedy. These are entitled assholes with obnoxious haircuts who pass the time snorting coke on a golf course while they wait to get auto-admitted to Yale. Toby (Thomas Mann) is a working-class townie attending Sage Hall (a fictional boarding school standing in for Choate Rosemary Hall) on scholarship, and thus an outsider to the world of elite privilege. He becomes fascinated by the assholiest of the assholes at Sage, not least because among them is the gorgeous Alex (Lucy Fry). Toby ingratiates himself with the cool kids by selling them marijuana before hitting up his buddy Fidel (Guillermo Arribas), the son of the Colombian ambassador to the United States, to travel with him to Colombia where he can buy cocaine at the source. Thus, Toby, an awkward outcast, becomes the most powerful student at Sage Hall.
Castelo plays this all as a slow-burn thriller, leaning heavily on Sam Bisbee’s moody synth score to create an atmosphere of creeping dread even when the images are strictly off the shelf. Castelo aims for an air of cool detachment, an alienated style to match his disaffected characters, but his direction is a little too baggy and inconsistent to completely pull it off. Bouncy handheld shots sit uneasily beside icy long shots, and the result is a bit muddled. Castelo tells far more often than he shows. There is scarcely a thematic thread that is not at some point rendered overtly in dialogue or voice-over narration. The latter of these is also the delivery mechanism for much of the film’s plot information.
That’s not to say that the film isn’t compelling. For anyone who enjoys watching the young and overconfident get way in over their heads—e.g., fans of “Shattered Glass,” “Less Than Zero,” or “The Falcon and the Snowman”—”The Preppie Connection” certainly gets the job done. It’s just that it largely does so through borrowed images and a stock storyline. There is a tantalizing idea that Toby’s burgeoning drug business is a form of social climbing, an illicit means of gaining the same level of social and monetary capital as his fellow preppies. But, on a plot level, Castelo often draws Toby’s motivation too narrowly, as simply an opportunity to get closer to Alex.
In the end, this is a movie about class privilege, about the fundamental inequity of a system that treats one person better than another simply because he was born into the right family. If Castelo doesn’t always hit the bullseye, he at least trains his lens on the right target.