The Preppie Connection

How did kids scramble for acceptance before the internet? Joseph Castelo's The Preppie Connection posits that then, as now, you could get a lot of mileage from drugs. Its blasé narrator is Toby (Thomas Mann), a working-class kid in 1980s Connecticut who lands a scholarship to his hometown prep school and quickly falls in with a cadre of vain, supercilious youths, casting aside the straight-laced Colombian student, Fidel (Guillermo Arribas), who befriends him on the first day. Fidel later unknowingly facilitates Toby's first trip to Cartagena, which he visits with the sole purpose of scoring a refill of cocaine for his new friends. Despite his nervous fumbling ("Do you know where I could find … cocaína?"), Toby locates an enthusiastic supplier (Hemky Madera.)

That Toby is able to smuggle cocaine without Customs batting an eye is one of a few creative liberties in Castelo and Ashley Rudden's screenplay, which frequently emphasizes the irrational hormonal behavior underlying its conceit. Toby's school is a stand-in for the real-life Choate Rosemary Hall, which weathered a similar scandal in the early ‘80s (though that student flew to Venezuela, not Colombia -- a less likely destination now that audiences have seen so many movies referencing Pablo Escobar).

But with little time spent on developing these characters, Toby and co. come across as a pale, anti-intellectual imitation of the college-aged friends in Donna Tartt's The Secret History -- a novel that explores the roots of its characters' moral recklessness rather than just chalking it up to teenage feelings. Toby's eventual comeuppance feels as preordained and empty as the preppie/townie dichotomy regurgitated here from so many outdated teen-media artifacts.



  • Joseph Castelo


  • Thomas Mann
  • Lucy Fry
  • Logan Huffman
  • Sam Page
  • Bill Sage
  • Amy Hargreaves
  • Jessica Rothe
  • Robert Gorrie
  • Hemky Madera


  • Joseph Castelo
  • Ashley Rudden


  • Adam Folk
  • FA Eric Shultz
  • Joseph Mensch
  • Joseph Castelo
  • Charlie Bunting
  • Billy Raftery

Now Playing

The Preppie Connection is not showing in any theaters in the area.

What others are saying

  • Now Playing

    By Film...

    By Theater...