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INTERVIEW: "The Preppie Connection" Filmmaker Joseph Castelo On The Film’s Talented Young Cast And The Need To Fit In

Nicole Barylski

Thomas Mann stars as Toby Hammel in "The Preppie Connection." (Courtesy Photo)

"I can't think of a better place to premiere this film than the Hamptons," filmmaker Joseph Castelo told Hamptons.com about the debut of his latest project, "The Preppie Connection."

Makings its world premiere at this year's Hamptons International Film Festival (HIFF), "The Preppie Connection" follows the exploits of Toby Hammel (Thomas Mann), a teenager from a working class family who is thrust into the world of the privileged when he is awarded a scholarship to Sage Hall, a prep school located in his hometown. In a desperate effort to fit in amongst his peers and win the affection of his dream girl, Hammel realizes the easiest way into their inner circle is to supply them with drugs and manages to smuggle $300,000 of uncut cocaine into the United States.

We caught up with Castelo before the film's premiere to discuss growing up in the 80s, the scandal that rocked prep schools nationwide, and the talented young cast of "The Preppie Connection," which stars Thomas Mann, Lucy Fry, Sam Page, Logan Huffman, Bill Sage, Amy Hargreaves, and Jessica Rothe.

Is this your first time at HIFF?

It's my second time as a filmmaker. I premiered a film ["American Saint"] there in 2001 while I was in film school that won the festival, so I really love the Hamptons International Film Festival. I'm looking forward to coming back to the Hamptons, but also to reuniting with the cast.

The film's based on a true story, so was the story something you followed when it actually happened?

I went to boarding school in the 80s, and I'd heard about this story. It just sort of disappeared off the radar but I'd never lost interest or fascination with the story. I went and did research on it, secured the rights to it, and for me, it's a very personal film, it's a very personal story, in that I related my own experiences in boarding school to the central character's experiences. It really was a cathartic experience making the film.

Is the film pretty true to the actual story or did you add some of your own personal experiences to it?

It's both. I built the world up from my experiences at boarding school in the 80s, but we stayed close to the story and what actually happens. Because of my agreement, I had to keep some distance from the actual story itself, but for the most part it stays true to the story.

Were you able to speak to any of the actual people involved in the story?

Yes. I spoke to the person involved in the scandal.

What was the casting process like?

I did the casting with S2 Casting. Thomas Mann actually sought out the film and sought me out, and really wanted to be a part of it, which was so exciting. He was so committed to the project, and that means so much to me as a director to have committed cast members. Lucy Fry was the exact same. She sought the project out and we actually met over Skype at first and we just hit it off. The casting was just something that came together beautifully because I met such great people and people I wanted to make the film with.

The cast was great. Thomas was perfect for the role.

He's amazing. I keep saying it; he's such a smart actor. He's always processing information through his character's filter and you can see it and he's so subtle. Just the slightest expression lets you know what's inside the character and it's just such a gift. When you're shooting and you can see that, but particularly when you're cutting the material, it's such a gift to have an actor that's that subtle and has such a range. He's an old soul.

It seems like the theme of the film is "us versus them," something that's still so relevant nowadays. Is that one of the reasons you felt the timing was right to make this film?

It's funny how films sort of synchronize with current events and current issues. I think the film is connected to the zeitgeist in that way. The issues around the disparity of wealth and the 1 percent and the 99 percent are actually all relevant to "Preppie." The timing wasn't necessarily conscious on my part, but it definitely lines up with issues that are relevant today.

The need to fit in is something that will also always be relevant.

The character is an outside and that's something that I identified with. For me personally, when I went to boarding school I experienced culture shock. That was something that was really important to me for the character, that you got the sense that he was actually shocked by this environment that he was thrust into and that's something that I experienced when I went to school. I felt very personally connected to Toby. We talked a lot about the costuming, the fashion in the film. Everything that they [the characters] had was handed down to them. At that time, a lot of the kids wore clothes that were handed down to them generationally, so they'd have their dad's tweed blazer or their grandpa's overcoat or something passed down from their mother or grandmother. It wasn't something that you could buy. Everything now you can go into a store and create any kind of identity you want from fashion, in a retail environment. At that time, it wasn't something that could be purchased. There was no access to that circle. It was even harder to fit in and Toby figures out that cocaine is the shortcut into the circle.

Is there anything else you'd like to add?

Music is really important to the film. We had a great score composed by Sam Bisbee. One of the things we were aiming for was to find songs that weren't immediately familiar to people when they associate with the 80s. I think we achieved that. We found some really cool, sort of B-side songs that were alternative at the time, covered by modern bands. There's a really cool band that covers some songs called Future Punx, they're actually playing in the Vanity Fair clip.

"The Preppie Connection" is screening at the Regal East Hampton Cinema UA (30 Main Street, East Hampton) on Saturday, October 10th at 5:15 p.m., and again at the Regal East Hampton Cinema on Sunday, October 11th at 8:30 p.m.

For more information about the Hamptons International Film Festival, visit hamptonsfilmfest.org. For more information about "The Preppie Connection," visit coalitionfilms.com.


Nicole is the Editor-in-Chief of Hamptons.com where she focuses on lifestyle, nightlife, and mixology. She grew up in the Hamptons and currently resides in Water Mill. www.hamptons.com NicoleBarylski NicoleBarylski




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