We spoke with Boondocks Film Society co-founders Cindy Heslin and Jeff Palfini about their unique pop-up film event series, created with collaborators David Ruchman, Rufus de Rham, and Alix Diaconis.
Boondocks hosts monthly film events across northwest Connecticut, the Hudson Valley, and the Berkshires, often in unexpected venues. Each screening is carefully themed around a chosen film to create an immersive, one-of-a-kind experience.
1. What kind of film events do you produce?
Jeff Palfini: We build themed events around rep-house films. Each screening includes a Happy Hour, with music by local musicians, film-inspired food from area chefs, themed cocktails, and sometimes a Q&A with someone connected to the film. Plus, guests can take home an artist-designed commemorative poster.
2. What inspired you to start Boondocks?
Cindy Heslin: We used to attend a curated film series at the Castro Theatre in San Francisco called Midnites for Maniacs. It showed unexpected double or triple features that took on new meaning with an audience. That experience really stuck with us.
JP: Our personalities were shaped by rep-house programming. We’ve spent countless nights fueled by popcorn and Sprite, discovering what aged well—and what didn’t.
CH: Boondocks was born the moment we stepped into the Colonial Theatre in North Canaan in early 2017.
3. Do you come from film backgrounds?
JP: Not professionally, but we’ve spent so much time in theaters. Soundtracks introduced us to some of our favorite bands. Movies have shaped our sense of humor, style, and creativity.
CH: Boondocks is about more than film. The Happy Hour builds community. People discover new venues, bands, chefs, bartenders, and artists—all tied together by a movie we love.
4. How do you choose your films and themes?
CH: Sometimes the venue drives the choice. When we screened Porco Rosso at the Great Barrington Airport, we had real planes on-site. Other times, we start with a chef or band we want to work with, and find a film that suits their vibe.
JP: We tend to highlight underappreciated movies, especially from the ’90s, and stories about people on the fringes.
5. What’s the most rewarding part?
JP: Those unexpected magic moments—like a moving Q&A, or when the moon rises during an outdoor screening.
CH: We’ve met so many interesting and creative people through Boondocks. Some have become dear friends.
6. Since this is our food issue, what are your favorite food-related film scenes?
CH: Tampopo—especially the surreal scenes between the gangster and his girlfriend. They’re sexy, funny, and utterly strange. And of course, the food in every Studio Ghibli movie is unforgettable.
JP: The scene in Daisies where the girls dance across a feast table. It’s rebellious and chaotic—a punk rock kind of decadence.
CH: The breakfast scene in Big Night is quietly profound. No dialogue, just the act of feeding someone you love. When we screened it, the flipping of the timpano pan was a moment of pure joy.
JP: Honorable mentions: the opening of American Psycho and the mozzarella in carrozza in Bicycle Thieves.
7. Dream film event?
CH: We’d love to screen something on a lake, or in this overgrown abandoned pool near Jeff’s house. We’re always up for making things beautifully complicated.
Keep an eye on boondocksfilmsociety.org and their socials to see what’s planned for this summer and fall.