Stephen Dest

Reel Estate

Stephen Dest sees New Haven as a city of artists and unpredictable characters. “This is a small city, a walkable city, an intelligent city. No matter where you go, you have the best conversations,” he says. “Two things you always notice about New Haven: there’s the artist and there’s the drifter. They could be retired professors, or they could be vagabonds. You can’t tell.”

What better place to make his first feature film, My Brother Jack? Dest is putting the finishing touches on the movie this week, just in time to submit it to festivals. The film was financed with private investors and through the Kickstarter fundraising website (which he’s tapping again for some post-production money).

Jack has both the artist and the drifter in it. Indeed, in Dest’s screenplay, they’re related—siblings who share a tragic past that has produced a present-day mystery. One brother is a painter. The other suffers from sleep paralysis. Dest plays their passions and problems off each other to explore the bonds of family and anxieties of modern existence.

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New Haven has been hearing about the movie for a few years now. There have been fundraising parties, filming sessions at local bars, parks and coffee shops, and screenings of the trailer. Local musician Jonny Rodgers (the Mighty Purple guitarist who now does avant-garde work with tuned wineglasses and tape loops) composed the soundtrack.

“All the locations are in New Haven,” Dest says over coffee at Woodland on Orange Street. “We shot at the Taft Apartments, the Owl Shop, in alleys on Audubon Street, at the Little Theater, at the Kehler Liddell Gallery…” For cinematic purposes, Dest turned the distinctive Diesel on State Street into “the perfect nebulous New Haven bar.”

The most important and stable location for the shoot was the UpCrown Production Studio on the second floor of LoRicco Towers on the club-hopping block of Crown Street between Temple and Orange. Jack is the biggest project yet for the fledgling media facility.

And, it seems clear, for Dest. His background is mostly in theater, and he runs the drama program at Neighborhood Music School on Audubon Street. He’s also taught at Betsy Ross Arts Magnet School and regularly directs at local theaters such as Theatre West in West Haven.

Not unlike Dest’s transition from being an actor in touring plays and musicals to being a husband and father with a more settled existence in New Haven, he is now gradually switching from stage to film because he likes the more leisurely pace of putting a project together and the permanence of the finished project. He dabbled in documentaries for a while, then adapted a play he’d written into the highly personal short film Blind, which earned a screening at the Cannes Film Festival in France and helped garner interest in My Brother Jack.

Dest’s positive and professional experience making movies in New Haven prompts questions about why more people don’t do it. Some of the crew who worked on the project came from Los Angeles and were amazed at the ease of finding locations. “You should be making a movie a month here,” they told Dest. “You should be filming every hour.”

Dest didn’t take the accessibility, generosity and flexibility of his cast, crew and location-providers for granted. Unlike a lot of indie film productions, he insisted on paying everybody involved a little something—even in a couple of cases where he was offered services for free. “Everyone got paid,” Dest says proudly. “Temple Grill catered. I commissioned the art I used from the artists. I wanted to put people to work.”

While New Haven will be regularly recognizable in the movie (which has yet to be screened in its complete form), Dest says his characters don’t mention it much. For his purposes, “it seems more natural to say, ‘It’s the guy from town.’ Visually, you know it’s New Haven. After the fact, you can worry, ‘Am I being too familiar?’ You kind of want that universal quality.” To that end, though the film captures “many iconic New Haven locations,” Dest largely avoided the distinctive presence of Yale University.

The story of Jack is about “two brothers witness their parents being murdered.” Two decades later, the man convicted for the murder gets released and is killed himself. The question, then, is: “Who killed the killer?” Meanwhile, the story behind the film is one of community, collaboration and common artistic goals. It’s about happy coincidences and hard work.

“The whole city was involved in some way or another. I was just not prepared for how open everyone was going to be,” Dest recalls wistfully, now that the remaining work on the film has been relegated to an isolated editing room. “We could totally do this again. What’s necessary is getting the right people involved.”

And the right city.

Written and photographed by Christopher Arnott.

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