In celebration of LGBTQ pride and in honor of its 20th anniversary, the creators and cast of “Kissing Jessica Stein” reflect on the indie film's legacy.
They didn’t know it right away, but when Heather Juergensen and Jennifer Westfeldt met at a New York theater retreat in the late ‘90s, it was kismet.
After a brief stint in Los Angeles, Westfeldt missed theater and New York so she moved back. Upon arriving, she called Heather, telling her,"‘Remember me from the summer? We said the thing about the theater? Let’s do it.” That concept became “Kissing Jessica Stein,” a film about two women who explore a relationship with each other, after being exhausted by New York’s male dating pool. The titular character, played by Westfeldt, is a neurotic copy editor who is held back, romantically and artistically, by her perfectionist standards. That’s until a personal ad placed by a free-spirited gallerist named Helen, played by Jeurgensen, piques her interest.
At first, they sold shares, valued at $2,500 each, to anyone who could buy one — or even a half of one. Then they found an angel investor, who fronted a large portion of the film’s modest budget. By that time, they had signed on friends in major behind-the-scenes roles, including Eden Wurmfeld, as executive producer, and Lawrence Sher, as cinematographer.
After approaching and being turned down by more experienced directors, Juergensen and Westfeldt settled on the enthusiastic, green director, who had recently moved to LA to pursue a career in film after working in theater in San Francisco. When Herman-Wurmfeld came across the script, he was crashing on his sister’s couch, working a job at a cafe, and making his way around the car-polluted city via bicycle.
Once Juergensen and Westfeldt made their choice of director, the cast was rounded out with a few, more well-known faces, including Scott Cohen, who plays Jessica’s former boyfriend and current boss Josh, and Tovah Feldshuh, who plays Jessica’s somewhat overbearing Jewish mother. “What’s wonderful about it is that there’s an arc to his character. You get to see where he starts and what he becomes and what he’s missing,” Cohen said.
“Strangers come up to me on the plane, or in line for something, and say, ‘That scene really changed my life’ or ‘That was the scene I showed my parents,’” Westfeldt said, describing experiences both she and Jeurgensen still have. “For people who didn’t have the luxury of coming from a supportive family or a supportive, liberal place, it’s been a touchstone.
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