“Kissing Jessica Stein,” a romantic comedy about the relationship that springs up when a New York career girl frustrated by the dating scene answers a “women seeking women” classified, began life as a 1997 off-Broadway play called “Lipschtick.” The author-stars, Jennifer Westfeldt and Heather Juergensen, had met at a workshop and decided to write a piece for themselves based on their own experiences trying to meet the right men. The play was well-received, and the duo decided to use it as the basis for a screenplay, which was quickly optioned by Gramercy Pictures. The studio planned to rework the script as a starring vehicle for Westfeldt and Juergensen, and the young actresses seemed on top of the world. What happened next is almost a textbook example of how so many pictures never get made.
“It was exciting for us,” Juergensen recalled during a recent Dallas interview. “It was written up in the trades, and it was very official, and we were attached to star.” Westfeldt continued: “People said that’s impossible, and then of course it was a little bit impossible, because we probably would have been ninety by the time they made it. They got bought and sold four times while we were there. It was constantly changing ownership. And beyond that, what we found was that the studio wanted a more mainstream film than we were comfortable with, and the director [signed for the project] wanted a pure arthouse movie and wanted to get rid of all the mainstream comedic elements that we also wanted. So at the end of the day we thought there was a third movie there that we wanted to make,” one that would have the edginess of an independent film but also elements that would appeal to a mainstream audience. The studio argued, however, that such a combination would alienate both audiences–something disproved, in the writers’ view, by the success of pictures like “The Full Monty.” (“They love to crow about it when it works,” Juergensen noted, “but when you’re trying to do it, it’s easier said than done.”) The upshot was that Westfeldt and Juergensen decided to retrieve their rights to the script by buying it in turnaround and make the film themselves.
That proved a considerable difficulty, though, because of the stance the studio took. “They could have made it easier on us,” Juergensen said. “Unfortunately, there was a blanket policy at the time at the studio, that anything on their slate they were going to charge through the nose to get your rights back.” It was, as Westfeldt described it, “a David-and-Goliath story,” but eventually the studio was persuaded to sell the rights back for $750,000, to be paid after the actual investors in the finished picture had gotten their shares back.
Then came what Westfeldt and Juergensen called the worst part of making “Kissing Jessica Stein.” It was “getting the money,” Westfeldt said, to which Juergensen added that the effort was “absolutely, positively the hardest, the worst. We’re still bruised from that process.” They sought help, Juergensen noted, from “family, friends–everyone we’ve ever known.” They held readings for prospective investors and sold units in the project for $2500, described by Westfeldt as “a hefty sum for most people.” Juergensen wryly noted: “It’s so objectively a bad investment–two unknown actors in an independent film. Most people will say you might as well shred your money.” Westfeldt interjected: “We were trying to convince people we’re going to be the exception–your money is in good hands here.” Juergensen explained: “It was tough because we really believed in the story and in ourselves, and it seemed like audiences did, too. When people came to the play, or to these readings we would hold, people responded to the characters, they seemed to like the premise and going on this tremendous ride with us. That was frustrating–we had to combat the nay-saying” from the Hollywood types about how the project was doomed to fail.
Ultimately, however, Brad Zions, an America Online veteran who had founded a production company called Breakout Pictures, made a major investment in the project, and was joined by independent producer Eden H. Wurmfeld (and a host of small contributors). Charles Herman- Wurmfeld signed on to direct his first feature, and “Kissing Jessica Stein” was shot on location in a mere twenty-two days in 2000, with family, friends and acquaintances contributing along the way both on screen and off. The picture was then booked into the 2001 Los Angeles Film Festival, where it won the Audience Award and a Special Jury Prize and caught the attention of executives at Fox Searchlight Pictures. The company’s marketing head, Westfeldt said, made it “her crusade to get this film bought by them.” And to the surprise of both writers, Fox wanted to distribute “Jessica Stein” without changes: “We’d like to release the film literally as is,” Westfeldt remembered, not without a tone of amazement, that a studio executive said at their first meeting. Juergensen added that Fox Searchlight was doing “a stellar job of marketing it.”
Of course, any film that deals in any way with the subject of lesbianism may meet some resistance, and “Kissing Jessica Stein” is even more complex because the characters don’t simply wind up in a blissful relationship; as a result it could alienate some gay viewers, too. But Westfeldt and Juergensen have been very pleased with the reaction that far. “Ultimately the movie’s about tolerance,” Westfeldt noted, “not judging either of two truths and acknowledging both of them. Our writers’ response was to put the arguments about the issues in the mouths of our characters. All of the points of view are heard in the film, and I don’t think any of them are judged.” Juergensen added: “As writers we were telling a story about two people, and we didn’t have an agenda ourselves. We had to always be truthful to the characters.” Westfeldt continued: “I guess we always thought we might alienate the far left and the far right, and might get everybody else in between.” She described inviting an elderly landlady of hers to a screening, without thinking that the movie might offend her. When the leads first kissed, Juergensen heard the woman exclaim: “Oh, my God, that’s disgusting!” But afterward the woman approached Westfeldt and told her, “That was a beautiful movie!” The incident led Westfeldt to a general conclusion: “If this movie succeeds at all, people might leave with a slightly altered perspective.”