Heckerling relied closely on the creative talents of long-time friends and associates Rob Hahn (director of photography), Steven Jordan (production designer), Mona May (costume designer), and Debra Chiate (editor) to bring the Loser to the screen. Jordan and May previously worked with Heckerling on Clueless and A Night at the Roxbury; Chiate edited Clueless, Look Who’s Talking and Look Who’s Talking Too, as well as a number of Heckerling’s AFI student films; and Heckerling’s relationship with Hahn dates back to NYU Film School where they worked on numerous award-winning short films together.
“The great thing about having been in this business for a while is that you wind up having relationships with people that you’ve worked with before, and a kind of shorthand develops which is great professionally and personally,” explains Heckerling. “I know that if I talk to Steven about a mood I feel and how that would translate into different colors, that he knows what I mean. And when I tell Mona what a character is like, I know she’s going to come back to me with clothes that will tell the audience who that character is.”
Many hours are spent in pre-production coming up with an overall vision for the film. As production designer Steven Jordan explains, “We sit down and talk about the characters and their relationships to the environment and eventually put together a palette that will be incorporated throughout the film from wardrobe to locations. Because Loser is set in New York at the beginning of the school year, we chose a palette based largely on the warm, autumnal colors prevalent in New York in the Fall.” Offers Jordan, “The catch phrase was ‘if you can see it in nature in the Fall, then it’s a good color for the picture.’ ”
Principal photography began November 3, 1999 in New York City where the company filmed key exterior scenes in such locations as Times Square, Washington Square Park, Greenwich Village, Soho and Grand Central Station over a five-day period. In terms of selecting locations, it was important to the filmmakers to establish a look and feel for the movie that unmistakably represented the urban aesthetic of New York. “There is only one New York,” emphasizes Jordan. “You can build the interior of a New York apartment on a soundstage and it will translate just fine on screen, but when you’re looking to replicate the look and feel of the theater district on a Saturday night you can’t do Times Square anywhere but Times Square.”
Production shifted to Toronto on November 13, where a soundstage provided the space for several interior sets including the university dorm, Professor Alcott’s apartment, and the veterinary clinic where Paul is forced to take residence when his roommates have him evicted from the dorm. Custom backdrops were created to provide scenic New York views from the windows of the dorm and veterinary clinic.
Jordan acknowledges that one of the most important elements of his job is creating an environment so the actors can forget they’re on a set. “You need to create a space that makes it feel like it’s theirs, like they’re at home.” explains the designer. “You never want them to think or be conscious of the fact that they’re on a set. For me, part of the process is to involve them early on in pre-production, to welcome any ideas they come forward with. In a lot of cases, something as seemingly inconsequential as a toy or a little vase can stimulate something for an actor that will help to solidify his performance and character development so it’s beneficial for all to bring them into the process.”
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