In a better movie world, filmmakers like Amy Heckering would constitute the backbone of the industry. Heckerling doesn't have a colossal artistic reputation or rack up Academy Award nominations. She's a mainstream, commercial director, and some of her hits, such as Look Who's Talking and its sequel and National Lampoon's European Vacation, are pure, unapologetic hackwork. But she's intelligent and talented, with a special, sensitive feeling for the comedy of adolescent romantic confusion, and at least twice, in Fast Times at Ridgemont High and Clueless, she's plowed those qualities into modest-seeming projects that have taken on the status of modern classics. But Clueless came out more than a dozen years ago, and since then, Heckerling has only managed to get one new movie into theaters, the sweet but underbaked Loser (2000). Heckerling has spent much of the time since then working on a comedy called I Could Never Be Your Woman. Heckerling wrote the script back in 1999, drawing on what she knows herself about the difficulties that women — especially women who aren't as young as they used to be — face in Hollywood. The movie stars Michelle Pfeiffer as a fortysomething TV producer with career problems, single-mother problems, and a confusing, budding romance with a younger man — Paul Rudd, who got his big break playing Alicia Silverstone's love interest in Clueless. (For Woman, Heckerling cast the then-unknown young actress Saoirse Ronan as Pfeiffer's daughter; Ronan has since won an Oscar nomination for her work in Atonement.) After years of delays, the movie is finally being released on DVD on February 12. In a story in Entertainment Weekly (not available on-line), Missy Schwartz writes that the movie's path to direct DVD release comes only "after coming this close to a theatrical release more times than Heckerling can remember" and terms the situation "something of a sub-cultural curio. It's a modestly budgeted indie that, while far from perfect, never got the chance it deserved, hitting every speed bump and knocking over every traffic cone along the way."

Initially Heckerling was going to make the movie for Paramount, but the project never got off the ground there, something that Heckerling believes had at least something to do with "concern about doing a movie with an older female protagonist — not anybody's favorite demographic." Heckerling then secured financing from Philippe Martinez, a controversial figure who, in 2005, set up Bauer Martinez Entertainment, which he promised to turn into the biggest indie film studio in the U.S. Martinez did allow Heckerling to get the movie made, though not without some odd compromises: for financial reasons, she was obliged to shoot the film in London and try to pass it off as Los Angeles. And by the time the film was completed, Martinez had decided that, contrary to his original plans, his company wasn't up to distributing its own movies. A distribution deal with MGM fell through, and other interested parties backed off after discovering that the DVD and non-pay-TV rights had already been signed away to The Weinstein Company, a move that Heckerling likens to saying, "Here, but my baby. I've cut its legs off, but it's still cute." Is Heckerling at least happy that her baby will be available to be seen now? She doesn't seem unhappy. Well, she doesn't seem miserable about it. But, at fifty-three, she isn't even promising that she'll direct again. "I don't want to work for the hell of it," she says.