If not exactly a one-hit wonder, Amy Heckerling is certainly a mystery. After directing the highly successful "Fast Times at Ridgement High (1982) and writing/directing an excellent modern adaptation of Jane Austins's "Emma"- insert "Clueless" (1995) here - it appeared that she had a unique connection with both teenage viewers and those nostalgic about their teenage years.
Then she spectacularly crashed and burned with the appropriately named "Loser" (2000). That career breaker would be in the running for a "worst film of all time" designation, were it not for its modest scale. Nonetheless it exposed huge deficiencies in Heckerling's writing talents, acting for the camera directing skills, and basic judgment.
Six years and no films later she was finally able to cobble together another modest scale film "I Could Never Be Your Woman", which is much closer to "Loser" in concept and execution than to her successful films.
Heckerling is at heart an expressionistic movie-maker; a fine quality except that mainstream audiences, used to a steady diet of movie realism, sometimes just don't get it. Her two main successes were situations where the surreal stuff was an ironic undercurrent masked by a realistic facade. With "Loser" her elements went out of balance and she repeats this same mistake in the main storyline here; a blend of the Hollywood insider story Altman did so well in "The Player" and the standard Lifetime Channel exploration of female angst, aging, and discontent.
Fortunately there is parallel storyline involving the main character's middle school daughter, which allows Heckerling to get back to what she does best. And even more fortunate is the casting of newcomer Saoirse Ronan in this role. Ronan has since broken out with her Oscar nominated performance in "Atonement" (2007). "I Could Never Be You Woman" was her first feature film, which she easily steals. So much so that you are tempted to fast- forward through the scenes in which she is not present. Heckerling should have recognized what she had here and initiated major script revisions to amp up Ronan's screen time; especially more scenes of her playing off Paul Rudd (her mother's boyfriend) and Jon Lovitz (her father). Even so this will be become a minor cult classic on the strength of this one performance.
Michelle Pfeiffer and Paul Rudd (who played Cher's stepbrother in "Clueless") play the film's May-December romantic couple. Their chemistry is not bad and the romance is mostly played for its comic qualities. This stuff is good enough to keep and certainly not one of the film's fatal weaknesses. These can be found in some ill-conceived expressionistic elements: Tracey Ullman as an extremely boring Mother Nature, Fred Willard as an unfunny version of his Ron Albertson "Waiting for Guffman" (1996) character, and Sarah Alexander as a kind of concentration of all the irritating qualities of Jenny McCarthy. The one expressionistic element that does work is the "Head of the Class" style television show that Pfeiffer's character is producing; complete with tacky production design and middle age actors playing high school students.
The film might just be the highest-profile motion picture ever to take the direct-to-DVD route, due to bad financial practices rather than the marketability of the final product. Then again when you try to figure out the film's target audience you realize that it is even narrower than the standard "chick flick", and unlike Heckerling's hit films there is nothing here of interest to the teen demographic.
Rosie (Pfeiffer) is a middle age TV writer/producer whose once popular TV series needs a talent transfusion, and whose main occupation seems to be staying young. Adam (Rudd), a 28 year-old actor, is added to the cast and it is quickly apparent that he and Rosie are soul mates despite the age differential. Middle school daughter Izzie (Ronan) has a crush on a boy at her school and Rosie must adjust to her daughter growing up. As someone observed earlier, Izzie is a little like what "Juno" might have been four years before her pregnancy. Ronan's two songs (including a parody of Britney's "Oops" with altered lyrics) are the film's comedic highlights.
The DVD package is pretty basic; a few deleted scenes, the unused theatrical trailer, and an extremely lame commentary.
Then again, what do I know? I'm only a child.