Allen sets his two tales as stories within a framing device. A group of friends are having dinner, two of whom are successful playwrights. Max (Larry Pine) believes in the seriousness of life and is known for his dramas. Sy (Wallace Shawn -- the inside joke is how this setup plays off Shawn's role in My Dinner With Andre) thinks life is absurd and is known for his comedies. Like Mel Brooks, who can stare down the evil of the Holocaust and produce Springtime for Hitler, Sy spots the core elements of humor in every painful human situation. A third diner, Jack (Matt Servitto), proposes an impromptu contest. He tells of some friends who are having a dinner party when an unexpected guest arrives and has to be dealt with by the hosts. Is this the beginning of a tragedy or comedy? Max and Sy rise to the challenge and begin to spin out alternate stories, each of which is dramatized and intercut, a strategy more effectively executed in Peter Howitt's Sliding Doors.
Several elements are common to both tales. The unexpected guest is the titular Melinda (Radha Mitchell) who arrives in distress over a failed marriage and becomes the object of the other characters' efforts to find her a new man. In Max's account the dinner party is hosted by an idle rich woman named Laurel (Chloe Sevigny) and her philandering, would-be actor husband Lee (Jonny Lee Miller). Sy's hosts are an independent filmmaker named Susan (Amanda Peet) and her out-of-work actor husband Hobie (Will Ferrell). Max's Melinda was once married to a wealthy doctor she cuckolded in a torrid but short-term and ultimately violent affair with a photographer. Now Melinda pines for her old life and her two children the courts have barred her from even visiting. In Sy's narrative, it was Melinda's husband who was unfaithful, and they were childless. Not even Sy wants to try to extract laughs out of infidelity when there are children involved.
This set-up leads to predictably divergent resolutions. And along the way we revisit themes Allen has worried over throughout his prolific four-decade career as a filmmaker. Can love endure? Does love provide a refuge from the meaninglessness of life? What strictures on our behavior ought we to honor? What may we decently sacrifice in responding to love's summons? Why does the physical element of romantic love inevitably lose the heat of urgency? What replaces diminished physical passion? Are there conditions under which infidelity is defensible? When is infidelity forgivable? And in the face of inevitable death, not just of the individual human being, but of the very planet on which we live, how do we choose what to do and what not to do? In short, does anything matter? Many of these issues quickly become theological in nature, and though Allen has wrestled with theological concerns in the past, most notably in Crimes and Misdemeanors, he does not do so here, and that's a weakness the film doesn't overcome.
Since Woody Allen movies no longer do much box office (his films used to open in the major complexes but now are usually relegated to art houses), one might wonder how he still manages to get his pictures financed and released. There are several answers. First, he is still able to make the films he likes because he keeps costs low and gets very capable casts to perform for scale. Actors like to work with him because of the prestige, and he writes parts that win Oscars and other award nominations. More important, even though he's become a minor figure in today's American cinema, he has a loyal fan base worldwide. In Europe, he's considered a genius. Fans of his work like me have seen every film Allen has made. And we go to see his new pictures even if we didn't much like his last one. We know his canon, and we know that he's made great films in the 1970s, '80s, '90s. Maybe the new one will be the next great one. So the talk among Allen fans is always how the current film stacks up against the rest. Here's my verdict on Melinda and Melinda: It's the best Allen film since 1999's Sweet and Lowdown, but the drama is inadequately affecting, and the comedy isn't funny enough to lift this picture out of the middle tier. Alas. On the other hand, his next film Match Point is already in post production.