While Woody Allen has long fused comedy and drama in his films, he embraces the two styles in a new and unusual way in this feature. Sy (Wallace Shawn) is enjoying dinner with some friends when they begin debating the nature of the tragic and the humorous. Sy, observing that a very fine line separates the two, decides to demonstrate this notion by showing how the same essential story can be either funny or sad depending on the way certain elements are handled; for the rest of the film, we jump back and forth between two versions of the story of Melinda (Radha Mitchell), a young woman with some serious problems in her life. In the tragic version, Melinda crashes a dinner party thrown by old friends Laurel (Chloë Sevigny) and Lee (Jonny Lee Miller). When she arrives, Melinda is distraught and under the influence of pills and alcohol, much to the annoyance of Lee, an actor hoping to impress a producer who is one of his guests. After a bad breakup with her husband, Melinda lost custody of her children and came to New York City, where she became involved with Ellis Moonsong (Chiwetel Ejiofor), a handsome and well-mannered composer whose promises to her proved to be worthless. Meanwhile, on the funny side of town, Melinda shows up dazed and confused at the home of Susan (Amanda Peet) and Hobie (Will Ferrell), who are in the midst of a dinner party. Learning about the sad state of Melinda's love life after divorcing her husband and losing custody of her children, Susan decides to play Cupid and fix her friend up with a well-to-do dentist. However, neither Susan nor Melinda are aware that there is another man deeply interested in the troubled divorcée -- Hobie. Melinda and Melinda also features Josh Brolin, Vinessa Shaw, and noted theatrical director Gene Saks.
by Mark Deming synopsis