The central plot features Block driving to a university from which he was once thrown out, in order to receive an honorary degree. Three passengers accompany him on the journey: a prostitute, a friend, and his son, whom he has kidnapped from his ex-wife. However, there are many flashbacks, segments taken from Block's writing, and interactions with his own fictional characters. Deconstructing Harry received moderately positive reviews from critics.
One night, Lucy (Judy Davis) gets a taxi to the home of author Harry Block (Woody Allen). She has just read Harry's latest novel. In the novel, the character Leslie (Julia Louis-Dreyfus) is having an affair with her sister's husband Ken (Richard Benjamin). Lucy is angry because the novel is patently based on her and Harry's own affair; as a result, everyone knows about it. Lucy pulls a gun out of her purse, saying she will kill herself. She then turns the gun on Harry and begins firing. She chases him out onto the roof. Harry insists that he has already been punished: his latest girlfriend Fay (Elisabeth Shue) has left him for his best friend Larry (Billy Crystal). To distract Lucy, Harry tells her a story he is currently writing: a semi-autobiographical story of a sex-obsessed young man named Harvey (Tobey Maguire) who is mistakenly claimed by Death.
In therapy, Harry realizes he has not changed since he was a sex-obsessed youth. Harry discusses the honoring ceremony at his old university, taking place the next day; he is particularly unhappy that he has nobody to share the occasion with. After the session, Harry asks his ex-wife Joan (Kirstie Alley) if he can take their son Hilliard (Eric Lloyd) to the ceremony. She refuses, stating that Harry is a bad influence on Hilliard. She is also furious at Harry for the novel he wrote. In it, the character Epstein (Stanley Tucci) marries Helen (Demi Moore), but the marriage begins to crumble after the birth of their son.
Harry runs into an acquaintance, Richard (Bob Balaban), who is worried about his health. After accompanying Richard to the hospital, Harry asks him to come to the university ceremony. Richard appears uninterested. Harry then goes to meet his ex-girlfriend Fay, who reveals that she is now engaged. Harry begs Fay to get back together with him. He asks Fay to accompany him to his ceremony, but it clashes with Fay's wedding, scheduled the following day.
That night, Harry sleeps with a prostitute, Cookie (Hazelle Goodman). Harry then asks Cookie to accompany him to his ceremony.
In the morning, Richard unexpectedly arrives to join Harry and Cookie on the journey. On a whim, Harry decides to "kidnap" his son Hilliard. Along the way, they stop at a carnival, then at Harry's half-sister Doris's (Caroline Aaron). Doris, a devoted Jew, is upset by Harry's portrayals of Judaism in his stories, as is her husband (Eric Bogosian). During the journey, Harry also encounters his fictional creations Ken and Helen, who force him to confront some painful truths about his life. Just before arriving at the university, Richard dies peacefully in the car.
Distressed, Harry literally slides out of focus, becoming blurred like one of his own fictional characters. Cookie helps him restore focus. The university's staffers gush over Harry, asking what he plans to write next. He describes a story about a man (based on himself) who journeys down to Hell to reclaim his true love (based on Fay) from the Devil (based on Larry - both being played by Billy Crystal). Harry and the Devil engage in a verbal duel as to who is truly the more evil of the two. Harry gets as far as arguing that he is a kidnapper before the story is interrupted by the arrival of the police. Harry is arrested for kidnapping Hilliard, for possessing a gun (it was Lucy's), and for having drugs in the car (belonging to Cookie).
Larry and Fay come from their wedding to bail Harry out of jail. Harry reluctantly gives them his blessings. Back at his apartment, a miserable Harry fantasizes that the university's ceremony is taking place. Harry realizes that he can only function in art, not in life. The film ends with Harry returning to his writing.
Deconstructing Harry garnered 71% approval on Rotten Tomatoes and a 61 out of 100 on Metacritic.
Woody Allen was nominated for an Academy Award for Best Writing, Screenplay Written Directly for the Screen for Deconstructing Harry. The film was also nominated for a Golden Satellite Award for Best Motion Picture — Comedy or Musical.
The film is a general reworking of his earlier 1980 film Stardust Memories, which also had an artist go to a ceremony in his honor, while reminiscing over past relationships and trying to fix and stabilize current ones.
Allen is an admirer of several European directors whose primary body of work was completed sometimes decades before his first script, and his films in particular often draw upon the works of Ingmar Bergman and Federico Fellini. The rough outline of the plot of Deconstructing Harry, that of an academic on a long drive to receive an honorary award from his old university while reflecting upon his life's experiences, essentially mirrors that of Bergman's Wild Strawberries. Also, the film is similar to Fellini's 8½, in that it is about an artist struggling with his current relationships and remembering his old ones, interspersed with dream sequences, as well as his work being based on events from his life.
It is acknowledged by some critics that Allen based the name of Harry Block on Antonius Block (Max von Sydow), the protagonist from Bergman's The Seventh Seal. Some critics, including Roger Ebert, have suggested that the character of Harry Block is based on real-life author Philip Roth and not on Allen himself.