(1997) Lucy (Judy Davis) repeatedly gets out of a taxi at the opening of this comedy by director/writer Woody Allen of a writer too neurotic to function in life, only through his fiction, to ring the bell at Harry Block's door, interrupted by credits, to deliver her tirade of disgust and revulsion against the writer (Allen) for using incidents from her life (such as her giving him a blow job at her father's funeral), their relationship (an affair while he was married to her sister), for his book: "suffering turned into literary gold."
In the book Lucy is barely veiled as Leslie (Julia Louis-Dreyfus) and himself thinly disguised as Ken (Richard Benjamin). In another story he wrote of his first marriage with himself as Harvey Stern (Tobey Maguire), a shoe salesman, married too young, horny for every woman he meets except his wife; taking the recommendation of his boss to hire a prostitute (being with a harlot isn't cheating), Harvey appropriates the bachelor pad of his pal Mandel Birnbaum, who's in the hospital after an automobile accident, but just as he's about to go another round with the whore, death comes to the door, mistaking Harvey for Mandel. The tale saves Harry's life because Lucy, holding a gun on him, finds it funny.
Collecting aphorisms ("Women are God," Harry tells his ten-year-old son Hilly at school, as they discuss names for penises, which a mother overhears), casting aspersions (his half sister Doris decries his being "a self-hating Jew"), and flinging filthy language everywhere, characters multiply like words on a page: Mel (Robin Williams), an actor who's literally out of focus (Harry's shrink explains: "You expected the world to adjust to the distortion you've become"); Paul Epstein (Stanley Tucci), who falls in love with his female psychiatrist Helen (Demi Moore); Goldberg, whose lover gets abducted by the devil; Dolly (Shifra Lerer), who learns of the dark secret her husband of 30 years, Max (Hy Anzell), has been keeping from her - his having previously been married in Florida with two children along with an affair with another woman, all of whom he murdered with an ax and then cannibalistically consumed (a fictionalization of his parents).
Harry tries to rationalize with his first wife Joan (Kristie Alley), a psychiatrist, who denounces his having broken a "sacred trust," his having fornicated with her patient as nothing more than a meaningless, passionate affair (as a means of getting closer to her after she'd turned away from him following the birth of Hilly), which can't compare to their having a solid, stable marriage.
Having been invited to receive an honorary award and ceremony from Adair University, his alma mater, upstate from New York City, but suffering from writer's block for the first time in his life, Harry asks various friends and former lovers to accompany him. Ex-flame Fay Sexton (Elisabeth Shue) turns him down because she's getting married the next day to his old friend Larry (Billy Crystal), who has put his art into living well. Later Harry will imagine going to hell on an elevator (opportunity to settle old scores) where he finds his father (Jews don't believe in heaven as paradise, only in Chinese restaurants) and Larry (a fallen angel in charge with air-conditioned digs) who has kidnapped Fay.
Eventually he gets Cookie (Hazelle Goodman), a black daughter of joy - "Do you know what a black hole is?" asks Harry, the "spiritually bankrupt" atheist who only believes in physics; of course, she replies, "That's how I make my living" - Richard (Bob Balaban), whom he'd accompanied to the hospital the day before for a false alarm of a heart attack; and his son against Joan's wishes. On the way Harry encounters his book's characters, Ken at a carnival and Helen at a gas station. He arrives at the college with a hooker and a dead body.
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