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Harry Block is a well-regarded novelist whose tendency to thinly-veil his own experiences in his work, as well as his un-apologetic attitude and his proclivity for pills and whores, has left him with three ex-wives that hate him. As he is about to be honored for his writing by the college that expelled him, he faces writers block and the impending marriage of his latest flame to a writer friend. As scenes from his stories and novels pass and interact with him, Harry faces the people whose lives he has affected - wives, lovers, his son, his sister.
Harry Block, an atheist who grew up in a Jewish home, is a successful New York based writer of novels and short stories. That success has resulted in him being honored imminently in a special ceremony upstate at Adair University, from where he was expelled when he was a student. However his personal life is a mess, as viewed by his stories, all which have some element of autobiography, either directly or as an allegory to issues in his life. Thus, most of the people about who he writes hate him because he exposes what should be their private lives to public scrutiny. Those people include three ex-wives and counting, Lucy, a former married sister-in-law with who he was cheating when he was married to Lucys sister Jane, but who he left for a younger woman, and his estranged half-sister Doris, who re-embraced her Jewish faith when she married her current husband, Burt. Lee, that younger woman who he claims is the true love of his life, recently left him for one of Harrys friends, Larry. The day before the honoring ceremony in the midst of a writers block, Harry, in therapy, realizes that his love life is as screwed up as when he was a young man, he always doing something to sabotage relationships, while preferring the company of whores if only to place sex in a business context. He wants someone to go with him to the ceremony, most specifically his adolescent son Hilliard, which Hillys mother, Joan, who is still bitter toward Harry, will not allow. As he drives upstate to Adair, Harry picks up a few people and makes a few stops along the way. Who also follow him are a few of his stories characters, who, if Harry will listen to them, may give him a better insight into his dysfunctional life.
Woody Allen
Harry Block
Judy Davis
Lucy
Julia Louis-Dreyfus
Leslie
Stephanie Roth Haberle
Janet
Dan Frazer
Janet's Dad
Joel Leffert
Norman
Lynn Cohen
Janet's Mom
Richard Benjamin
Ken
Joe Buck
Yankee Announcer
Jane Hoffman
Grandma
Tobey Maguire
Harvey Stern
Annette Arnold
Rosalee
Frederick Rolf
Harvey's Doctor
Elisabeth Kieselstein-Cord
Rosalee's Sister
Lortensia Hayes
Jennifer
Alicia Meer
Woman in Shoestore
Victoria Hale
Woman in Shoestore
Irving Metzman
Shoe Salesman
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