Deconstructing Harry (1997)

Plot: 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 Lucy's 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 Harry's friends, Larry. The day before the honoring ceremony in the midst of a writer's 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 Hilly's 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.