Woody Allen goes to hell.
Yet there is something quite touching about the way that Allen communicates that Harry still regards his sister as a "wonderful kid" who has been as devoted to Harry as to her religious convictions. Allen definitely does not condemn Doris's religious observance here, unlike his character, Harry. In fact, his critique of excessive observance for its own sake in the short story is rendered all the more authentic and effective by the tenderness he shows for Doris in clear criticism of Harry.
Although clever, the other short story sequences, particularly a nasty "exposé" of Harry's parents, lack this knowing quality. The only other sequence that carries moral weight as a short story is an impressive allegory about an actor, nicely played by Robin Williams, who discovers that he is intrinsically "out of focus." As for the acting, Kirstie Ally is most effective as the mother of Harry's son. Most of the other stars in the film, especially Billy Crystal, are used as exaggerations of persona for which they are well known, and which are already overdone, whether in Allen's previous work or in their own.
The Elevator to Hell
By the end of the film, Allen convinces himself, and tries to snow us into believing, that the movie is about knowing one's limitations, and getting on with one's life. True, Deconstructing Harry demonstrates, in many ways, the most self-awareness of any of Allen's films. But it is not a meditation on self-awareness. It is, rather, a deliberate choice and action on Allen's part.
In one segment, half story and half daydream, Harry takes an elevator into Hell (the commentary in the elevator is delicious), and meets his father in Gehenna [a term used for the traditional Jewish equivalent of Hell]. Not surprisingly (for easy laughs in an Allen film), Dad is wearing a yarmulke. He has been consigned to Hell for being too critical of Harry (of course).
For a precious moment it seems that Harry will find closure and renewal and even achieve a kind of teshuvah (repentance). Instead, like an annoying old habit impeding and even discouraging growth and maturity and decency and awareness of responsibility, the Hell scene degenerates into Dad qua "religious" Jew rejecting the Heaven option (speaking for Allen?): "I am a Jew. We don't believe in Heaven." When Harry asks his Dad where he wants to go, the yarmulke-wearer says, "To a Chinese restaurant." (Allen and the writers of the contemporaneous television series, The Nanny, seem to relish the same, tired, American Jewish jokes.)
In one fell swoop, then, Jewish beliefs in Heaven and in the sanctifying power of dietary disciplines are traded away--and for what? For the "ultimate one-liner" that follows--an off-color joke about Hadassah women. Again, a cheap Woody Allen remark about Jewish women and their largest and most accomplished philanthropic organization. In this movie, that crack is the definitive statement on Heaven and Hell--unlike the earlier pictures, where such references were little more than asides and stage whispers.
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