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Woody Allen’s Deconstructing Harry

Deconstructing Harry deals with themes such as fear of commitment and the complexity and difficulty of long term, intimate relationships.  Woody Allen plays protagonist Harry Block (as his name would suggest, he suffers writer’s block).  The film is a hilarious and twisted tale filled with infidelity and betrayal, all the while a writer tries to follow his heart.  What Harry leaves in his wake is the consequence of his artistic expression and his fidelity to his authentic self. 

Psychological and Philosophical Grounding 

The name of the film, Deconstructing Harry, hints at its psychological focus. Harry’s first wife Joan (Kirstie Alley) is a psychologist.  Furthermore, the film itself is a journey into the psyche of its protagonist Harry Block, who is unapologetic for his transgressions and infidelities. 

Yet “deconstructing” could also refer to literary analysis, in this case germane given the protagonist’s profession, a writer and novelist.  Indeed, the film features many literary allusions (Godot, Kafka, Sophocles, etc.).  Allen’s work often feels literary, which might have limited his audience, but greatly enriches his work.

In fact, the film itself is like a confusing but rewarding novel.  This is in part because the film follows the plots of Harry’s short stories and novels, which mirror his own life. Some characters are composites of different people in his life.  Harry’s fiction represents his various marriages. Meanwhile, his wives are represented by actresses portraying both his real-life wives and the wives represented in his fiction. As you can see, this makes following the plot a little fraught. 

The film’s various disjointed jump-cuts symbolize the fragmentation that Harry feels in his life. The film is indeed fragmented, jumping from depictions of Harry’s fiction back into his life with little transition.  

Philosophically, Deconstructing Harry portrays an existential outlook towards life which Allen himself shares (Schickel 10).  Furthermore, there are explicit references to a loss of faith–or maybe a lack of faith is a better way to phrase it if one never had religion.   

As a writer, Harry’s protagonists are thinly veiled versions of himself.  This is what so infuriates the people around him.  They find themselves portrayed in his novels and don’t appreciate it, especially to the extent that it makes them relive their unpleasant relationship’s with Harry.  Meanwhile, he hardly understands the pain he causes to other people, particularly women. 

Story Within a Story 

One of Harry’s autobiographical stories features  protagonist Harvey Stern, played by Tobey Maguire.  Maguire is just one of the many delightful cameos in Deconstructing Harry.  Anyway, Stern is hopelessly bored with his wife, yet very attracted to just about any other woman: 

“I don’t know what it is, I’m just not attracted to her [...] I’m hyper-sexually aroused, just not for her [...] The truth is I never meet or see a woman that I don’t wonder what it might be like to wind up in bed with her.” 

This story reflects the sense of restlessness and even sexual addiction with which Harry is afflicted.  He fantasizes about every women he sees, so he can hardly expect to have some type of tranquil domestic situation.  Yet he’s been married three times, so it isn’t for lack of trying.

Harry has a fraught relationship with his nine-year-old son Hilly, to say the least.  It’s not necessarily because there’s resentment between him and his son; but rather, because his ex-wife seeks to block (no pun intended) his contact with his son.  He’s accused of inappropriate conversation with his son.  Yet this was just a case of oversharing that was misinterpreted by his wife’s busy-body friend Beth Kramer (played by Mariel Hemingway), for whom Block has some choice words.  

There are several flashback sequences as Harry is on the way to receive an honorary degree (or receive some unspecified honor) from his old school.  Through a variety of circumstances, he finds himself accompanied by a black prostitute, his friend Richard, and his son Hilly.  Harry had hired the black prostitute, Cookie, the day before the trip, and then realized she might be good company, thinking he had no other.  Block conducts himself ironically with Cookie, making literary allusions she couldn’t possibly understand.  Yet in her openness and earnest desire to understand Block’s problems, she’s a welcome companion at least for their ephemeral interaction. “What’s so special about this honor anyway?” she asks ingenuously on the ride to the event. 

Along the way, Richard dies in the car due to a heart condition.  Cookie says to no one in particular, “He’s dead, honey.  You got one of those rubber bags?”  Cookie, whose presence initially seemed like a farce, turns out to be a source of strength and moral support for Harry. 

On a stop along the way to the event, Harry has a surreal conversation with one of his characters.  His protagonist Ken (again a version Harry) explains to him regarding his ex-wife Jane: 

“That’s why you picked her.  So it wouldn’t work.”  

It’s an insight into Harry’s fear of commitment, and the subtle ways in which he sabotages his relationships so that he could ultimately have what he wants: sexual freedom and more options.  When Harry pushes back on this, Kent tells him: 

“Hey, you can’t fool me.  I’m not your shrink.  He only knows what you tell him.”  

This brings to light a kind of circular problem with therapy, which is that the therapist’s only reference point into your life is your version of events.  In that sense, one biases one’s own therapist and the objective facts remain elusive. 

In a scene in which Harry pictures himself in hell, with Billy Crystal cast as the devil, Harry catalogs his character defects: 

“I do terrible things.  I’ve cheated on all of my wives, none of them deserved it.  I sleep with whores.  I drink too much.  I take pills, and I lie. I’m vain and cowardly…” 
Billy Crystal appears as the devil

Indeed, Harry has a bad romantic track record.  He even admits to one of his girlfriends, “I can’t love.”  Well, she was warned.  Harry characterizes marriage in terms of being “routine” and plodding along with a lack of passion, whereas his affairs he characterizes as being passionate.  Quite reasonably, he wonders if marriage is for him. 

His ex wife, (played by Kirstie Alley) interrupts the proceeding in which Harry is to be honored to accuse him of kidnapping his own son, such is their acrimonious relationship.  As Harry had explained to his therapist, it wasn’t his visiting time.  Plus, their marriage ended disastrously: Harry had an affair with one of her therapy patients, so it is no surprise that they don’t have a good relationship post-marriage.    

The police arrive to make an arrest.  Harry tries to bargain with them with a touch of narcissism and humor: 

“Can’t I be honored and then arrested?”  

In the end, however, Harry learns what if feels like to be betrayed.  Is this poetic justice, or was there something he did to deserve it?  On second thought, those are the same thing. When his old friend Larry and his former lover ask for his blessing in getting married, Harry concedes: “I give up,” and gives them a hug.  It feels like letting go, and seems therapeutic in itself.


The film gives a fairly unadulterated view of the male perspective through Harry Block.  It may not be the only male perspective, but it is undeniably one.  The New York Times called it misogyny (though they gave the film a positive review).  To be fair, the NY Times reviewer was female, so perhaps she’s not the expert on the male perspective.  The fact is, Harry finds women in his life to be fairly expendable and he can hardly apologize when he needs to move on (or cheat) in order to fulfill his sexual pleasure.  It isn’t morally right, but it is shockingly honest.   

Art Imitating Life? 

Harry Block appears an exaggerated version of Woody Allen himself, especially considering Harry’s  profession and his girl problems.  Allen always plays a “single, highly defined character” (Schickel 6) which is at least presumed by audiences to be similar to Allen himself.  As film critic Richard Schickel put it, “There are disguised aspects of his personal history in many of his films” (34). 

Schickel views Deconstructing Harry as Allen thumbing his nose at a public which was in the midst of the scandal concerning Mia Farrow and the (in my view false) child abuse allegations. In this view, Allen was “flinging this figure [Harry] in the face of his bad publicity” (56), and in some way expressing Allen’s rage. This would explain the sharper tone to Deconstructing Harry as compared to Allen’s other work.

Indeed, just as Woody Allen was not overly concerned about the public’s perception of his relationship with Mia Farrow’s adopted daughter, Harry Block is not too worried about carrying on an affair with his wife’s sister.  As the NY Times put it in their review of the film: 

“... the person ruled by creative imagination may be indifferent, not to say ruinous, to the happiness of those around him.”

Indeed, Harry is rather nonplussed by how devastated this leaves both sisters in his wake. 

Grade: A

Works Cited

Deconstructing Harry. Directed by Woody Allen. Performances by Woody Allen, Tobey Maguire, and Billy Crystal. Sweetland Films, 1997.

Schickel, Richard. Woody Allen: A Life in Film. Chicago: Ivan R. Dee, 2003.

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