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 "Who are you?"

"It's me, Ken!"

"... Ken?"

"Look at this guy! You created me, now you doesn't recognize me?"

Successful author Harry Block has been routinely mining his real life for material. After his latest divorce, he's been dating a young fan of his work - who just left him. Now he has to deal with an upcoming trip to his alma mater, and some of his characters start checking up on him in real life. A pretty poignant case of Family-Unfriendly Aesop follows.

Tropes used in Deconstructing Harry include:

  "To Evil! It keeps things hummin'."

  • Author Avatar: To some degreee, each and every main character from Harry's stories resembles him.
  • Brick Joke: One of Harry's (perhaps unfinished) short stories deals with an actor (Mel) going out of focus as he's shooting what appears to be a TV commercial. Later on, the same thing happens to Harry, in lieu of a panic attack.
  • The Cameo: Robin Williams as the out-of-focus actor, Tobey Maguire as a young Author Avatar,
  • Canon Sue: In-universe: "Ken", the main character in Harry's last novel, comes off as a charming, laidback guy, all too happy to explain what went wrong in Harry's life. He's right every time.

 Harry: "How do you know so much?"

Ken: "Well... I'm just you. Thinly disguised. You gave me a little more maturity. And a different name."

  • Critical Psychoanalysis Failure: Joan might have needed a lot of help after being cheated on with one of her patients and getting divorced; we know she didn't take it well.
  • Death by Childbirth: Happened to Harry's mom; his father never quite forgave him for that.
  • Family-Unfriendly Aesop: Whatever it is.
  • Functional Addict: Harry sees himself as one, as far as booze and anti-anxiety pills are concerned. Other characters don't agree.
  • The Fundamentalist: Played with, twice:
    • In one of Harry's stories, this is the reason his marriage to his former psychoanalyst failed: after the birth of their son, she rediscovered her Jewish roots, became obsessed with faith and tradition, and ended up leaving Harry for a dashing Israeli patient. In real life, though, Harry cheated on Joan with one of her patients.
    • Then there's Bert, Harry's brother-in-law; an observant Jew who Harry despises to the point of becoming estranged from his sister. They later briefly reconnect.
  • Hey, It's That Guy!: Paul Giamatti pops up near the end as a Lit professor; there's also a 5-second glimpse into Sydney Bristow before she became an agent.
  • High Class Call Girl: The Asian prostitute in one of the stories-within-a-story.
  • Hollywood Atheist: Mostly played for laughs, of the smug variety.
  • Hooker with a Heart of Gold: Cookie.
  • Ironic Hell
  • The Lancer: Larry.
  • Laser-Guided Karma: Borrow a sick friend's apartment, pretend it's your bachelor pad, use his name to introduce yourself to a High Class Call Girl... hey, that's The Grim Reaper at the door. And he won't believe you're not the guy.
  • May-December Romance: Applied twice. Fay, Harry's last girlfriend, left him for Larry, who's older than her as well: the key difference here is Larry's positive outlook on life. They're married by the end of the movie.
  • Meaningful Name: Harry Block, although Writer's Block is just a symptom of his depression.
  • Morality Pet: Played with. Harry's very fond of his young son Hilliard, who he enjoys spending time with; too bad all his life lessons to the kid are variations on Good Is Boring.
  • Muse Abuse:
  • Pygmalion Plot: Seems to have played a major role in Harry and Fay's romantic relationship; he considered her "a fan, then a pupil", but in the end he fell in love and she didn't truly reciprocate his feelings.
  • Show Within a Show: Harry's stories within the film - and then The Reveal that the entire movie is the new story by Harry about himself.
  • The Shrink: Joan and her fictional counterpart.
  • Sidekick: Harry's friend and colleague Richard.
  • Unproblematic Prostitution: Played with: Cookie comes off as a self-assured, reasonably content sex worker, who acceps Harry's offer of money in exchange for accompanying him to his old college even if she met him a couple hours before (and therefore has no idea whether he could posit a danger to her). She's also treated far more nicely than any other female character in-universe.

  Harry: "Every hooker I ever speak to tells me that it beats the hell out of waitressing. Waitressing's gotta be the worst fucking job in the world."

  • Villainous BSOD: Once the group arrive at Harry's alma mater, they find out his friend Richard - who they thought was simply dozing off - has died in his sleep, presumably of a heart attack; Harry panics and briefly goes out of focus.
  • What the Hell, Hero?: Happens at least twice, with characters from Harry's stories ("Ken" and "Helen", the latter being a mix between his ex-wife and his sister) lecturing him on the mistakes he made in his personal life.
  • Write Who You Know: With almost no exception, Harry's characters are thinly-veiled versions of people he knows; considering in real life he's a bit of a Magnificent Bastard, every time he's got a new novel out, at least one of his personal relationships goes very sour.

  "And of course there's Jane, or, as you pathetically disguised her... Janet."

    • Even he occasionally can't tell the difference between real life and fiction.

 Lucy: "Oh big fucking deal, you gave her large breasts!"

Harry: "Leslie, please..."

Lucy: "Lucy. I'm Lucy, motherfucker. Not Leslie."

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