How Well Do You Know ‘Sleepless in Seattle,’ ‘When Harry Met Sally…’ and ‘You’ve Got Mail’?

Photo courtesy of the AF archive and Alamy Stock Photo

Nora Ephron’s direction of Sleepless in Seattle, which spikes its sentimentality with her trademark wry, observant humor, is a wonderful, fundamentally hopeful film that contains many lovely elements, including Tom Hanks at his most Tom Hanks-iest; Meg Ryan at the height of her rom-com powers; a soundtrack full of sweet standards; a baby Gaby Hoffmann using social-media to express herself; and a soundtrack filled with sweet standards. Sleepless in Seattle is fantastic, and if you attempt to tell me it isn’t as wonderful as You’ve Got Mail, please keep your mouth shut because you are completely incorrect.

The film’s 25th anniversary — Sleepless premiered in cinemas on June 25, 1993, and quickly rose to become one of the year’s highest-grossing pictures — it seems only appropriate to recognize the film’s most worrisome component, as well as the character who is most severely impacted by it. Walter, a guy who gets ditched in the middle of a Valentine’s Day meal so his fiancée (Ryan) may go off and test her chemistry with some male she doesn’t know (Hanks) on the top of the Empire State Building, is the protagonist of the film. And, for some reason, Walter seems completely unconcerned about all of this.

Sleepless in Seattle establishes fairly quickly that Annie, a normally practical woman, is capable of falling in love with Tom Hanks based solely on the sound of his voice — millennials who had a crush on Woody in Toy Story, I’m sure you can relate — and that she has been brainwashed by a lifetime of watching classic romantic films, to the point that she believes anything less than an epic cinematic romance is possible. Sleepless in Seattle is directed by David O. Russell

Despite the fact that the film explicitly implies that such behavior is delusional — “You don’t want to be in love,” for example — “You want to be in love in a movie,” Annie’s closest friend Becky (Rosie O’Donnell) correctly observes — and Sleepless in Seattle demonstrates that Annie is correct in the end. If you have a little tenacity, a dash of stalking, an obsession with An Affair to Remember that is severe enough to qualify as a mental illness, and the assistance of a stubborn kid who runs away from home solely to confirm that Annie from Baltimore is, in fact, his widower father’s destiny, it is possible to find the kind of connection that only appears to exist on TCM.

Oh, and there’s no pressure to completely screw up Walter, the fiancé played by Bill Pullman, who is presented as the physical epitome of being cautious and cautious. Walter may be the ultimate example of the pleasant, somewhat boring person who is discarded in favor of someone who is more suited to igniting the passions of a female heroine. See, for example, Lorenzo Lamas in Grease, Danny Aiello in Moonstruck, Paul Rudd in Baz Luhrmann’s Romeo + Juliet, and James Marsden in The Notebook for further examples of this cliché. as well as Superman Returns… and, of course, Enchanted.


“Start the Quiz”

  • Question of

    Where does Annie ask Sam to meet her in ‘Sleepless in Seattle’?

    • In Central Park
    • At the top of the Space Needle
    • At the top of the Empire State Building
    • At Pike Place Market
  • Question of

    Who played Harry in ‘When Harry Met Sally’?

    • Tom Hanks
    • John Cusack
    • Billy Crystal
    • Harrison Ford
  • Question of

    What’s the name of Tom Hanks’s character in ‘Sleepless in Seattle’?

    • Sam
    • James
    • Sonny
    • Brad
  • Question of

    Where does ‘You’ve Got Mail’ take place?

    • Boston
    • New York City
    • Chicago
    • San Francisco
  • Question of

    Which of the following actresses starred in ‘When Harry Met Sally,’ Sleepless in Seattle’ and ‘You’ve Got Mail’?

    • Julia Roberts
    • Sandra Bullock
    • Meg Ryan
    • Kate Hudson
  • Question of

    Which actress plays Suzy, Sam’s sister, in ‘Sleepless in Seattle’?

    • Rosie O’Donnell
    • Parker Posey
    • Carey Lowell
    • Rita Wilson
  • Question of

    Who says the following line from ‘You’ve Got Mail’? ‘It’s a lovely store, and in a week it will be something really depressing, like a Baby Gap.’

    • Jessica
    • Kathleen
    • Becky
    • Joe
  • Question of

    During the car trip to New York in ‘When Harry Met Sally,’ what does Harry say he believes men and women can never do?

    • Be friends with each other
    • Be honest with each other
    • Have meaningful relationships with each other
    • Be faithful to one another
  • Question of

    Can you tell us what Kathleen’s screen name was in ‘You’ve Got Mail’?

    • WestSidegirl
    • SAdgirl
    • Shopgirl
    • Bookgirl
  • Question of

    Which ‘When Harry Met Sally’ character said, ‘When I buy a new book, I read the last page first. That way, in case I die before I finish, I know how it ends.’

    • Harry
    • Jess
    • Marie
    • Sally
  • Question of

    Which actress played Sally’s best friend Marie in ‘When Harry Met Sally’?

    • Gilda Radner
    • Patricia Arquette
    • Debra Winger
    • Carrie Fisher
  • Question of

    ‘When Harry Met Sally’ was written by Nora Ephron. Who directed the film?

    • Richard Curtis
    • Rob Reiner
    • Gary Marshall
    • Albert Brooks
  • Question of

    Do you remember the name of the bookstore chain Joe runs in ‘You’ve Got Mail’?

    • Barnes & Noble
    • Fox Books
    • Joe’s Books
    • Borders
  • Question of

    Can you finish this quote from ‘Sleepless in Seattle? ‘Destiny is something that we’ve invented because we can’t stand that fact that everything that happens is __________.’

    • ‘Bad’
    • ‘Accidental’
    • ‘Painful’
    • ‘False’

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