YMMV / Sleepless in Seattle

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• Alternate Character Interpretation: Are Jonah's shenanigans the attempt of a grieving son to prevent his mother's "replacement" (as his father believes) or sincerely motivated by an affinity with Annie? Basic logic favors the former interpretation, but Jonah is proven completely right by the end of the movie, and goes to incredible lengths to make Annie/Sam happen. One could also argue he doesn't want to have his father settle for just any replacement but rather a woman who is right for him - after all, he reads Annie's letter and gets a good vibe from her.
• Awesome Music: The entire Soundtrack. Filled with nostalgic favorites like "Make Someone Happy", "As Time Goes By", "Stand By Your Man", "Stardust", and "Makin' Whoopee" to Oscar Nominated "A Wink and a Smile" by Harry Connick Jr. and the stunning cover of "When I Fall In Love" by Céline Dion and Clive Griffon, it's one of the most memorable parts of the movie.
• Designated Villain: Victoria. Her laugh is annoying as hell, yes, but other than that, she seems like a perfectly nice person.
• Funny Moments: Jonah matter-of-factly asking Sam, "If you get a new wife, I guess you'll have sex with her, huh?" and Sam's Spit Take (they're brushing their teeth).
• Hilarious in Hindsight: David Hyde Pierce appears in this film prior to his debut as Niles on the Seattle-set series Frasier (and yes, a title card from the first season would reference this film). Even better, Tom McGowan (Keith) would later join Frasier’s cast as KACL station manager Kenny Daly.
• Memetic Mutation: The movie was released in 1993, yet "______less in ___________" is still recognizable as a pun on its title.
• Memetic Psychopath: Due to the stalking and wanting to leave her fiance to pursue a man she barely knows, Annie gets this a lot from viewers.
• Older Than They Think/Shout-Out: One particular line from the Meg Ryan character:
  Annie Reed: This man sells the greatest soup you have ever eaten, and he is the meanest man in America. I feel very strongly about this, Becky; it's not just about the soup.
  • Who was she referring to? It was Ali Yeganeh, the Real Life version of Seinfeld's "Soup Nazi", two years before they did the famous episode on him! (And, before this Yeganeh's restaurant had been the subject of a 1989 article on The New Yorker.)
• Retroactive Recognition:
  • Jonah is the original voice of T.J. Detweiler.
  • One of Annie's relatives is played by Frances Conroy, who'd become better known for Six Feet Under and American Horror Story.
• Ron the Death Eater: Annie is often imagined as a spiteful, ungrateful harpy who breaks Walter's heart and "dumps" him for a guy she's never met. In fact, Annie goes on about how crazy her feelings for the idea of Sam are, and she's called on her unrealistic expectations by other characters. Her and Walter's breakup is actually a mutual one, where Annie herself is the one who was keen to marry him anyway, and he realised it wasn't going to work.
• Special Effect Failure: The closing shot is a digital image of the New York City skyline which did not stand the test of time.
• Tear Jerker: Dear GOD, and how:
  • The beginning of the movie which shows Sam and Jonah standing at Maggie's grave. The fact that the film immediately starts with this lets us know what kind of a movie we're in for.
  • Annie crying while listening to the radio with Sam talking about his late wife.
  • Jonah and Sam reminiscing about Maggie, after Jonah wakes up to a nightmare. Especially this line from Jonah:
    Jonah: I'm starting to forget her.
  • Jonah and Sam's argument the night before the former runs away to New York to find Annie.
  • Annie and Walter's breakup, for how amicable it is. Walter graciously says "I don't want to be someone that anyone settles for". There's no fight, there's no crying, just honesty about how they aren't in love enough to be married.
  • The emotional climax with Sam and Jonah reuniting at the Empire State Building.
  • The ending with Annie finally meeting Sam and Jonah brings on more happy tears.
• Unintentional Period Piece: The Twin Towers are visible in shots of the Manhattan skyline, clearly placing this movie pre-9/11. Jonah interrupts Sam’s date by calling him on the restaurant’s phone when nowadays he'd use a cell phone.
• The Woobie:
  • Sam becomes this within the film after he talks about his wife's death on the radio show - Annie is not the only woman woobifying him.
  • If one thinks about it enough, Walter, Annie's original fiance is the biggest Woobie of this film. He's basically shown to have hilariously awful allergies and health issues, and at the movie's end, is told that his fiancée essentially wants to leave him for a man she's never met met once and exchanged two words with (both words being "hello"). He accepts this with amazing grace, but geez...

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