19. Sleepless in Seattle (1993)
Director: Nora Ephron
Areas Featured: Empire State Building
As a nod to An Affair to Remember, a would-be couple agrees to meet on the observation deck of the Empire State Building on Valentine's Day. Which is crazy romantic, except for the fact that they've never met before. Sam's son basically hooked them up, and he was, like, nine.
It may sound more creepy than sentimental, but ignore our cynicism. Thanks in part to the film being backed by America's sweethearts, Tom Hanks and Meg Ryan, the fateful meeting atop one of NYC's greatest landmarks has become one of the most recognizable scenes in movie history, cementing the skyscraper's status as one of the most enchanted places in Manhattan.-TA