The staying power of this film hinges on the two main characters, Sam (played by Tom Hanks) and Annie (played by ubercutie Meg Ryan). Sam is a widower with a young son, still in pain a year and a half after his wife's death. Annie is engaged to a man she likes very much, but doesn't love. Hanks and Ryan are so delightfully likeable, and so well matched that one is easily engaged in their story.
An especially interesting thing about "Sleepless" is that it uses a plot ingredient from "An Affair to Remember" (with Cary Grant and Deborah Kerr, a bonafide classic on its own). The climax of the film is directly related to "An Affair to Remember"-with different results, of course.
This film is powered by magic. The kind that doesn't require a light sabre or a ring inscribed with elvish words. The kind of magic that appears in the real world---and in this case, Seattle, Baltimore, and New York City. And at the most magical times of the year (according to the card companies!): Christmas Eve and Valentine's day. It isn't even about two people in a relationship. It's about two single people who need a relationship and that "special magic". This film gives you hope. Hey, if Sam and Annie get it right, why can't we?
And in the end, the film is not so much about romance, but about trusting yourself. Annie trusts herself to pursue Sam, and Sam trusts his ability to love again. It's about second chances. Oh alright, it's about romance too. I'll look the other way when you rent it.
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