I just saw (500) Days of Summer again, and it was even better the second time. I love love love love it, and Zooey Deschanel, and everyone else is just awesome. And, I won’t spoil it I hope to say that in one scene people dance to this song and it’s simply the best thing ever in the whole world. It’s exactly what musicals assume — that people just start singing and dancing in their everyday life — except it really conveys that feeling in a way that no other narrative technique really could.
It’s actually a pretty out-there movie, narrative-wise, at least as much so as, say, Memento. The trick with fooling with structure in that way is to only do it when it really 100% fits the story; in Memento, for example, the structure is as it is because it reflects the protagonist’s understanding of the world and mindset. Similarly with this, since it’s so tight on Tom’s POV. And, relationships live on after they end in memories, and those memories aren’t linear but skip around: one great moment to the next, or one sucky moment to the next.