Final Fantasy 8. I popped that disk into my PS1 and was blown away by how amazing the movie looked. Obviously it doesn't hold up anymore, but the whole first time experience is now a core memory.

Driver by The Future Kings of Nowhere. It's a folky song about some guy telling the taxi to drive to California to see his love. Talks about how well he knows her, how he kissed her goodnight, and how they are going to build a life together. Then, we find out he has never introduced himself to the girl.....

Edit: 10 simple murders by the same band is a good one too. Pretty self explanatory.