Last winter, I was on the bus leaving campus and there was this really greasy hairy prick from my English Lit class running down the path trying to catch the idling bus before it left. On my iPod I was listening to Imogen Heap - Hide and Seek and just as reached the infamous "MMMM Watchya Say" Part, the dude slipped on some ice and fell down, allowing the bus to pull away as he longingly reached his hand out as if grasping for it - as it turned around the U-shaped driveway to leave campus.
The timing, the music, the expression on his face. It was the perfect coincidence, I couldn't stop laughing until I was like halfway to the station.
That's the greatest story I have of soundtracking real life. Though I wish I could have someone following me with a boombox playing the shaft theme song every time I entered some place new; I'd make a boss first impression, every time.