I always liked Fleetwood Mac's Gypsy - with Stevie Nicks' angelic voice - and I found out recently that the song has a very sad meaning: Stevie's mentor, confidante and friend Robin Anderson found she was pregnant during the recording of the song, then she discovered she was dying and passed away shortly after the birth of her son Matthew. :bluesad:
https://www.youtube.com/watch?v=mwgg1Pu6cNg (https://www.youtube.com/watch?v=mwgg1Pu6cNg)
I always liked the Prince song "7" but the lyrics are cryptic. This is the only song Prince was tight-lipped about, never telling anyone what it is really about. I like that it remains an "unsolved" mystery.
My Sharona by The Knack and Brown Suger by The Rolling Stones.