That's really what i was thinking of. Awesome. Thanks for all the quick responses!
Setting: totally irrelevent. Its modern day Baltimore, U.S. but the song can be from any group artist or band, from any country, as long as its in English.
Basically, what I need is a song that is about someone who goes from the high life to barely alive, dead, homeless on the streets, or totally ruined from drugs and alcohol. A kind of warning about fame and celebrity and that sort of thing.
This is a character who knows a lot about music, who likes eclectic music, and just about anything could plausibly be on her ipod. So obscure is okay. any era is okay, although 1950's-modern day would be preferable.
Although I'm pretty sure there is a non obscure answer. I just can't think of anything, and i'm wading through various combinations on google, and also my own personal song collection, but no luck so far. So if anyone can think of anything, that would be amazing.