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konastab01
Do you mean depressing or bittersweet, break-up-esque tunes we love to get sad on?
If the latter:
Mazzy Star - Fade Into You http://www.youtube.com/watch?v=XucegAHZojc
Cat Power - Hate http://www.youtube.com/watch?v=rsfdW8xAZRY
Fleetwood Mac - Landslide (and most other songs about getting older) http://www.youtube.com/watch?v=WM7-PYtXtJM&ob=av2n