My list of depressing songs: some of these are quite old and obscure, but if your blue funk isn't blue or funky enough, these'll get you there:
Alone Again (Naturally) - Gilbert O'Sullivan
Toby - The Chi-Lites
The Beginning Of My End - The Unifics
The Coldest Days Of My Life - The Chi-Lites
Honey - Bobby Goldsboro
Last Kiss - J. Frank Wilson And The Cavaliers (later by Pearl Jam)
Sitting On The Dock Of The Bay - Otis Redding
Starry Starry Night - Don McLean
Brandy - The O'Jays (NOT Brandy (You're A Fine Girl) by Looking Glass, although that's pretty sad, too.
House Of Wood - Mandrill (has me in tears by the end of the second verse no matter HOW many times I hear it).
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