#268 The Twelve Most Depressing Songs..... Ever! 1. Richard Thompson - The End Of The Rainbow 2. George Michael - Careless Whisper 3. Ben Folds - Brick 4. Eric Clapton - Tears in Heaven 5.The Hollies - He ain't heavy, He's my Brother. 6. Miles Davis - Time After Time 7. 8. 9. 10. 11. 12.