19. Sinead O'Connor Nothing Compares 2 U http://youtu.be/iUiTQvT0W_0 The saddest song ever? Quite possibly. I double-doggy-dare you to listen to it when heartbroken, or even when suffering one of those particularly emotional hangovers. Don't tell me you come away feeling all kinds of those feels. Hell, watch the video if that doesn't do it; when she starts crying, you're dead inside if you feel nothing. This may originally be a Prince song, but Sinead O'Connor completely made this song her own, and in doing so created perhaps one the ultimate breakup song because sometimes we don't want to feel better, we want to feel all the sad.
18. Chris Isaak Wicked Game
http://youtu.be/PGlfpzRL2O0 Perhaps the coolest sounding heartbreak ever? Definitely maybe. Isaak broods his pained croon all over a slow burning and sorrowful ballad, drenched in Americana. It took featuring on the soundtrack to David Lynch's Wild At Heart for this song to really hit its stride of popularity. It's hard to see why as it perfectly captures the unrequited love of a one-sided breakup. Lyrically capturing that initial burst of passion 'I never dreamed that I'd meet somebody like you', quickly followed by the pained realisation 'And I never dreamed I'd lose somebody like you.' The result is the lyrics battling with wanting to still fall in love with this person, and not wanting to fall in love at all. The song closes on the bitter, and ominous, 'nobody loves no one.'