Most Melancholy Songs

The definition of melancholy, according to the Oxford Dictionary, is "deep and long-lasting sadness".
The Top Ten
1 The Rains of Castamere - Jackie Evancho

This to me sets the stage for the scene like no other song!

She captures my heart, she is a gift to the world.

My goodness, what a lot of Jackie Evancho fans there are!

Mournful, dreary, haunting... Sounds just like rain!

2 Open Fields of Grace - Jackie Evancho

Beautiful lyrics about loss and hope, exquisitely delivered by Jackie's soaring soprano voice.

From her "Awakening" album.

3 To Where You Are - Jackie Evancho

This song will resonate with anyone who is missing someone.

4 Black Star - Yngwie
5 Fields of Gold - Sting
6 As Tears Go By - The Rolling Stones
7 Catch the Wind - Donovan
8 Dance the Night Away - Cream

If any song can be excellent psychedelic blues-rock and at the same time be melancholy, this is the one.

9 Tears in Heaven - Eric Clapton

Great List Spencer! I couldn't even choose. There are so many great songs here.

10 Bitter Green - Gordon Lightfoot
The Contenders
11 Hey You - Pink Floyd
12 The Dangling Conversation - Simon and Garfunkel
13 Beyond the Realms of Death - Judas Priest
14 The Long and Winding Road - The Beatles
15 Black Hole Sun - Soundgarden
16 Walk Away Renee - The Left Banke
17 Caroline No - The Beach Boys
18 My Last Sunrise - Demons & Wizards
19 Bridge of Sighs - Robin Trower
20 Voice of the Soul - Death
21 Walk Away - Matt Monro

This song broke my heart again and again some months ago, but I couldn't stop playing it. Now I hope I never hear it again, my heart couldn't stand it, even though the song is just so beautiful.

22 Fade to Black - Metallica
23 Friends of Mine - The Guess Who
24 Time Stood Still - Madonna
25 Fiddler on the Green - Demons & Wizards
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