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

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

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

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

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

2 Open Fields of Grace - Jackie Evancho

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

From her "Awakening" album.

3 To Where You Are - Jackie Evancho

This song will resonate with anyone who is missing someone. - BobG

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. - Beatlesboy9

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. - Britgirl

22 Fade to Black - Metallica
23 Friends of Mine - The Guess Who
24 Time Stood Still - Madonna
25 Fiddler on the Green - Demons & Wizards
26 Un-break My Heart - Toni Braxton
27 Walkaway - Geri Halliwell
28 Anybody There? - Rainbow
29 Season of the Witch - Vanilla Fudge
30 Wake Me Up When September Ends - Green Day
31 This Used to Be My Playground - Madonna
32 Everytime - Britney Spears
33 Confessions of a Broken Heart (Daughter to Father) - Lindsay Lohan
34 Because of You - Kelly Clarkson
35 Illegal - Shakira
36 Down Where I Am - Demons & Wizards
37 Wicked Game - Chris Isaak
38 Yesterday - The Beatles
39 Back On the Street Again - Sunshine Company

"Once I used to think that the world belonged to me,
Now it belongs to someone else."

40 If You Could Read My Mind - Gordon Lightfoot

Actually, this song has been done by quite a few artists.

Yes it has, but Gordon wrote it. - PetSounds

41 My Immortal - Evanescence
42 Talking in Your Sleep - Gordon Lightfoot
43 Fire and Rain - James Taylor
44 All of Me - John Legend

Says everything you want to say when you can't speak. - Britgirl

45 Wooden Ships - Crosby, Stills, Nash & Young
46 Things I'd Like to Say - The New Colony Six
47 Here Without You - The Byrds
48 Donna Donna - Donovan

Originally a song of the Jewish resistance to Nazi atrocities, it was first introduced to the popular consciousness by Joan Baez, but Donovan's version is the most melancholy.

49 I Can't Make You Love Me - Bonnie Raitt
50 1979 - Smashing Pumpkins
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