Most Melancholy Songs

PetSounds
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 Fields of Gold - Sting
5 Tears in Heaven - Eric Clapton

Great List Spencer! I couldn't even choose. There are so many great songs here. - Beatlesboy9

6 Catch the Wind - Donovan
7 Black Star - Yngwie
8 Bitter Green - Gordon Lightfoot
9 As Tears Go By - The Rolling Stones
10 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.

The Contenders

11 The Dangling Conversation - Simon and Garfunkel
12 The Long and Winding Road - The Beatles
13 Beyond the Realms of Death - Judas Priest
14 Hey You - Pink Floyd
15 Caroline No - The Beach Boys
16 Black Hole Sun - Soundgarden
17 Walk Away Renee - The Left Banke
18 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

19 My Last Sunrise - Demons & Wizards
20 Bridge of Sighs - Robin Trower
21 Voice of the Soul - Death
22 Time Stood Still - Madonna
23 Fade to Black - Metallica
24 Friends of Mine - The Guess Who
25 Un-break My Heart - Toni Braxton
26 Walkaway - Geri Halliwell
27 Fiddler on the Green - Demons & Wizards
28 Wake Me Up When September Ends - Green Day
29 Wicked Game - Chris Isaak
30 Yesterday - The Beatles
31 Back On the Street Again - Sunshine Company

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

32 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

33 This Used to Be My Playground - Madonna
34 Everytime - Britney Spears
35 Confessions of a Broken Heart (Daughter to Father) - Lindsay Lohan
36 Because of You - Kelly Clarkson
37 Illegal - Shakira
38 Anybody There? - Rainbow
39 Down Where I Am - Demons & Wizards
40 Season of the Witch - Vanilla Fudge
41 Talking in Your Sleep - Gordon Lightfoot
42 Fire and Rain - James Taylor
43 All of Me - John Legend

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

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

48 I Can't Make You Love Me - Bonnie Raitt
49 1979 - Smashing Pumpkins
50 Beware of Darkness - George Harrison
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List Stats

200 votes
67 listings
4 years, 102 days old

Top Remixes (4)

1. The Rains of Castamere - Jackie Evancho
2. Open Fields of Grace - Jackie Evancho
3. To Where You Are - Jackie Evancho
BobG
1. Hey You - Pink Floyd
2. Black Star - Yngwie
3. Beyond the Realms of Death - Judas Priest
Metal_Treasure
1. Fields of Gold - Sting
2. Catch the Wind - Donovan
3. Bitter Green - Gordon Lightfoot
PetSounds

WRemix
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