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 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
PSearch List

Related Lists

Top 10 Most Melancholy Rock and Metal Songs Best Melancholy of Haruhi Suzumiya Characters Top 10 Most Annoying Songs Ever Top Ten Most Inspirational Songs of All Time Most Underrated Metallica Songs

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
1. Hey You - Pink Floyd
2. Black Star - Yngwie
3. Beyond the Realms of Death - Judas Priest
1. Fields of Gold - Sting
2. Catch the Wind - Donovan
3. Bitter Green - Gordon Lightfoot

View All 4

Error Reporting

See a factual error in these listings? Report it here.