Most Hauntingly Beautiful and Sad Songs

The Contenders: Page 2

21 Wake Me Up When September Ends - Green Day

Billie Joe has the innate ability to write songs that are relatable and almost haunting in their true nature. Wake Me Up When September Ends is a perfect example of what he can do as a songwriter, not just as the punk rock frontman of a world famous rock band to which many people dismiss him as mediocre. But he's not. He is a talent Just by opening up about a part of his life that he had not displayed prior, he really came through and proved just how valuable his is as an artist. RIP Andrew Armstrong.

This song is about the death of Billie Joe's father. Is such an emotional song, with such beautiful lyrics. - georgielikesgreenday

I cry every time I listen this song. Beautiful.

Billie Joe's father died on September 1st 1982. Billie, age 10, camped in his room in deep depression, his mother and siblings begging him to come out, the response to which always was: "Wake Me Up When September Ends" - AFL

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22 Hurt - Nine Inch Nails

It's sadder than the Johnny Cash cover. How he whispers most of the song. You can feel the pain. - MEparandriod

The lyrics and the emotion in his voice are just so raw they make me cry when I listen to it.

23 Hello - Evanescence

Should Be number 1 - mood333

I love it, I love her voice, it's like har voice makes her voice makes me even more sad.

Playground school bell rings again
Rain clouds come to play again
Has no one told you she's not breathing?
Hello, I am your mind giving you someone to talk to
Hello

If I smile and don't believe
Soon I know I'll wake from this dream
Don't try to fix me, I'm not broken
Hello, I am the lie living for you so you can hide
Don't cry

Suddenly I know I'm not sleeping
Hello, I'm still here
All that's left of yesterday

24 A Little Bit of Everything - Dawes
25 Rains of Castamere - Jackie Evancho

Jackie Evancho demonstrates time and again there is no one that can compare with the awesome beauty of her voice. Simply outstanding.

Mesmerized for days since this was released.. on replay for hours.. under a spell.. can't stop listening..

Up, Jackie! You're the best!

Now THIS song is much sadder than "Nella Fantasia." Pride goeth before a fall, that's the tragic message of this song from Game of Thrones. Jackie's voice gives the song a haunting, mournful quality. - BobG

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26 (I Can't Get No) Satisfaction - Rolling Stones

It's a song about a guy who can't get laid. There is nothing more sad.

27 Fields of Gold - Eva Cassidy

Ever's voice is truly angelic. The way she covered this song is phenomenal! Such a beautiful and calming version of fields of gold. Love love love...

Such an amazing voice! Haunting.

28 Hurt - Christina Aguilera
29 A Place Only You Can Go - Needtobreathe
30 Nothing Compares 2 U - Sinead O'Connor
31 I Just Don't Think I'll Ever Get Over You - Colin Hay
32 Elizabeth on the Bathroom Floor - Eels

This song is simply amazing. The lyrics are so simple, but leave you thinking about their meaning for hours. Especially when you learn that he wrote the song for his sister Elizabeth, who killed herself after a long battle with depression. Such a hauntingly beautiful song.

Short song with long lasting effects. Its about the singers sister during her last moments before killing herself. The eerie electric guitar is like a creepy lullaby.

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33 Adrian - Jewel

This tune is practically the definition of a "haunting, beautiful and sad song."

34 Born to Die - Lana del Ray

This song is not just sad. It is a powerful moment to share with Lana, who's such an underrated artist.

Such a great song from a very talented woman.

Only 52? Why? This is a great song, & very sad. - Fan_of_Good_Music

35 Nights in White Satin - The Moody Blues

This is so magical and haunting and I don't quite know why but it does make me have goose bumps after all those years (I'm 57 tomorrow! ) But to me if you don't feel joy or sadness or want to leap around listening to a song then it's almost not worth listening too. I suppose if it's a 'relaxing' tune then it's different!
Totally agree about the line where they sing 'Letters I've written, never meaning to send'...After my divorce sixteen years ago I wrote so many letters and never ever sent them but I did notice as time went by, my letters were less and less angry and bitter and they also became more fair and understanding...it must have been therapeutic for me. I do have to giggle a little because I was quite young then this group were around and unless we saw the actual album we didn't see names of artists or songs spelt out so I thought it was 'Knights' in White Satin,' which is a little bit of a ridiculous image! Sorry one and all if I've ruined the magic! :) But this song will ...more

The beginning of this song almost made me turn it off, but the moment I hit the chorus I was enthralled with the violin, singing and drama of the whole song. "Just what I'm going through they can't understand" Lyrics that would be cliche in any other song, but not in this one. And of course the wonderful flute only adds to the songs appeal.

The most beautiful, haunting, song ever written. There is no comparison by any other group who write their own material.

So haunting it doesn't seem real.

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36 Stairway to Heaven - Led Zeppelin
37 Everything Means Nothing to Me - Elliott Smith

Definitely was a hard decision to pick between this song and "How To Disappear Completely". In the Radiohead song, the part that always gives me chills is at the end when it almost sounds like he's crying, "I'm not here - this isn't happening. " But in this song... Geez. It's so... Yeah, hauntingly beautiful. Damn eerie. Elliott Smith was the master of hauntingly beautiful songs.

The first time I heard this it conjured such an image that I can still recall it vividly. The back story is also just as striking as the song.

This song is all consuming, making you spiral down into a reality that stops existing the second the song stops. Needle in the hay is worth a mention too

38 Forgiven - Within Temptation

Wonderful wonderful song. Amazes me not more people know of this wonderful song and its not more popular and well known

Great song, I also think Our Farewell, Memories & Say My Name are excellent sad songs with meaningful lyrics.

Talks of love and loss and the strength to move on.

39 Broken - Jake Bugg
40 Mad World - Michael Andrews

This is the most hauntingly beautiful song I have ever heard. The first time I ever heard this was when I was like 9. I was watching Smallville and this song came on at the end of the episode. I have never been more entranced by a song in my life.

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List StatsUpdated 18 Aug 2017

2,000 votes
371 listings
6 years, 245 days old

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