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The Saddest Songs of All-Time

  • Oct 28, 2010
Every so often I enjoy creating a list of songs revolving around a certain subject or theme. I thought it might be kinda neat to put together a list of what I consider to be the saddest songs of all-time. Here is a group of songs covering a wide range of genres and a number of different era.s For the most part, they are presented for your consideration in no particular order. Let me know what you think and at the same time, if you are so inclined, I invite you to make up your own list and add it to the "Music Matters" community here on Lunch.
A real tear jerker from one of the great voices in the history of rock and roll.
At Seventeen
You can just hear the pain in Janis Ian's voice. It's what life is really like for lots of teenage girls.
A song by Little Anthony and the Imperials
One of the great doo-wop sounds of all time by Little Anthony and the Imperials. From 1958.
He Stopped Loving Her Today
The title says it all. For my money this is the saddest song of all-time If you have never heard it I urge you to sample it on YouTube.
End Of The Road
A huge hit for Boyz II Men ......breaking up is very hard to do.
She's Leaving Home
From the album that many consider to be the greatest of all-time "Sgt. Pepper's Lonely Hearts Club Band" The sad story of a misundersood teenage girl about to leave home. Her parents just don't understand!
Hurt (cover)
Johnny Cash covered this Nine Inch Nails tune back in 2002. Some consider this to be the saddest song ever.
Cry Me A River
A huge hit for torch singer Julie London way back in 1955. Later covered by Joe Cocker in the late 1960's.
Love Hurts
Essentially a one-hit wonder, the group Nazareth covered this Everly Brothers tune back in 1975. I think we can all relate to this one.
Vincent (Starry, Starry Night)
Memorable and haunting song about the artist VIncent Van Gogh. From 1972
How Do I Live
Country singer Leann Rimes had a huge crossover hit with this one in 1997. Again, feel the pain iand the despair in her voice.
Are You Lonesome Tonight?
Do you miss me? I hope you do 'cause I sure miss you. Are you miserable like I am or have you found someone new? A break-up can be devastating.
Two Out Of Three Ain't Bad
I really do hate to have to tell you this but I enjoy being with you, I am very attracted to you but you are not the love of my life. I wish I felt differently but I don't. Don't worry, you'll get over it in time.
Tears in Heaven by Eric Clapton
Eric Clapton agonizing over the loss of his child in a tragic accident. I have read where this is one of the songs that even makes men cry.
Last Kiss
Whether you prefer Pearl Jam's version from the late 1990's or the original by J. Frank Wilson and the Cavaliers from 1958 this one is a real tear-jerker. We can all imagine ourselves in such a horrible situation and just pray that it never actually happens to us.
Send In The Clowns
This haunting Stephen Sondheim tune has been recorded by many artists. The most notable version was by Judy Collins.
I'm So Lonesome I Could Cry
One of the greatest country tunes ever written. It turns out Hank Williams was singing about himself when he recorded this one back in 1949. Hank certainly did not have a great voice but he wrote some amazing tunes during his tragically short life.
Goodbye To Love
I would have to say that this is my favorite song by the popular 1970's brother-sister duo The Carpenters. Just dripping with self-pity. Yeah, I have been there and I totally related to this one when it hit the charts.
This Used To Be My Playground
From one of my favorite films "A League of Their Own". It's a song about revisiting your past and thinking about the hopes and dreams you had back then. Now you realize that much of what you had hoped for is never going to happen. I guess this happens to all of us. A very moving song.
It's the most recorded song of all-time and with good reason. Yesterday everything was wonderful....life was good! But then you went away and now my world has been turned upside down. I still don't understand. You told me you are not coming back. Now I am longing for yesterday. One of the greatest Lennon-McCartney tunes ever.
It's Over
No list of saddest songs would be complete without this Roy Orbison gem from 1964.
You Don't Bring Me Flowers
Barbra Streisand and Neil Diamond are in a melancholy mood. The bloom is off the rose now and their relationship has settled into the same old dull routine. The magic is gone and now both wonder if they have a future together.
Someone That I Used To Love
I think this tune ranks right up there with "He Stopped Loving Her Today" as one of the saddest songs ever recorded. It is about that moment when a person comes to the conclusion that they just don't love someone anymore. It might be a young teen or it could be an adult who is coming to this realization after years of marriage. A devastatingly beautiful song!
Concrete Angel
A powerful ballad focusing on the issue of child abuse.
Eleanor Rigby (Song)
A song about death and loneliness. This tune was a real departure from the high-energy, upbeat fare being offered by The Beatles in 1966, A classic!
Total Eclipse Of The Heart
"Once upon a time I was falling in love, now I'm only falling apart". The love of her life has gone away and now all is lost. A haunting melody and terrific music only add to the impact of this incredibly depressing tune.
Alone Again (Naturally)
A smoving song about coping with broken relationships and the loss of people close to us.
Hurt So Bad
Another powerful tune from Little Anthony and the Imperials, this time from 1965. Little Anthony makes no bones about it. Just seeing her again is a very painful experience. Things have been going great for her but he is still stuck on her something terrible. His pleas for her to come back to him fall on deaf ears and it "Hurts So Bad". The desperation in his voice is stunning!
The End Of The World
Country singer Skeeter Davis had a huge crossover hit back in 1963 with this one.

What did you think of this list?

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December 05, 2010
I've only heard about a third of this list but it is certainly inspiring. I think I might get an idea to kick off a list of that nature! Cool! Thanks, Paul!
November 03, 2010
Cats in the Cradle is certainly one of the first songs that came to mind. Interesting list - there are a lot of sad songs out there!
November 01, 2010
Nice list! I'm glad to see you put Johnny Cash's version of "Hurt" on here. That's quite possibly one of the greatest recordings of the last fifty years in my book.
November 01, 2010
Great idea for a list, Paul. Very interesting. As a Hendrix fan, I would put "Hey, Joe" and "Castles Made of Sand" in there somewhere.
November 01, 2010
Great list Paul. Actually, the biggest tear jerker for me still is Honey by Bobby Goldsboro. I can't listen to it without getting misty eyed. At Seventeen is very appropos today with all the bullying that is going on in school. Alone Again Naturally is up there (the line I remember I cried when my father died gives me chills) and The Living Years (telling your father everything you need to say while he is still alive) . Then there is Minny Ripperton's Loving You. The line "stay with me when we grow old" always got to me since she died of cancer shorty after the song came out.
About the list creator
Paul Tognetti ()
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I guess I would qualify as a frustrated writer. My work requires very little writing and so since 1999 I have been writing reviews on non-fiction books and anthology CD's on amazon.com. I never could … more
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