TOP FIVE: Most Heartbreaking Songs Of The Last 20 Years

Jun 27 '01    Write an essay on this topic.


The Bottom Line I hope you enjoy this Top Five. If you have anything to add, please post your comments.

Probably since the beginning of time, music has been used as a means to vent the heartbreak and frustration of a relationship gone wrong, a relationship that never happened to begin with, or just bad love in general.
Some of the best songs ever written have been sad ones. The Beatles mined this territory. So did Bob Dylan, and numerous other great writers. It's a great situation - not only is it therapeutic for a writer to let those extreme emotions out, but he or she is helping other people to feel better in the process.

These are the songs that have made me cry.

5. Missing, Everything But The Girl
I'm referring to the album version of this song - the remix almost completely obliterated the extreme longing evoked by the lyrics. Listening to this song, one wonders if the time that the protagonist and her long lost love spent together was just a dream...
Key lyric:
And the years have proven
to offer nothing since you moved.
You're long gone
but I can't move on,
And I miss you;
Like the deserts miss the rain.


4. I Know It's Over, The Smiths
Morrissey is known for writing about pain, but he never was more poetic, never sang with more conviction, than on this song. The composer and arranger of the song, Johnny Marr, must have known that the spotlight here belonged to Morrissey alone - though the band ebbs and flows with his crescendos, the overdubs are kept to a bare minimum. This song is so incredibly intense, I sometimes have to program it out when I listen to the album.
Key lyric:
Why do you sleep alone tonight?
I know...
'Cause tonight is just like any other night
That's why you're on your own tonight
With your triumphs and your charms
While they're in each other's arms...


3. Brick, Ben Folds Five
I know there must be others, but this is the only song I know of that deals with abortion. Brick tells the story of an abortion that tears a young couple apart - even though they are in love.
Key lyric:
As weeks went by
It showed that she was not fine
They told me son, it's time to tell the truth
And she broke down, and I broke down
'Cause I was tired...
Of lying.
Driving back to her apartment
For the moment, we're alone.
She's alone, and I'm alone.
Now I know it.


2. Goodnight Elisabeth, Counting Crows
It was so, so tough to decide which order the #1 and #2 songs should be placed in, but in the end I decided against this song. Nobody sings a song with more conviction than Adam Duritz, because his lyrics reflect his own life. If I had to guess, I believe this song is about a woman that Adam Duritz fell in love with - but the relationship was doomed because he was born to be a musician. Every girl he meets in every city just might be the next Elisabeth, he thinks, but he always ends up missing her just the same. She may be the most incredible thing in California, he says - but he is the King of the Rain, destined to fall everywhere. And he wishes that she could be the same (Won't you fall down on me now?). Pure poetry.
Key lyric:
I will wait for you in Baton Rouge
Miss you down in New Orleans
Wait for you while she slips into something comfortable
I'll miss you when I'm slipping in between
If you wrap yourself in daffodils
I will wrap myself in pain
And if you're the queen of California
Baby, I am the King of the Rain.
And I say goodnight, Elisabeth.


It was so close, and really either of these songs can be number one for me depending upon how I feel - but here's the one I picked...

1. God Give Me Strength, Burt Bacharach and Elvis Costello
The best song from possibly the best album about heartbreak ever made. When you pair one of the world's best living composers with one of the world's best living poets, you're bound to make magic. They compliment each other perfectly. This song's climax is simply not to be missed. It makes the hair on the back of my neck stand up every single time. Costello fills the song vocally with light and shade, and phrases his lyrics as well as Frank Sinatra ever could.
Key lyric:
God if she'd grant me her indulgence and decline
I might as well wipe her from my memory
Fracture the spell
As she becomes my enemy
Maybe I was washed out like a lip-print on his shirt
See, I'm only human... I want him to hurt
I want him to hurt.


Honorable Mention
These songs do deserve mention as true heartbreakers. They just don't deserve a place in the Top Five, because I decided to narrow the list to songs that deal with love.

Everybody Hurts, REM
Deals with: Suicide.

Ana's Song (Open Fire), Silverchair
Deals with: Eating Disorders.

Last Kiss, Pearl Jam (originally by J. Frank Wilson and the Cavaliers)
Deals with: Death of one's love.

Holding Back The Years, Simply Red
Deals with: I'm not sure. This song strikes me as being about a person who escaped from an abusive father at a young age, and realized later in life how little he'd been able to heal.

Wonderful, Everclear
Deals with: Being a child in a broken family.

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