25 Of The Saddest Songs I Ever Heard
1. I Can't Make You Love Me - Bonnie Raitt
“Turn down the lights; turn down the bed. Turn down these voices inside my head/ Lay down with me, tell me no lies: just hold me close - don't patronize. Don’t patronize me.”
2. Brick - Ben Folds Five
“She’s a brick and I’m drowning slowly – off the coast and I’m heading nowhere. She’s a brick, and I’m drowning slowly.”
About: His teenage girlfriend's abortion the day after Christmas.
3. Angie - The Rolling Stones
“Angie…Angie…when will those clouds all disappear? Angie…Angie… where will it lead us from here? With no loving in our souls and no money in our coats, you can’t say we’re satisfied…but Angie…Angie, you cant say we never tried.”
About: Love as a casualty of poverty and time.
4. Fast Car - Tracy Chapman
“You got a fast car; I want a ticket to anywhere. Maybe we make a deal - maybe together, we can get somewhere.”
About: A first, foolish love that serves as an escape, but quickly turns into a prison of its own.
5. Dress Blues - Jason Isbell of the Drive-By Truckers
“Your wife said this all would be funny when you came back home in a week.
You'd turn twenty-two and we'd celebrate you in a bar or a tent by the creek.
Your baby would just about be here, your very last tour would be up; but you won't be back. They're all dressing in black, drinking sweet tea in styrofoam cups.”
About: Jason Isbell's high school friend, Matt Connolly, who died in the Iraq War. An evocative vision of the destruction of life, sung beautifully in the heart of patriotic Texas.
6. Romeo & Juliet's Theme - Henry Mancini
7. On My Block – Tupac
“Teardrops and closed caskets - the three strikes law is drastic, and certain death for us ghetto bastards; what can we do when we're arrested but open fire? Life in the pen ain't for me, cause I'd rather die…but don't cry through your despair - I wonder if the Lord still cares for us niggas on welfare?”
About: Poverty destroys, and nobody helps or even seems to care.
8. Wonderwall – Oasis
“And all the roads we have to walk along are winding, and all the lights that lead us there are blinding - there are many things that I would like to say to you…but I don't know how.”
About: According to Noel Gallagher, "an imaginary friend who's gonna come and save you from yourself."
9. Hallelujah - Rufus Wainwright
“Maybe there's a God above, and all I ever learned from love was how to shoot at someone who outdrew you. It's not a cry you can hear at night, it's not somebody who's seen the light, it's a cold and it's a broken hallelujah.”
About: God & Love. One and the same, equally powerful and equally painful.
10. Don't Fear the Reaper - Blue Oyster Cult
“All our times have come here but now they're gone…Seasons don't fear the reaper;
nor do the wind, the sun or the rain. We can be like they are…”
About: A murder-suicide pact made between lovers. Although the band itself says the song is about "the transcendence of love beyond the physical realm."
11. Highwayman - The Highwaymen
“I was a highwayman. Along the coach roads I did ride, with sword and pistol by my side. Many a young maid lost her baubles to my trade; many a soldier shed his lifeblood on my blade. The bastards hung me in the spring of twenty-five - but I am still alive.”
About: The eternal ghost of the western highwayman; the ever-living spirit of the dead and forgotten; the bloody legacy of the American West.
12. The Weakness In Me - Joan Armatrading
“Why do you come here, when you know I've got troubles enough?
Why do you call me, when you know I can't answer the phone?
And make me lie when I don't want to,
And make someone else some kind of an unknowing fool?
Make me stay when I should not?
If you're so strong then resolve the weakness in me.”
About: The one who always seems to get to you.
13. Seasons of Love – RENT
“525,600 minutes - 525,000 moments so dear. 525,600 minutes…how do you measure, measure a year? In daylights, in sunsets, in midnights, in cups of coffee? In inches, in miles, in laughter, in strife? In…525,600 minutes…how do you measure a year in the life? How about love? How about love? How about love? Measure in love. Seasons of love.”
About: From Rent; considering the multitude of ways in which we chop up and measure our lives; giving value to each moment of our lives. Also reminiscent of Paul Bowles' The Sheltering Sky: "But because we don't know, we get to think of life as an inexhaustible well. Yet everything happens a certain number of times, and a very small number, really. How many more times will you remember a certain afternoon of your childhood, some afternoon that's so deeply a part of your being that you can't even conceive of your life without it? Perhaps four or five times more. Perhaps not even. How many more times will you watch the full moon rise? Perhaps twenty. And yet it all seems limitless."
14. If We Hold On Together (Theme Song from Land Before Time) - Diana Ross
“When we are out there in the dark, we'll dream about the sun. In the dark, we'll feel the light. Warm our hearts, everyone…if we hold on together, I know our dreams will never die. Dreams see us through to forever - as high as souls can fly, the clouds roll by for you and I.”
About: In The Land Before Time, this song and a single treestar (read: leaf) are all Littlefoot has left of his dead mother, who died sacrificing herself to save him from a predator.
15. Abraham, Martin, and John – Dion
“Didn't you love the things that they stood for? Didn't they try to find some good for you and me? And we'll be free…some day soon, and it's a-gonna be one day ...”
About: Abraham Lincoln, Dr. Martin Luther King, Jr., John F. Kennedy and Robert F. Kennedy. Written after the assassinations of Dr. King and the President Kennedy in April and June 1968.
16. Somewhere Out There - An American Tail
“And even though I know how very far apart we are, it helps to think we might be wishing on the same bright star. And when the night wind starts to sing a lonesome lullaby, it helps to think we're sleeping underneath the same big sky.”
About: Fievel has been separated from his family, and although she cannot see him, his sister sings this lullaby to give him comfort on a lonely night.
17. Heaven (9/11 Remix) - DJ Sammy
“Oh, thinking about all our younger years, there was only you and me.
We were young and wild and free. Now, nothing can take you away from me - we’ve been down that road before, but that's over now.”
About: Actually, this is just a wack slow ballad. But then somebody mixed in tapes of people's last wishes to their families who died in the World Trade Center attack. And it tears your heart out.
18. Fields of Gold - Eva Cassidy
“I never made promises lightly, and there have been some that I’ve broken. But I swear in the days still left, we’ll walk in fields of gold.”
About: Ostensibly, a walk through a field with a departing lover. But this is one of Eva Cassidy's last recorded songs before her death of melanoma in 1996, and it is poignant with the presence of her.
19. Strange Fruit - Billie Holiday
“Southern trees bear strange fruit: blood on the leaves and blood at the root. Black bodies swinging in the southern breeze. Strange fruit hanging from the poplar trees.”
About: Lynchings in the Jim Crow South. Dead bodies dangle from trees - strange fruit.
20. Tha Crossroads - Bone Thugs N Harmony
“Can somebody, anybody tell me why? Hey, can somebody, anybody tell me why we die, we die? I don’t wanna die, no…but I’ll see you at the Crossroads, so you won’t be lonely...”
About: About death; a tribute to those who have passed on. What makes this song hit you is hearing a grown man plead like a little child to have his dog back in verse three, and again in the verse quoted above.
21. Sister Golden Hair Surprise – America
“Well, I keep on thinkin’ bout you, Sister Golden Hair Surprise. And I just cant live without you; cant you see it in my eyes? Now, I been one poor correspondent - I been too, too hard to find; but it doesn’t mean you ain’t been on my mind…”
About: A man who intends to go and get his lover back, but finds he just can't seem to make it out the door before depression takes him back.
22. Runnin' (Dyin' to Live) – Tupac
“You know, I wonder if they'll laugh when I am dead. Why am I fighting to live, if I'm just living to fight? What am I trying to see when there ain’t nothing in sight? Why am I trying to give when no one gives me a try? Why am I dying to live, if I'm just living to die?”
About: Trying to survive in the deathtrap of the ghetto, with no hope, no dreams, and no one who believes in you. Recorded after Tupac Shakur's death by drive-by in 1996.
23. The Freshman - Verve Pipe
“My best friend took a week's vacation to forget her. His girl took a week's worth of valium and slept, and now he's guilt stricken, sobbin' with his head on the floor - thinks about her now and how he never really wept; he says: ‘I can't be held responsible. 'Cause she was touching her face. I won't be held responsible - she fell in love in the first place.’”
About: A pair who suffer through an awful abortion; the girl kills herself in guilt, and her boyfriend and their friends rally together to try to (not) forget her. Brian Vander Ark wrote this song about the guilt he felt over his own ex-girlfriend's abortion.
24. If You Love Me - B. B. King
“If you love me, you will know the truth - I wasn’t born to lose. And I love you.”
About: Love. But listening to B. B. King and Van Morrison wail together on this short, dignified piece gives entirely new dimension to what could just be a lifeless ballad.
25. Levon - Elton John
“Levon sells cartoon balloons in town; his family business thrives. Jesus blows up balloons all day, sits on the porch swing watching them fly. And Jesus, he wants to go to Venus, leaving Levon far behind…Take a balloon and go sailing while Levon, Levon slowly dies.”
About: Jesus' father and grandfather, reimagined in modern day, and the tensions that exist in their lives.