(Pictured: Benny, Frida, Agnetha, and Bjorn, on stage in 1979.)
Back in 2012, it was reported that science had determined Adele’s “Someone Like You” to be the near-perfect sad song. In 2013, Rolling Stone published the results of a reader poll that chose the 10 saddest songs of all time, including George Jones’ “He Stopped Loving Her Today” and John Prine’s “Sam Stone,” “Cat’s in the Cradle” by Harry Chapin, and Eric Clapton’s “Tears in Heaven,” which clocked in at #1. In 2015, Paste cast the net a little bit wider, picking 50, and it caught some good ones: several from the Rolling Stone list plus “D-I-V-O-R-C-E” by Tammy Wynette, “Whiskey Lullaby” by Alison Krauss, and Bruce Springsteen’s “The River,” among others.
My personal picks for saddest songs ever are not on either list, and on the flip. (Please add your favorites in the comments.)
ABBA’s music was often deeper than it got credit for being, and the existentially bleak 1980 single “The Winner Takes It All” is the best example:
The gods may throw a dice
Their minds as cold as ice
And someone way down here
Loses someone dear
And later:
But tell me does she kiss
Like I used to kiss you
Does it feel the same
When she calls your name
Somewhere deep inside
You know I miss you
But what can I say
Rules must be obeyed
The judges will decide
The likes of me abide
Spectators of the show
Always staying low
Human beings as pawns in some cosmic game of chance is not exactly your usual pop-song material.
You can’t fully appreciate “The Winner Takes It All” from the page—you need to hear it. Even better, watch the video, directed by Swedish filmmaker Lasse Hallström. The contrast between shots of happy couples and the resignation in Agnetha Faltskog’s voice, and the hurt on her face, is powerful. In “The Winner Takes It All,” the fragility of human feelings is no match for the enormity of fate, and the feelings of pain and helplessness are devastating.
Down a YouTube rabbit hole the other day, I came across another candidate for saddest song ever, one that I’d forgotten about.
Nashville contract songwriting frequently works like this: a producer gives the writers a title or concept and tells them which artist it’s intended for. Then it’s up to the writers to fill the order. (Which explains a lot about the mediocrity of so much Nashville product, in days of yore right up to the present.) Improbable as it seems, this industrialized process manages to create art, sometimes. The greatest of the contract songwriting teams will often say, however, that their favorite compositions are their most personal.
So it was for Kye Fleming and Dennis Morgan, who would end up the most prolific and successful Nashville team of the early 80s. They had already written the #1 hit “Sleepin’ Single in a Double Bed” for Barbara Mandrell in 1978. Their composition “Years” wasn’t intended as a single until radio stations started playing it from Mandrell’s album One for the Record late in 1979. In February 1980, it made #1 on the Billboard country chart. (Wayne Newton rushed out a pop version that made #35 on the Hot 100, but Mandrell’s version is the one you want. )
Faded photographs
The feelings all come back
Even now sometimes you feel so near
And I still see your face like it was yesterday
It’s strange how the days turned into years
It’s not just the words and music that make “Years” what it is. Barbara Mandrell really sells it. We default to the idea that she’s singing about a lover who has left her, but she could just as easily be missing someone who’s died. Whichever it is, she’s been fighting her grief for a long time, and in her weariness she sometimes simply gives in to it:
After all this time
You’d think I wouldn’t cry
It’s just that I still love you
After all these years
And finally:
Nighttime gently falls
Another day is gone
I turn around to find you’re still not here
I’ll leave the hall light on
In case you come back home
But I’ve been saying that for years
We hear it over and over: “Time heals all wounds.” We say it to others, and we tell it to ourselves. Often, the only thing that gets us through a particular today is the knowledge that we’ll feel better on some future day. But what if time doesn’t do what it’s supposed to do?
The Hits Just Keep On Comin' 
Here’s a baker’s dozen, off the top of my head, JB.
“Traces” — Classics IV
“Worst That Cold Happen” — Brooklyn Bridge
“Everything I Own” — Bread
“’til I Die” — Beach Boys
“It’s Too Late” — Carole King
“I Can’t Make You Love Me” — Bonnie Raitt
I’m So Lonesome I Could Cry — Hank Williams / B.J. Thomas
“Alone Again (Naturally)” — Gilbert O’Sullivan
“Never Gonna Fall In Love Again” (trumping his “All By Myself”) — Eric Carmen
“The Grand Tour” (which bests “He Stopped Loving Her Today” for me) — George Jones
“Since I Lost My Baby” — Temptations
“I Just Don’t Know What To Do With Myself” — Dusty Springfield (absolutely the best version)
“Eleanor Rigby” — Beatles
Your mention of “The Grand Tour” caused me to flash on “A Good Year for the Roses,” another terribly sad George Jones record, which was covered by Elvis Costello, I believe.
Good choice, JB.
Now you want depressing? Think the Cure, Leonard Cohen, Merle Haggard, Billie Holiday (especially “Strange Fruit” and the “Lady in Satin” album), the third Big Star album, etc.
Now that I’ve got you bummed out, let me give you the coup de grace, “Jeannie’s Afraid of the Dark” by Dolly Parton and Porter Waggoner
JB: “We hear it over and over: “Time heals all wounds.” We say it to others, and we tell it to ourselves. Often, the only thing that gets us through a particular today is the knowledge that we’ll feel better on some future day. But what if time doesn’t do what it’s supposed to do?”
Read that over the intro to this. I guarantee you’ll hit the post:
“Time In A Bottle” by Jim Croce
“Long, Long Time” by Linda Ronstadt
“Cherish” by the Association
And perhaps not quite in the same league:
“Misty Blue” by Dorothy Moore
“One Less Bell To Answer” by the 5th Dimension
“For No One” by the Beatles
I should add “You’re Missing” by Bruce Springsteen.
Walter Brennan’s “Old Rivers.” Sad!
Sad songs, you say?
I find that the Band’s “It Makes No Difference” starts strong and then weakens … but hearing Rick Danko lean into the line “Now there’s no love / As true as the love / That dies untold” is always touching.
“Acadian Driftwood” is sad in a different kind of way, with Richard Manuel (I think it’s Manuel) singing in French about his homesickness.
The Beach Boys’ “Caroline, No” might have kind of a cheesy teenage aura about it, but regret for the loss of a close connection with someone else is eternal.
Pink Floyd’s “Wish You Were Here” … when David Gilmour’s ragged-sounding voice enters, he sounds like he’s been up all night arguing with somebody who’s now in the process of packing their bags.
John Cale’s “I Keep A Close Watch” is crazy sad, especially in its solo piano version: https://www.youtube.com/watch?v=PEk4zY-6P-k
And finally there’s the Velvet Underground’s “Sad Song,” which is not actually all that sad, but which I like a lot anyway:
Au contraire: According to the noted 20th century philosopher Nick Lowe, “Time Wounds All Heels.”
Jim, a couple of songs you’ve referenced in the past certainly qualify. One is “Maggie’s Dream” by Don Williams. Another is “Good Time Charlie’s Got The Blues” by Danny O’Keefe. I’ll throw in “Rainy Night In Georgia” from Brook Benton. All three of these (especially “Good Time Charlie’s….”) are straightforward, and don’t manipulate or jerk heartstrings like Harry Chapin’s catalog often did. As a result, they pack a wallop like a fastball by Randy Johnson
“Everything I Own” is tough for me to hear ever since my father died and knowing that David Gates wrote it following his own father’s funeral. It’s a great song, but to make it all the way through without tearing up now is well nigh impossible.
Some others not mentioned here:
“Bmma” by Hot Chocolate–This song about a wife’s suicide had its inspiration from the death of co-writer Errol Brown’s mother. The pain in Brown’s vocals near the end accentuated with sharp guitar riffs make this a stark listen.
“Shannon” by Henry Gross-Yeah, it’s about the loss of a dog. Anyone who’s had a pet can relate to this.
And it wasn’t written to be a sad song, but hearing Karen Carpenter sing the opening verses of “Only Yesterday” is a kick in the gut in light of her early demise: “After long enough of being alone/Everyone must face their share of loneliness/In my own time, nobody knew/The pain I was goin’ through/And waitin’ was all my heart could do….”
Scott Paton for the win (i.e. the list that most resembles mine)!
I’d add:
When I Look in Your Eyes-Andy Williams’ version (from Dr Doolittle)
Do You Believe Me Now-Vern Gosdin
Holdin’ On to Yesterday-Ambrosia
I Was Lonely When-Cryan’ Shames
So Lonely-The Hollies
Mandocello- Cheap Trick
(maybe these aren’t all “sad” but treading that fine line between “haunting” and “sad”)
I’m floored every time I hear George sing:
“As you leave you’ll see the nursery
oh, she left me without mercy
Taking nothing but our baby and my heart
Definitely “Shannon” by Henry Gross – he still receives emails from people when they lose their dog. It comforts them. Some of those who thought it was corny have come to love and appreciate it as the years go by and they become battle worn.
Another Abba contender is “Slipping Through My Fingers.” And I’ll have a thing or two to say later this week about Iris DeMent’s “My Life.”
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