The saddest song of all time

Kate & Anna McGarrigle’s “Heart Like a Wheel” came on recently, and once again I was moved to tears.

For me, this is the saddest song of all time.

It’s not just the song, though Anna McGarrigle’s melody and lyrics are finely wrought. It’s also the exquisite production — by Joe Boyd — and the McGarrigle sisters’ heartbreaking vocals. This verse, in particular, reduces me to a puddle:

When harm is done no love can be won
I know this happens frequently
What I can’t understand
Oh please God hold my hand
Is why it should have happened to me

That “Oh please God hold my hand” is devastating. It’s practically parenthetical, almost tossed off. But the singer is completely bereft. I can hear Anna’s heart breaking. All I want to do is hug her like a child.

Other versions of the song — Linda Ronstadt’s is the most famous — may be letter-perfect, but just don’t reach the beautiful depth of the McGarrigles’. I think it’s the willingness of Anna McGarrigle to expose (just enough) her hurt soul — that and the empathy she inspires. I get the same feeling with Dolly Parton’s “Down from Dover,” Sinead O’Connor’s “Nothing Compares 2 U” (perhaps the saddest song to hit No. 1), the Beatles’ “Eleanor Rigby” and the Kinks’ “Young and Innocent Days” — though perhaps that last is more wistful than sad.

Indeed, there are all kinds of fine lines you can draw when it comes to sad songs. Are first-person tales more effective than plainly presented third-person narratives? Is less more when it comes to singing and production styles? Paste and Rolling Stone have whole lists of sad songs and though I agree with many of the selections, some of them just don’t move me. I can’t separate “Last Kiss” — whether J. Frank Wilson and the Cavaliers’ version or Pearl Jam’s — from the whole teen death song genre, which is just morbid. George Jones’ “He Stopped Loving Her Today” has Jones’ brilliant vocal, but the song is undone by Billy Sherrill’s overly weepy production.

And don’t get me started on Bobby Goldsboro’s “Honey.” There’s sad, and then there’s mawkish.

As they say on the Internet, your mileage may vary. All I know is, when I hear something like “Heart Like a Wheel,” I have to pause for breath. It’s powerful stuff.

What are some of your nominations — and why do they move you? Leave them in the comments.



3 thoughts on “The saddest song of all time

  1. “Heart Like a Wheel” is a beautiful song, and a great contrast with the sweet (and sly) playfulness of “The Swimming Song.”

    I nominate Aretha Franklin’s 1985 version of “Sweet Bitter Love” as the saddest song. She first recorded the song as a 24-year old trying to make her mark in music with the help of her father and mentor, the famed gospel performer C.L. Franklin. This version is a lovely, skilled performance, but without emotional understanding, and the arrangement is too fast and too pretty. Fame would wait another year.

    In 1979, C.L. was shot in his home during a robbery. He slipped into a coma from which he never recovered. His health started fading in 1982, and Aretha moved back to Detroit from California. This caused her separation from her second husband, Glynn Turman; the divorce became final in 1984. C.L. passed away that summer.

    In late 1984 and early 1985, Aretha recorded “Who’s Zoomin’ Who?” an album with assured pop tunes, an array of guest stars, and all the slickness you would expect of the era. It was a smash. But Aretha self-produced two tracks with none of the gloss of the hits, the flowing groove of “Integrity,” and her remake of “Sweet Bitter Love.”

    Much as she loved C.L., his philandering had ripped apart Aretha’s childhood home. Aretha’s first husband, Ted White, was notoriously abusive. One senses that all these troubled relationships with men who were supposed to support her fueled the singing of the remake. Van McCoy’s written lyrics are simple, but eloquent, and Aretha fills the spaces with pain, and she roars the second bridge: “My magic dreams have all lost their spell/And where – where I had a little bit of hope, there is….Ah, look at me now!..There is an empty shell.”

    She has to come down from this rage, and she winds down to the conclusion: “Why have you awakened and forsakened a trusting heart like mine?” The music sighs to its end, then Aretha sings something incredible in mid-line: “I love you boy, yes I do.” Had she found someone to comfort her, someone watching this over-powering performance? It’s the only point of light in a devastating recording.

    Here it is:


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