Plus, the Different Types of Heartbreak Songs, How Soul Music Perfected the Horn, and Defining “All Time”
But first: the spotify playlist that accompanies this list
Looking back on it now, I spent most of my teen years in a sleep deprived stupor due to a vicious cycle of:
- anxiety about going to school tomorrow
- means not falling asleep
- means I’m overtired all day
- which makes my emotions even more unbalanced than the already imbalanced teenage psyche
- which increases my anxiety about going to school tomorrow
- which, as Brian McKnight once said, means I “start again at (step) 1”
The upside to this may have been that I spent a lot of time leaning into my sadness, mostly through listening to sad music.
It turns out a lot of people do this for exactly 4 reasons:
Within all samples, the top five reasons include To listen to music privately (#2, #1 and #1 for S1, S2 and S3 samples, respectively), closely followed by beauty of the music (#1, #2, #3), and to get comfort (#3, #4, and #5 reason across samples), and to reminisce (#5, #2, #5) – PLOS ONE
Via my healthy “get sad so you can sleep” habits, I developed an appreciation for the varied qualities of sad songs.
There are your White Guy Alone in the Woods with a Guitar Mostly Because He Wants To Be stuff like “Song for Woody” by Dylan, or Nathaniel Rateliff’s earlier recordings.
Then there’s the songs from the Suicidal Rainy West Coast White Guy thing that Elliott Smith and Kurt Cobain both painfully lived out.
And then, there are of course many…
Different Types of Heartbreak Songs
The “I’m Not Missing You But Really I Am” type
The “I Would Do Anything To Get You Back” type
The “I Will Never Be With You” type
The “I’m Alone With My Lonliness” type
The “I’m Still Not Over You But I Am Comfortable With Sharing That Information” type
The dangerous, “Contemplating Who You’re With Now” type
And maybe the most annoying, “It Was My Fault That I Dumped You” type
I say all this to say, there are many ways to be sad and many types of sad music, but for my money, none are better than Soul music.
The Horn
Whatever type of sad music you find the most sad, I find it unarguable that soul music has perfected the horn. And I don’t mean, “soul music does horn composition better than any other 20th/21st Century Genre”.
No. I’m saying classical composers didn’t understand horns the way soul musicians of the mid-20th century did. Horn parts in Soul music are the physical sound of melancholy.
They can punch, and they can simmer. They swell and then they bounce. They’re brassy with excitement and somber in their wailing.
Horns pull your heart strings like no strings can. Give me an old analog organ and a trumpet part and you can just take all my money.
Against that backdrop, the perfection of the horn, come most of the best sad songs of all time. Since most songs need someone to sing them, let’s look at the criteria of what makes someone a contender for:
The Saddest Voices of All-Time* Criteria
- By “All Time” I mean the modern, post-Rock n’ Roll era that most people mean when they say “All Time”. Sorry Billie Holiday.
- A “Saddest Voice of All Time” voice not only conveys sadness well through their voice, but they also, importantly, tend to sing sad songs. Aretha Franklin is unquestionable, but I would argue most of her catalog is upbeat. When I think “sad music” I don’t think Aretha Franklin.
- Aka 1b. Not the Blues. I know modern pop culture. I do not know pre-War blues music. The depth of pain and sadness the blues was invented to express, and did successfully for generations, is something I can only imagine a few singers on this list capable of expressing. Blues is why we have the bounce of Rock n’ Roll and the sadness in Soul but I can’t do those artists justice here.
The Saddest Voices of All-Time*
#14 John Lennon
John Lennon once wrote, “The only thing you ever done was Yesterday” during his feud with McCartney post-breakup.
I find it telling that John pointed out, what seems to me, like the only sad song Paul wrote during the Beatles time together.
Yes, they “co-wrote” their songs, but we know whoever wrote it also sang it, and Lennon’s voice and writing style lead to the heavier songs in the Beatles catalog.
#13 Adele
People underestimate how hard it is to not only sing on key, but to sing with emotion.
Kesha without auto-tune is notoriously off-pitch, but with auto-tune they keep using her because she brings attitude. That’s how much “attitude” (read:emotion) is valued.
Adele can sing with emotion, to say the least.
#12 Justin Vernon
Italo Calvino once wrote, “Meloncholy is sadness that has taken on lightness”.
Justin Vernon’s voice is meloncholy that has taken a residency in a Wisconsin cabin watching the snow fall as the fire crackles and you sip tea and/or scotch.
#11 Van Morrison
Van Morrison is the most soulful white guy ever. It makes sense that he’s Irish.
Astral Weeks (full disclosure) is my favorite album of all-time, in the way where it feels like an album is you.
Van Morrison is able to pull emotion out of a word through its teeth, making a walk in a field feel like your last bad break up is happening all over again.
Speaking of white guys, yes, that’s what this list has been so far…only because they’re not at the top of it.
#10 Elliott Smith
Sometimes I can’t understand what part of Elliott’s Smith music was better, his voice or his writing.
His voice is so sad it borders on suicidal. It’s the type of sadness you never want to leave…in the unhealthiest of ways.
That said, I’ve catharsis-ized through many a Terrible Tuesday, often catching myself saying, “that’s it, I’m only listening to Elliott Smith for the rest of the day”.
#9 Gladys Knight
Gladys Knight’s sadness always made me feel better. That sounds bad, but hear me out.
She sang songs about
- How she’d “rather live in his world, than be without him in mine”
- How her love was like diamond, but treated like glass and how “you beg her to love you, but me you don’t ask”
- how she’s not the “woman you go home to” but the one you leave behind.
Damn, I would think, if a woman like Gladys Knight feels like I did as a 15 year old, pimply, depressed white boy, then there was hope for me yet.
Like many on this list after her, she not only had a beautiful and clean voice, she knew exactly how to dirty it up when the emotion of the song called for it.
#8 Marvin Gaye
While Marvin Gaye might, arguably, be the best singer on this list, his overall body of work isn’t that sad. That said, this trinity will knock you on the floor: “Inner City Blues (Make Me Wanna Holler“, “Trouble Man” and of course, the vocals on “Mercy, Mercy Me“.
He would be higher on the list if he sang more sad songs, but this acapella performance, which puts to the side the pop-perfect production that Motown strived for, gives in an insight into just how painful his voice actually sounded underneath all that polished instrumentation and hook-centric lyricism.
#7 Irma Thomas
Let’s look at how depressing Irma Thomas’ song titles are, “Wish Someone Would Care”, “Cry On“, “Time Is On My Side“. Ok the last one isn’t really sad so much as it is a lie.
Not only were her songs sad, she could add that scratchiness in her throat when she hits an emotional, “yea” like she does at the 1:00 mark of the above song. She could then lull you into thinking you were safe with her smooth approach to the verse, before turning it up again at the next chorus. The combination is devastating.
#6 Ted Hawkins
For a time, Ted Hawkins was a grifting, homeless, street musician. His voice sounds like it. His story is one of a street legend who never got his Rodriguez moment in the sun.
His voice is even more powerful than his story, as it should be with musicians. Every word is raw, every word cracks, every word sounds like it hurts.
“Strange Conversation” haunts me to this day. The acoustic version from Final Tour is preferable to the recorded version if you can find it, it has no electric guitar at the chorus to pull you out of the sadness of Ted’s voice.
#5 Otis Redding
No sad song list is complete without Otis. You could argue I am underrating him here at #5. I would agree except to say that those ahead of him on this list are even further underrated – if it’s possible to underrate the greatest soul singers of all-time.
Otis Redding could so completely jump from simmering and smooth to punchy and painful you would think his heart was constantly broken.
There’s a lot of great Otis Redding songs, but i’m not sure any of them are as heart breaking, nor show off the range of his heartbreaking abilities as, “I’ve Been Loving You Too Long”. This is a song where our protagonist knows he’s in too deep, and just as equally, knows that he can’t stop now.
About seeing Mr. Redding perform, from The New Yorker
White audiences of the time had never seen anything like it. The effect was so powerful that Bob Weir, of the Grateful Dead, said, of Redding’s performance at the Monterey Pop Festival, “I was pretty sure I’d seen God onstage.”
#4 David Ruffin
I think this is a voice that is largely overlooked when it comes to those popular conversations we all have at the local pub about which songs make us cry real hard. You know, those very, very common conversations we all have with our guy friends about crying.
But just listen to these titles, “My Whole World Ended (The Moment You Left Me)“, “Statue of a Fool“, “Walk Away From Love“, “I’ve Lost Everything I Ever Loved“, “The Double Cross”.
And his voice lives up to the titles completely; pouring real feeling into songs whose lyrics could’ve easily slipped into saccharine with a lesser singer. David was thought of as a generational talent and voice, something beyond just sad.
#3 Nina Simone
Of all the singers on this list, I feel especially unqualified to write about Nina Simone. Her shadow is large and long. Her stoicism – onstage right next to her expressive, generational piano talent – is intimidating to say the least.
Her sadness is often an angry, righteous sadness. See: “Mississipi Goddamn“, or her ubiquitous “Feeling Good” which leaves the listener with the uneasy feeling that the singer might not actually feel as good as her lyrics imply.
But she could also sink into herself, spouting profound, and profoundly painful, one-liners with eviscerating effect: “Stay away from me everybody, cos I’m in my sin“
Her soul is one tied to the blood-stained roots of the American South, tied to Ella Fitzgerald and trees filled with black body parts, tied to her jazz standard roots and her civil rights coming of age. Her voice is the bitter, burning tragedy of American history, while it transcends that tragedy at the same time.
#2 Etta James
While we might not think of Etta James as having the same catalog as the largest of soul icons, I think the beauty of this list is to focus on the voice.
Where Nina Simone was fierce and forceful, where David Ruffin was yelling and pleading, where Otis was powerfully heartbreaking, Etta had the ability to convey the moment a lover loses their hope of ever being loved again. Even though she’s singing, you believe every syllable when she sings, “all I could do was cry”.
The creak in Etta’s voice when she sings “it was over” on the opening line of “I’d Rather Go Blind” is what this entire list is talking about.
#1 Ray Charles
I’m not sure we as a culture understand how important Ray Charles is.
I don’t know that there was a more pivotal artist in the early days of R&B, the early days of Rock ‘n Roll, the early days of what has become the continuum of “pop culture” post World War 2.
But for the purposes of this list, his voice: I don’t think there is a sadder vocal performance beginning in the middle 20th century until present day, than “Hard Times” as sung by Ray Charles.
If you cut out the parts from 1:45 (“I had a woman lord”) to the end of the song and turned it into a picture, you could hang it above every dive bar in America and sales would double at gut-wrenching, heart aching sight of it.
I hope, now that he’s gone, there are no more hard times for Ray Charles because he sure made them sound beautifully, unbearably painful.