Why do we love sad songs so much? I should probably amend that question to “why do some of us love sad songs so much?” I don’t think everyone does. Just like not everyone loves horror movies or roller coasters. But it’s plain to see that all of these things have legions of fans.
Sorry – I don’t have an answer to my question. I have a vague notion but that’s all it is. It's analogous to our passion for horror films and roller coasters, though not exactly the same. It has to do with catharsis. We all know what life has in story for us. We all know where it ends. One way to deal with that realization is to confront it in bite-sized pieces – a movie or ride perhaps. Or a song.
Music is uniquely suited for this purpose. Music overwhelms our emotions on a visceral level. There are scientific theories about how and why this happens but we all know it intuitively. A melody gets into the blood stream in a way that other thoughts, feelings, ideas … cannot.
20 sad songs to brighten your day
If you can pair that with arresting poetic and narrative flourishes, you have a very powerful tool at your disposal. Music is a Trojan Horse that gets inside you, allowing those words to have maximum impact.
Anyway, that’s my notion.
Today, we’re seeking out twenty of the saddest songs modern popular music has to offer. Of course, this universe is too big to make this a definitive list. I considered narrowing the focus to a specific genre or subject – e.g. “The saddest rock songs about death.”
But I rejected that. It felt too limiting.
So what follows is an eclectic list which spans genre, subject and era. And to keep things a little more interesting, I decided to pair up my choices. So instead of 20 songs, you get ten pairs of songs. They are grouped together by ….
You know what? You’ll see for yourself.
Break-ups
“For No One” by the Beatles (1966) and “A Good Year for the Roses” by various
There is no more fertile topic for a song than love and no more fertile topic for a sad song than the end of a love affair. Choosing the two best is kind of like choosing your two favorite grains of sand on the beach. But I’m comfortable with these.
Paul McCartney’s “For No One” combines his magical sense of melody with simple understated lyrics that capture the heartbreak caused by one half of a couple moving on while the other half stagnates. His final verse is as economical and poignant as you will find ...
“You stay home, she goes out
She says that long ago she knew someone, but now he’s gone
She doesn’t need him”
Plus, there’s that utterly expressive French horn.
Jerry Chesnut wrote “Good Year for the Roses” and George Jones made it famous in 1971. For reasons that will become clear later, I will highlight Elvis Costello’s lovely cover 10 years after that.
Regardless of which you prefer, Chesnut uses the classic device of juxtaposing mundane domestic chores with the utter collapse of a family to heartbreaking effect. Performed by great singers, he wrenches enormous emotion out of a simple line like:
“After three full years of marriage
It’s the first time that you haven’t made the bed.”
Break-ups, part 2
“April Come She Will” by Simon & Garfunkel (1966) and “Simple Twist of Fate” by Bob Dylan (1975)
These songs build on the typical break-up sadness by offering a counterpoint. They do not merely focus on the break-up. They build to it by outlining the rise of the relationship, thus rendering the inevitable fall all the more melancholic.
Paul Simon wrote “April Come She Will” but Art Garfunkel sang lead (one of the few times he did) and it makes a difference. Garfunkel’s sweet tenor was better suited for tender emotion, as he would famously demonstrate on “Bridge Over Troubled Waters.” And he sings the final words with a simple and powerful beauty.
“August, die she must
The autumn winds blow chilly and cold
September I’ll remember
A love once new has now grown old.”
As for Dylan, in typical fashion, he creates a cinematic portrait of a single night that haunts a man’s dreams forever.
“He woke up, the room was bare
He didn’t see her anywhere
Told himself that he didn’t care
Pushed the window open wide…”
Death of a lover
“Eli the Barrow Boy” by the Decemberists (2005) and “Elephant” by Jason Isbell (2013)
Death, as we will see in a moment, is an obvious subject for a sad song. And the death of a lover? The trick here is not getting overly sentimental. This usually requires extreme skill in songwriting, which fortunately, these to writers possess.
Colin Meloy, the Decemberists’ frontman, is a published children’s book author and the simplicity of his approach is on potent display in his story of Eli. His voice floats above a sweet acoustic guitar, singing in both first and third person about a poor boy who follows his lover into death. Despite the obvious pathos, Meloy never goes too far, in part by focusing on the details of his story..
“Below the tamaracks he is crying
Corn cobs and candlewax for the buying
All down the day”
Isbell also builds his song on an acoustic guitar with a few other minor embellishments. His lover is dying and they are trying to go about their lives as best they can. The title is the central metaphor – trying to avoid the elephant in the room.
“When she was drunk she made cancer jokes
Made up her own doctor’s notes
Surrounded by her family, I saw she was dying alone”
Death
“Jackie” by James McMurtry (2021) and “Middle of the Heart” by Adeem the Artist (2022)
This is such a vast territory for sad songs. I decided to go with two very recent songs that may not be as well known as, say, “Eleanor Rigby.”
McMurtry is right near the top of greatest American songwriters working today. Each of his numbers tells a completely inhabited story and none are as heartbreaking as this one about woman who drives a truck so that she can indulge her true passion of raising horses. I wish I could write one lyric as evocative as…
“She jackknifed on black ice with an oversized load
There’s a white cross in the bar ditch where she went off the road.”
Adeem’s outstanding album White Trash Revelry runs the emotional gamut from the raucous “Going to Hell” to the emotionally devastating “Middle of the Heart” which tells the story of a sweet and simple country boy who is trained to be a killer as a member of his country’s military forces.
“Nights get longer
Days get hard
I learned to put a bullet through the middle of a heart.”
Spritual stagnation
“Fast Car” by Tracy Chapman (1988) and “The Girl in the Picture” by Ashley McBryde and Pillbox Patti (2022)
I don’t mean to suggest that men can’t suffer from spiritual stagnation but I also realize that I have now written about eight songs and all eight were written by men. At the risk of sounding …. gasp … woke, I think that may indicate a bias in my musical preferences.
I actually initially had a devastatingly sad song on this topic – “The Ballad of Lucy Jordan” – which was written by a man but made famous by a female singer back in 1979. But I chose something else because, well, you’ll see…
“Fast Car” was always going to be on this list. It is among the most poignant, gut-wrenching songs I know, and it does not rely on romantic failure or death or disease or specific tragedy of any kind. It simply rips its story from everyday life and Chapman captures that unfulfilled yearning as well as anyone ever has in a song.
“You got a fast car
But is it fast enough so we can fly away?
We gotta make a decision
Leave tonight or live and die this way.”
Ashley McBryde, along with multiple writing partners, created an entire world in her glorious 2022 album Ashley McBryde Presents: Lindeville. The third song (and fourth track) tells the story of an anonymous beauty who is captured in a prize-winning photograph, which is the highest she will ever fly. McBryde uses a brilliant writing technique in a bridge toward the end of the song, for the first time calling her subject by her name.
“Shouldn’t be a prize
For catching the last smile of a girl named Caroline.”
Unequal gender politics
“Caroline Says II” by Lou Reed (1973) and “Unwed Fathers” by John Prine (1989)
Back to the boys writing about the girls. There is an inherent mea culpa coming from both Reed and Prine about the way men take advantage of the power they are gifted by society in both physical and emotional ways.
Reed wrote multiple songs on the “… Says” model but none were as devastating as this account from his austere Berlin album. It is a story of a woman trapped in an abusive relationship with no real way out, except perhaps going to Alaska, which as you might guess, is a metaphor.
“Caroline says
As she gets up off the floor
You can hit me all you want to
But I don’t love you anymore”
Prine, a far more sympathetic soul than Reed, expresses an almost unspeakable tenderness in his portrait of a teenage girl who must suffer the consequences of sexual experimenting, while her partner runs free.
“In a cold and gray town
A nurse says lay down
This ain’t no playground
And this ain’t home.”
The bottle
“Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” by Tom Waits (1976) and “Here Comes a Regular” by the Replacements (1985)
Singing about being drunk is even more fraught with pitfalls than writing about heartbreak and death. It takes a very sophisticated writer to avoid mawkishness.
Part of Waits’ genius as a songwriter is how he can filter stories without losing any immediacy. Here, his heartbreak is exacerbated by being lost in a strange land. Thus he becomes an outsider in multiple ways. And he chooses alcohol to medicate himself, thus adding an additional layer of loneliness. SPOILER – his use of one particular musical motif will crop up in another song before we are done.
“And it’s a battered old suitcase to a hotel someplace
And a wound that will never heal
No Prima donna, the perfume is on
An old shirt that is stained with blood and whiskey.”
The Replacements were nearing the end by 1985 and a large part of it was the result of frontman Paul Westerberg’s desire to write songs beyond the loud confines of drunken punk. For the final track of Tim, he essentially performed a solo acoustic ballad about life in a bar … kind of the heartbreaking flipside of Cheers.
“Well a person can work up a mean, mean thirst
After a hard day of nothing much at all.”
Kids
“Luka” by Suzanne Vega (1987) and “Let’s Stay Together for the Kids” by Blink 182 (2001)
You may be noticing a recurring theme here. Certain subjects – romance, mortality, addiction – are prime territory for sad songs but unless they are handled properly, the songs will come off as overbearing. The same applies to writing about children and the hardships they may suffer.
Vega, who if I remember correctly, said she had her eyes opened to more nuanced subject matter after hearing Lou Reed’s Berlin, approaches “Luka” from an angle. Despite the fact that the song is clearly about child abuse, a lot of listeners missed that on first listen.
It has a spry musical attack that is nonetheless vaguely foreboding and a superficially quirky central character who is nonetheless chilling. It is only when you really listen that you get the sense of dread that is layered into the story.
“They only hit until you cry
And after that you don’t ask why
You just don’t argue anymore”
Despite the very poignant “Adam’s Song” from 1999’s Enema of the State and several other deceptively incisive explorations of emotional isolation, when “Let’s Stay Together for the Kids” came out, it still shocked listeners that Blink could produce something so emotionally mature.
After all, it was from an album called Take Off Your Pants and Jacket. Tom DeLonge writes about a troubled married couple from the POV of a questioning child and thinks about what kind of damage is done in this all-too-commonplace situation.
“I’m ripe with things to say
The words rot and fall away
What stupid poem could fix this home?
I’d read it every day.”
Country
“He Stopped Loving Her Today” by George Jones (1980) and “Whiskey Lullaby” by Brad Paisley and Alison Krauss (2004)
I’ve avoided broad genre associations up ‘til now but I am making an exception here. Country music has probably been responsible for more sad songs than any other genre. Obviously, another long list could be made up of the saddest country songs, but I offer these two as standout representatives of the genre.
Jones was also responsible for an earlier song on this list – “A Good Year for the Roses,” which is one of the reasons I mentioned the Elvis Costello version. I knew George would be showing up later. He was always known for wrenching emotion out of every song he sang and when he got a particularly powerful composition to attack, the results were extraordinary.
That’s what he got with this Bobby Braddock-Curly Putnam number. And he also had the support of producer Billy Sherrill who helped him through some difficult personal issue to create this masterpiece. It is basically another heartbreak song but the overwhelming potency of the conception is slowly revealed.
The singer did in fact lose his love. But he never stopped loving her. Right up until the day he died.
“He kept some letters by his bed
Dated nineteen sixty-two
He had underlined in red
Every single ‘I love you.’”
“Whiskey Lullaby” is just as sad as it gets. It’s there in the music and there in the lyric and in the resolution. It is poetic, but it is not subtle or full of hidden meaning. It combines much of what we have been discussing – heartbreak, alcohol, death. Krauss’s second verse really puts this over the top by depicting how one tragedy causes ripples that live on.
“The rumors flew
But nobody knew how much she blamed herself.”
War
“The Band Played Waltzing Matilda” by the Pogues (1985) and “Al Bowlly’s in Heaven” by Richard Thompson (1986)
This is where I got the idea for pairing songs. These two songs, from British Isle performers released a year apart in the mid-1980s, both recalled the trauma of a long-past war. And both use musical references to tell their stories.
Eric Bogle wrote “The Band Played Waltzing Matilda” and Shane McGowan gave it his typical gloriously ramshackle reading (much like Tom Waits, who had used the “Waltzing Matilda” motif in “Tom Traubert’s Blues” a decade before). Youthful vigor snuffed out by the carnage of war.
“How well I remember that terrible day
When the blood stained the sand and the water
And how in that hell that they called Sulva Bay
We were butchered like lambs at the slaughter.”
Thompson covers very similar territory, though he is more focused on what life has become for an invalid struggling in the long years after the war. Al Bowlly was a famed music hall singer who the narrator recalls as a representative of those happier days when he had a future.
“I gave my youth to king and country
But what’s my country done for me
But sentence me to misery?”
So check out these songs when you want to feel the tears, then switch back to Olivia Dean or Olivia Rodrigo -- choose whichever Olivia you like -- to add some balance back into your life. It'll be an emotional roller coaster, but at least it won't be a real one.
Add us as a preferred source on Google