Blue Monday - The Saddest Songs Ever
Published on 20 January 2025
Blue Monday definition: “A Monday in January, typically the third Monday of the month, that is characterized as the most depressing day of the year”.
Why are sad songs so powerful? Do you listen to sad songs when you feel down? Do they make you somehow feel better? I often wonder why that is, and I suppose it may be the recognition of your emotions by the artist, and a mirroring of your situation.
Maybe it’s something else? Maybe sadness just has a beauty to it, and in our lives we tend to try and accumulate as much beauty as possible.
Who knows? What we all do know is a sad song when we hear one. Whether that sadness is instant and obvious or creeps up later when you’ve heard the tune a few times and the lyrics are sinking in, there’s nothing like a sad song to make us stop, reflect, and feel something.
Today, I’ve gathered together some of the saddest songs ever recorded in order to help you gracefully cry your way through Blue Monday, which just happens to be today, January 20th! Sad songs are always useful to have around though, so whenever you read this, I hope you enjoy wallowing in all of this beautiful misery!
The Sad Songs at a Glance
Tears in Heaven - Eric Clapton
I Wish That I Was Sober - Frightened Rabbit
Coat of Many Colours - Dolly Parton
Caroline Says Part II - Lou Reed
Flowers and You - Touche Amore
Georgia Lee - Tom Waits
Tom Waits isn’t shy of a few tearjerkers in his inestimable back catalogue, but this one hits particularly hard. A local 12 year old girl - the titular Georgia Lee Moses - was murdered in real life, whilst out wandering about in small town California near to where the Waits family lives. The murder wasn’t properly reported, and hardly covered by the local news, far less national outlets. Tom’s own daughter, who was watching a news report of the still unsolved murder, asked why even the town didn’t seem to care about it, and it broke his heart. The song - which avoids overt moralising to instead paint a stark picture - was his response.
Asked about Georgia Lee, Waits said this: “It made sense that the song belonged to someone who could use it to help other children. It felt like it wasn’t mine anymore. It belonged to her, and it belonged to the people out there trying to do good in the world.”
Dancing Queen - ABBA
How can this disco classic be anything other than joy-filled and euphoric? Well, the key here is to pay attention to the lyrics. The subject of the song - the young, carefree, beautiful ‘dancing queen’ - is not the person singing the song. It’s somebody else, sitting on the sidelines and gazing over at the person they wished they were, but know they are not. It’s all a vicarious exchange from a lonely soul, someone whom the dancing queen might not even know - or notice - in the nightclub, surely the saddest place in the world to be alone.
Fast Car - Tracy Chapman
This one was pointed out to me recently and oh my goodness is this a tragic song! I must’ve heard this hundreds of times and never taken in the lyrics, which talks of the vicious cycle of life: poverty, alcoholism, broken homes, trying to make dreams come true…it’s all very relatable and not what I expected from my casual listening!
The narrator seems to be trying to support their partner or family, but their sacrifices aren’t being met by life. Here’s a sample lyric, which seems to hint that the narrator has finally had enough if it by the end:
“You got a fast car/ We go cruisin', entertain ourselves/ You still ain't got a job/ Now I work in the market as a checkout girl/ I know things'll get better/ You'll find work and I'll get promoted/ And we'll move out of the shelter/ Buy a bigger house and live in the suburbs. You got a fast car/ I got a job that pays all our bills/ You stay out drinkin' late at the bar/ See more of your friends than you do of your kids/ I'd always hoped for better/ Thought maybe together, you and me'd find it/ I got no plans, I ain't goin' nowhere/ So take your fast car and keep on drivin'.”
Tears in Heaven - Eric Clapton
It doesn’t get sadder than the loss of a child. Blues megastar Eric Clapton lost his infant son when he fell from a window, and his artistic response was this gentle, tender acoustic ballad.
“Will you know my name/ When I see You in Heaven?” must be one of the saddest first lyrics in history, particularly when sung from a grieving father to his departed son.
I Wish That I Was Sober - Frightened Rabbit
This song had a dark power to it from the beginning, but in light of what ultimately happened to Frightened Rabbit vocalist Scott Hutchison, it becomes an almost unbearable listen.
“Fall prey to the blizzard head / Wrapped my hand around the glass again / We all thought that I might change as I got older / Fell down and nothing bled / Wrapped in cotton alcohol again”
Scott was a regular customer to our Glasgow store, and those of us who worked there at the time all remember his big smile and gentle humour very fondly. Whilst art and life can certainly be serrated, it’s worth remembering that we never really know the inner struggles that people around us endure.
Coat of Many Colours - Dolly Parton
Bullying is something that touches too many people, and Dolly Parton’s lyric here is about a home made - and deeply cherished coat - that the wearer gets laughed at for wearing to school. Dolly makes a point of saying how much love was poured into making the coat, but that her tormentors only see it as an example of her poorness.
However! It’s also a quietly triumphant song (I’m stretching a bit here, it’s actually super sad) because Dolly’s character is defiant, telling her that regardless of how rich she could be, that coat with all of its built-in love would be the one she’d wear.
Caroline Says Part II - Lou Reed
Lou Reed’s Berlin record is sneaky and deceptive. Why? Because it’s a melodic and beautiful sounding record, with some of the darkest and saddest lyrics ever collected in one album. It’ll trick you into liking it despite how bleak and hopeless it is.
Why so? Well, the protagonist - Caroline - is abused by her husband, used by her friends, becomes an addict, gets her kids taken away (sample lyric: “They’re taking her children away, because they say she is not a good mother”) and ultimately reaches oblivion.
That would be bad enough, but it’s the ups and downs of her story, told mainly from the points of view of others, that gives this album its stark power.
Caroline Says is a song of two parts, and part two is as tough as it gets:
“Caroline says / as she gets up from the floor / You can hit me all you want to / but I don't love you anymore / Caroline says / while biting her lip / Life is meant to be more than this / and this is a bum trip / But she's not afraid to die / all her friends call her "Alaska" / When she takes speed, they laugh and ask her / What is in her mind?
Elephant - Jason Isbell
Former Drive By Trucker Jason Isbell doesn’t shy away from difficult subject matter, but Elephant is still one that stands out. It tells of two friends who’ve both lived a little, shall we say. They are out enjoying an evening at the bar and just trying hard to avoid the fact that one of them is dying of cancer. That’s the elephant in the room, and each others’ past life holds heavy in their interactions.
“She said, "Andy, you crack me up" / Seagrams in a coffee cup / Sharecropper eyes and her hair almost all gone / When she was drunk she made cancer jokes / Made up her own doctor's notes /Surrounded by her family, I saw that she was dying alone”
Isbell talks about the song’s genesis: “I’ve spent a lot of time at little bars in Alabama, getting to know a lot of people who’d eventually disappear. It’s kinda like that scene in Rent, when everyone starts vanishing. It was that way in this particular bar. I was dating the bartender, who was young, real sweet and kind hearted, and I said, “You know, these people aren’t gonna be around forever. You’re gonna get connected to these old drunks, and they’re just gonna vanish. Every few months, another one’s gonna be gone.” The song just came from that place – from having that connection with someone whose ship is going down, and allowing the relationship to mature in spite of that. Two people are sitting on barstools for a long period of time, and one person gets sick, and the other rises to the occasion.”
Flowers and You - Touche Amore
This is another tune about coping with the illness of a loved one, in this case the singer’s mother. The lyrics veer away from art towards a plain confessional, perhaps in the hopes of some degree of catharsis. Not knowing what to do or say is such a universal and deeply feared thing, and it’s addressed very honestly here:
“I apologize for the grief / When you'd refuse to eat / I didn't know / Just what to say / While watching you / Wither away / I'm homesick / And living in the past / Seemingly unfazed and strong if anyone asks / I'm keeping up appearances with white lies / With a levee set / For my heavy eyes”
The Happiest Song in the World
Oh my, we need some cheering up now, don’t we? That was a tough trawl there, through some of the saddest songs ever penned. What I’d like to finish up on is a blast of unadulterated happiness, silliness and irony-free fun.
Let’s end this blog with Cyndi Lauper’s instant feel-good anthem Girls Just Wanna Have Fun. Make this the song you have stuck in your head after you finish this blog! And remember, Blue Monday is only one day: things will seem much better tomorrow!
