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Twenty Sad Songs to Wallow In

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An elite culture snob not keeping his stupid opinions in his pocket

Why am I forcing this on you?

Hi there first article or list or “listicle” however the yoofs want to say it. I stumbled on Nalina Marquez’ list of sad songs, while trying to find proof that someone else finds “5 Years Time” by Noah and The Whale as sad as I did and so gave Nalina’s list a read and a listen. Although some of her choices are dope (almost anything Regina Spektor does I will flex with) a lot of it came off as a bit, obvious and if you’ll allow me to be obnoxious a bit normie. Also, was not a lover of the list being an odd number so this is not a response but instead an alternative for people that maybe want a bit more variety, so because rules control the fun here they are.
1. No more than one song per artist
2. Big believer in the authorial intent being in effect canon, so no “Into My Arms” by Nick Cave because according to the great Gothic man himself it’s a happy song
3. We’ll keep it a tight twenty (probably)

Okay so let’s cause an argument and pretend that taste is subjective. Why anyone would listen to sad songs will vary from person to person, personally I use them to reflect on experiences which were sad for me but it’s the realisation that that sadness only came about because at one point you were really happy. This in more nihilistic terms is explained well by our best sad boy Sartre in La Nausea where he describes sadness and misery having no end or depth, happiness and joy plateaus but sadness, sadness will never let you down by how strong it can be. I personally am just more attracted to loss or defeat than more uplifting emotions and themes so I get a little kick out of seeing that expressed through music.

Look at this existential dork making me seem smorter

Look at this existential dork making me seem smorter


Make Love

Daft Punk

Human After All

Back Together


There's Something Going On

Aloha Oe



If I Was Your Girlfriend


Sign O' The Times

Dead Head Blues

Lightspeed Champion

Life is Sweet! Nice to Meet You.

I Love You All


Frank OST

I'm Not Gonna Miss You

Glen Campbell

I'm Not Gonna Miss You OST

I Let Love In

Nick Cave and The Bad Seeds

Let Love In

The Only Thing Worth Fighting For

Lera Lynn

True Detective Season 2 OST

Drive Darling


Mutual Friends

Waiting In Vain

Bob Marley and The Wailers



Shakespear's Sister

Hormonally Yours

In Love With You

The Paradise


Comfortably Numb

Pink Floyd

The Wall

A Case Of You

Joni Mitchell


The River

Bruce Springsteen

The River



Dear Tommy (TBC)



Cure For Pain

You're The One

Kate Bush

Red Shoes

In The Wee Small Hours

Frank Sinatra

In The Wee Small Hours

So as the keen eyed reader will have seen there is no representation for classic rock or rap and that is one hundred percent my failing, if I stretched it out to thirty then there would be a reshuffle and definitely an inclusion of The Stones and something by Aesop Rock but alas I didn’t and I won’t so deal with it.

Spider-Man you rogue

Spider-Man you rogue

#1. “Make Love” by Daft Punk
Album: Human After All

So straight up confession I also consider this the best song ever made. Now no I’m not grotesquely stupid hear me out. “Make Love” has always sounded so incredibly sad to me because of the simplicity of it. It’s just two words repeated with some minor changes in iteration. The tune is very simple: a pretty easy piano piece and repetitive drum. But it’s the context of it that makes it so sad, Human After All is roughly about fear and in the film Electroma it shows two robots trying to become humans with the narrative explained by music. But “Make Love” sounds like somebody pleading to the listener to just do this one thing and it always gets me, this sad, begging figure asking us all to do one simple, horrible and terrifying thing to give ourselves completely to love.

#2. “Back Together” by Babybird
Album: There’s Something Going On

What do you mean you’ve never heard of Babybird? Just listen to this, it’s about missing someone so much that you’re driven to the depths of desperation and looking to say anything to that person to make them come back to you. It is not an in depth look at a relationship because when you are in love you can never adequately express it and Stephen Jones (Babybird) knows this and lets us wallow with him in never getting that person we love back.

#3. “Aloha Oe” by Lili’uokalani
Album: Doesn’t have one it’s a sad folk song you animals

“Aloha Oe” was written by Hawaii’s last queen Lili’uokalani by some sources as possibly a farewell song to the American Colonel James Harbottle Boyd who she may or may not have had a romantic relationship with. But it has also become a cultural symbol for Hawaii and Lili’uokalani as a farewell song to the sovereignty of Hawaii as it was annexed and eventually absorbed into the United States. This is not really the place to get into the politics of Hawaiians basically having to transform themselves into tourist attractions to support the state but it is a great piece of music of a native sovereign realising that her country is in effect ending and giving it a farewell as it will lose that identity and be forced to take a new one. It’s also in Lilo and Stitch and a complete tearjerker.

#4. “If I Was Your Girlfriend” by Prince
Album: Sign O’ The Times

Arguably appearing on Prince’s best album is what I consider another killer. See Prince was the greatest musician of all time because of how eclectic he was and how willing he was to embrace the negative parts of himself, including the possessive and jealous nature that he had. It’s also a pretty out there examination of relationships and Prince’s questioning of gender. Because as a very handsome man I have felt jealous of girlfriends closeness to their literal friends and how sometimes it can seem more intimate than what we have. Of course Prince being Prince and being a man (what a man) it inevitably does become jealousy where he sees platonic female relationships as competitive and reaches an almost manic level of insisting that he would be the best girlfriend his lover could ask for. It’s this realization that this possessiveness is harmful as the song comes off as a desperate need to be wanted.

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#5. “Deadhead Blues” by Lightspeed Champion
Album: Life is Sweet! Nice to Meet You.

I actually fell out the loop when it came to Dev’s output until the Red Scare girls started dunking on him again. But I caught him way back when I was a teenager and this one is actually pretty simple in how it conveys missing an ex-lover. It’s also relatable when even when you try to remain friends with your ex and they speak of a new partner it will always hurt if you still hold onto them. Big Mood for everyone at some point in their life. There’s also a neat little version of it in French called “Tete Morte” which gives you double pretension points.

#6. I Love You All by Soronfrbs
Album: Frank OST

Just go watch Frank.

#7. “I’m Not Gonna Miss You” by Glen Campbell
Album: Glen Campbell I’ll Be Me OST

Look at that, two soundtracks in a row. I’m a complete hack. So this is just outside of lyrics a tearjerker. It’s a farewell/love song to Campbell’s wife explaining to her how his Alzheimer’s is going to be worse for her than it is for him. He’s going to forget everything about their time together, everything about his children and it won’t hurt him. I think that’s something we sometimes wish for, being able to forget those we love. The pain of happy memories is extreme but the reality of that wish is heart-breaking and you can hear it in Glen’s voice that he knows this will happen and it’s going to hurt them. And there’s nothing he can do to stop that. Give the doc a watch and also check out Still Alice.

#8. “I Let Love In” by Nick Cave and the Bad Seeds
Album: Let Love In

Nick Cave is easily my favourite Gothic dark man. It would be easy to have picked something from the Skeleton Tree which deals with Cave’s grief over the loss of his son which is documented in One More Time with Feeling - a film which although great I really wish did not exist. “I Let Love In” is a brilliantly haunting song from the album of the same name and is not about any particular relationship or event but more the emotion of love itself and all the consequences you have to accept by letting it in. As usual with Nick this isn’t a light thing, it’s all about despair and castration, insanity and being bound, which accurately sums up the emotion really.

#9. “The Only Thing Worth Fighting” For by Lera Lynn
Album: True Detective: Music From the HBO Series Soundtrack

Another soundtrack!!! Yeah I wouldn’t blame you for clicking away either, complete fraud me. But this is such an incredible gem of a song; talking about a relationship and how when you’re in the throes of someone you love and you see them pulling away you’ll do everything to convince them it’s worth having. Even if it’s not good for either of you to keep on. That sometimes we have a relationship just for the sake of it and that will inevitably hurt someone. It also scores the trailer to easily the most misunderstood second season in modern “prestige tv” in years

#10. “Drive Darling” by BOY
Album: Mutual Friends

What do you mean you have never heard of BOY? Well I won’t do your work for you, go listen to BOY next you’ll be saying you’ve never heard of HEALTH. But why “Drive Darling” is here is a swerve on the themes so far which has been suitably Goth, all regret and tragedy and pain and that good stuff. “Drive Darling” is more a goodbye song to a relationship where both of you are moving on with life but will always cherish the time together. Melancholy gets thrown around a lot on these lists and usually isn’t used properly but “Drive Darling” is actually melancholic, it’s a sadness you can be thankful for, a sadness that you should look forward to. Also, I wrote drive as driev like eight times so that alone gets it a spot.

#11. “Waiting in Vain” by Bob Marley
Album: Exodus

I’m not a particularly huge fan of reggae or Bob Marley in general, but “Waiting in Vain” is such a sweetly sad song where Bob is in love with someone who does not really have the time of day for him but: “The waiting is fine” This develops from unrequited love to Bob talking about his own self-respect for his feelings where he does not want to wait forever and does not want to be treated like this but at the same time that love is worth the wait. I think this is a sad song because there is no shame in loving someone and understanding they don’t feel the same in fact it’s kind of beautiful but the song does point out that it’s harmful with all the time you’re waiting for love you’re missing out on it.

#12. “Stay” by Shakespear’s Sister
Album: Hormonally Yours

What do you mean you’ve never heard of Shakespear’s Sister? Load of normies you lot. Right well you can read about them yourself. Stay is actually a bit of an anomaly for the duo as Detroit takes the lead on the vocals where Fahey provides backing and it’s a pretty clear cut track on a lover dying and the other begging them not to go. The video is maybe a bit too early 90’s for me but gives the song an actual storyline but even without it you’ll get caught up in the frantic begging in the song asking her lover to not leave her behind.

#13. “In Love With You” by The Paradise
Album: Isn’t on one, it’s just a 12’ single but it’s easy enough to find

What do you mean you’ve never heard of The Paradise? Okay this one is a bit obscure but it has had attention before. Shamefully, I heard of this through a Vice article years ago, I say shamefully because dunking on Vice was a hobby of mine and really loving them when they killed it. I’ll post that article here but “In Love with You” is a complete banger. A sad banger but still a banger. A dance track that’s oddly hypnotic a bit like “Make Love” (weird how brilliant French electronic artists are at making sad dance). The song reminds you of the time you said that stupid sentence to someone and how many times you maybe shouldn’t have. Reminds you of all the times someone said it to you and you didn’t feel the same. Reminds you just how great that feeling is.

#14. “Comfortably Numb” by Pink Floyd
Album: The Wall

Bit of a departure here because if you haven’t heard of Pink Floyd we can’t be friends and honestly who has never heard of Pink Floyd?

See these old dames?  They're  laughing at you not knowing Pink Floyd (got this by typing into the Goog: "laughing at someone crying" kinda dark

See these old dames? They're laughing at you not knowing Pink Floyd (got this by typing into the Goog: "laughing at someone crying" kinda dark

Also this one isn’t about being in love as much as it is going into full nihilism and giving up. It’s actually a narrative song where after being so burned out the character (he’s called literally Pink Floyd in the film The Wall which is a bit wank) is drugged by his manager and doctors so he can continue performing but because his depression is so encompassing he can only imagine himself as a militaristic fascist where destruction is all that’s left to him. “Comfortably Numb” is more about the end point of depression where it seems like nothing is left for you so you just give up and lose all feeling.

#15. “A Case of You” by Joni Mitchell
Album: Blue

This is another pretty straightforward heartbreak one by the lovely Joni Mitchell. As you want on a Joni song it’s accompanied by Joni’s weird chords giving it a real stripped down quality almost like you’ve intruded on her just plinking away. It’s arguable about who it’s about what matters is how sweet it comes across as she describes her lover and how conflicted the obsession over them makes her feel. Miles better than Bob Dylan fight me.

#16. “The River” by Bruce Springsteen
Album: The River

Here we go boys, The Boss. (Bruce not The Boss from Metal Gear Solid) (what am I doing?) So what we’ve got here a straight forward song about hope and possibility in your teenage years that get dashed when you make a mistake. One simple mistake has basically ruined two lives and they become stuck in a simple, unremarkable existence where they have an almost simmering resentment of each other and the eponymous river is both a symbol of the fun they had and a symbol of where everything went wrong. It’s about small town America and how the very obstacles and challenges of just existing can snuff out any dreams and where situations cause people to get stuck in cycles they cannot escape. It’s about mistakes and it’s about those mistakes owning you.

#17. “Shadows” by Chromatics
Album: It’ll be on Dear Tommy mark my words

You’ve heard of Chromatics even if you don’t think you have they’re - used in a hell of a load of shows but “Shadows” was most famously used in the Twin Peaks return and blows me away each time. “Shadows” is about how sometimes when you meet someone you’ve cared for there is an unspoken moment where you know it will be the last time you meet, last time you will be intimate maybe the last time you will both love each other. “Shadows” is a great song that will leave you broken up because it’s not hinting that there will be another chance, not even offering any hope, this is the last time.

18#. “Thursday” by Morphine
Album: Cure for Pain

Morphine are a weird one for me they were introduced to me by someone very important to me (“You Look Like Rain”) is probably a bit too close to me now, but Thursday is about an affair gone wrong. It’s actually a pretty violent sounding song about how the affair came to an end because of how careless they were, that the affair ended because of lust and as conflicted as the singer is about the woman he becomes callous at the end of the song making her out to be: “pretty good too” along with what he usually enjoyed some beers and a game of pool. It’s the end stanza that gets me, that a relationship became frivolous and she became just another distraction.

19#. “You’re The One” by Kate Bush
Album: Red Shoes

On an album full of heartbreak this is what Kate ended the album on. A ballad of a break up where she is collecting her things but still is madly in love with the person that has ended the relationship. Kate’s constant repetition of “You’re the only one I want” is so affecting because when you’re still in love with someone your brain just continues insisting that that person is what you need. Usually this kind of obsessive love is common fodder for men but here Kate shows that the obsessive nature of love goes both ways and that instead of moving on will reflect on not everything she learned but on everything she will lose.

20#. “In The Wee Small Hours of the Morning” by Frank Sinatra
Album: In The Wee Small Hours

Before anything let’s take a moment to admire how cool that album artwork is. Its pure pulp, pure noir, pure tragedy. It’s without a single doubt cool as hell. The whole album is inspired not just by Sinatra’s career crisis where his teen audience was moving on but his own tumultuous love life, particularly his marriage to Ava Gardner. The whole album is about lost love and heartache, but this is about the self-flagellation we do to ourselves thinking about our failed relationships. It’s a short song but every word is true you miss them most when you know they won’t be there again. This is every person keeping themselves up late into the night thinking of someone they love.

Finished (finally)

So there you go a list of criers for you to realise the futility of life and fleeting nature of love. A list that allows you to just curl up and softly weep into the abyss, or maybe it’ll make you feel happy. Who knows?

© 2019 JM

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