The Top Ten Saddest Songs Ever….
plus another 5
Ten chosen by Ged Babey from LTW as a promotional device for the forthcoming album by cult indie legend DAVEY WOODWARD – the Bristolian (on Last Night From Glasgow out in Sept 2026) which includes ‘some of the saddest songs I’ve ever heard’. There are some lighter ones: love letters to Bristol, but it could well be his equivalent to (Lou Reeds monumentally sad masterpiece) Berlin. Davey picks his Five favourite Saddest Songs Ever.
Everyone loves ‘a list’, but this one will leave you in tears.
Sad Songs are popular. They sell – if the artist is well-known and part of the music industry machine. Like the so-called misery memoir. But plenty of niche, cult artists with modest sales bare their soul and share their pain – and like all great music, help the listener feel ‘less alone’ ….
This isn’t a serious, academic study of the Sad Song – it’s a list, with some commentary, to help get Woodwards album some attention – and the Number 1 is almost universally agreed upon, after a quick Facebook Survey…. You, dear reader will have plenty of whattaboutery and additions I’m sure. There is nothing by the Cure, the Smiths, Radiohead or Nick Cave. I have chosen some old and some new songs and asked for Daveys input. He chose another five and we discussed the choices.
Stating the obvious, there are three elements and how they combine, that make up these Sad Songs: the words/narrative – usually about death/grief or loss. The music – must contain its own melancholic vibe and air of its own. And the vocal delivery – is loaded with the emotion -and/or- has a strange detachment.
The first ten are my choices – in no particular order, apart from the first…
Johnny Cash – Hurt
I don’t even need to say anything, do I? It’s been written about endlessly. Is the original better? No, Johnny gives it a gravitas because of his age and health and dignified delivery. Musically it is perfect, imbued with just as much sorrow and pain as the words.
(Davey Woodward) The images of Johnny and June Carter in the video made it even more poignant. The album its on ‘American IV’ has a bunch of covers that Johnny manages to Imbue with a hellava lot of sadness, including Ewan MacColl’s ‘The First Time Ever I Saw Your Face’, listen and weep.
Misty Miller – Best Friend
Most of you won’t know this one. Written by the teenage Misty when her childhood dog was on it’s last legs, sleeping a lot and she realised they wouldn’t be around much longer. Its such a simple, heart-breaking song that all dog-lovers will relate to no matter their age. Misty is part of the Brixton Windmill scene and releases occasional brilliant songs like this other masterpiece of sadness and resilience.
(Davey Woodward) We love our pets like we love people, so yes, we really feel sadness and loss when they are gone but for whatever reason I don’t connect with this song. Sorry Ged and Misty!
Lou Reed – The Bed
You could pick any of the other songs from Berlin – but this is the one that will always reduce you (me) to tears. Musically stark and intimate with the end section a swirling choral coda that ascends to the heavens.
(Davey Woodward says) Agree with you, it’s so hard to choose from this album as all the songs are sad. If pushed I’d probably go for Caroline II.
Lisa O’Neill – The Wind Doesn’t Blow This Far Right
This song encompasses so-much but the two key lines which imbue it with humanity and sorrow are the friend who ‘passed without saying goodbye’ and the ‘beautiful children – starved to the bone’.
(DW) I didn’t know about Lisa until you posted her songs, wow how did I miss her music for so long? So thankful to hear her. Her song ‘Old Note’ really gets to me. It’s the sound of her voice; it just emotionally clicks with me.
The Shangri La’s – Never Go Home Any More
A toss-up between this and the better-known Past, Present Future but the line: She grew so lonely in the end / the angels picked her for their friend gets me, every single time. A mother who dies of heartbreak is a sure-fire tearjerker.
(DW) Classic 60s broken heart song with a twist. I love the spoken word aspect of the song and the drama of the orchestral parts. I imagine Jarvis Cocker listened to this song on repeat.
European Sun – The Space She Left
From the recent When Britain Was Great album. The music is odd and seems to play-itself and the lyric – the complete opposite to toxic masculinity.
(DW) A really atmospheric song, quite psychedelic too. I like the vulnerability.
Black Box Recorder – Child Psychology
A very ‘arch’, dark-humoured song. Not one based on first-hand experience I would imagine. But cinematically and voyeuristically sad, in my opinion. Billie Eilish single-handedly resurrected the band due to the song.
(DW) Completely get selective mutism, we all been there yeah? The innocent voice, the chorus is so catchy and yes lyrically dark. In a strange way I find this song quite soothing.
The Carpenters – Superstar
Sonic Youth did a fantastic cover version of this – but I have come to love the original (with thanks to Graham Henry). I can hardly wait to be with you again… is the killer line, but the assumption is that the lover is dead, when perhaps it was never 100 per cent intended to be interpreted as such.
(DW) I’ve got a lot of time for the use of the word ‘baby’ in a lyric because it’s really hard to make ‘baby’ sound good in a song. The Carpenters can. The ‘baby’ bits are pure pop. Just a great song, great singer. Great Orchestral arrangement. Does it make me feel sad? Not really.
The Singing Loins – So Long, my Old China
A song about remembering a dear old departed dad, the generation gap… and extra sad now that Chris Broderick is no longer with us.
(DW) Folk, football and death, what it’s like to lose a dad that you loved, evocative vocals, authentic, raw, a lovely sad song
Davey Woodward – We Are Leaving You
The first song made public from the forthcoming album. The way it is recited is as beautiful and emotional as any sung vocal. The music is simple, perfect and gives the story a resonance that is full of regret and sorrow. There are darker and more heart-rending songs on the album which almost make this one sound like an upbeat banger.
DAVEY WOODWARDS TOP 5 CHOICES
Fairport Convention. Farewell, Farewell,
(DW) Being a happy go lucky type of guy I often go through lists of tunes I might have playing at my funeral. This one consistently comes up; it’s such a beautiful sad song. I have also considered Charles Penrose ‘The Laughing Policeman’.
(Ged Babey) I’ve always had the Velvets I’m Set Free in mind for my funeral song. A friend of mine actually had William Shatners version of Spirit In the Sky at his. ‘When I die and you lay me to rest…’ It was surreal, hilarious and heart-breaking all at the same time.
Karen Dalton. Something On Your Mind
(DW) Maybe this is the saddest song of all time, as with Lisa O’Neill it’s the voice that does it for me, not really the words but the sound of Karens voice. There’s is something so achingly sad in the way she sings this song.
(Ged) I’d heard the name, but never listened to her before. It is beautiful and her voice unique. Courtney Barnett sums it up well here.
Joy Division – New Dawn Fades
(DW) The sound of being lost. I was 19 when ‘Unknown Pleasures’ came out. I was drawn to the melancholy and the futuristic new sound of the band. After Ian Curtis died, I stopped playing their albums. I’m very superstitious, I thought something bad would happen to me if I played them. In recent times the band are all over the radio so I hear their music that way.
(GB) I always thought, and said, that Joy Division were ‘over-rated’ because I preferred ComSat Angels and The Sound at the time. But I have to admit now, that they really weren’t. This ‘reimagined video’ by the way is fucking appalling.
Neva Dinova – Hat Oer Eyes
(DW) First came across them with the joint album ‘One Jug of Wine, Two Vessels’ with Bright Eyes. This song is about isolation and trying to change, again the voice is beautiful and the simplicity of it with an acoustic guitar makes for a beautiful sad song
(GB) Sorry – the voice doesn’t appeal to me and its a real wallow-deep. More self-pity than sadness.
Little Ann. Deep Shadows
I needed to put a Northern Soul tearjerker in this list, so many great female singers in this genre get overlooked. Here’s another fantastic voice, sensitive but powerful with a stark musical arrangement. It’s an end of the night hold your partner close to you on the dancefloor number. I imagine they put their head on your shoulder, you can feel their breath on your neck, maybe it will be the last dance you both ever have.
(GB) That’s a great song. Thanks for your choices Davey. Hope it wets the publics appetite for the Bristolian… Did you set out to write an album with some of the Saddest Songs Ever on it?
No, I really didn’t. Most of its accidental, but I guess I was reminiscing a lot with these songs and that generally takes me to difficult places and I guess we’re living in difficult times right now too, so maybe that’s why the album has that sad melancholic feel?
It also has a lot of beauty, humanity and occasional flashes of humour as well though. I really do think it’s a masterpiece….
PRE-ORDER THE BRISTOLIAN by DAVEY WOODWARD
Daveys back catalogue on Bandcamp
All words Ged Babey.
Davey Woodwards input in italics, many thanks to him.
If you have been affected by issues raised this piece you need to listen to this.
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