Miserable Bastard Music: Top 10 Sad Songs

All my favourite music is pretty miserable, cheery choons just don’t cut it for me. My good pal Silv recently compiled her Top Ten Miserable Bastard Songs and it got me thinking what were my favourite Debbie Downer melodies? This is actually 11 songs because I couldn’t whittle it down any more, there are loads I could chuck in, I just love sad music, it’s kind of antisocial but I can’t get enough.

There’s Bill Callahan, obvs, the way The Supremes’ Diana Ross sings Where Did Our Love Go with a dead-inside faux sincerity, all of the Tindersticks’ back catalogue and especially I Was Your Man which includes the total heartbreaker of a line ‘You’ve got a smile that never reaches your eyes’, as well as Smokey Robinson and the Miracles’ I Gotta Dance To Keep From Crying which presses all my happy/sad buttons.

Thanksgiving – Rich (Homeless)
I was introduced to Thanksgiving by a friend and Rich (Homeless) is the king of dead-inside misery. Mumbled lyrics and and set of swooning backing vocals, it’s like a lullaby to death. Adrian Orange sings ‘I’m gonna spend my life up, until I die’ and you want to join him. Best listened to slightly drunk, fully clothed, lying on top of the bedcovers.

Judy Collins – Early Morning Rain
There’s a lot of versions of this folk classic around but Judy Collins’ has always been my favourite, I like the way this sad but strangely hopeful tale of skipping town is at odds with Judy’s prim voice.

Bonnie Prince Billy – Wolf Among Wolves
Bonnie Prince Billy’s entire back catalogue qualifies for Miserable Bastard status but Wolf Among Wolves stands out, an intimate song with his gentle voice asking to ‘be loved as what I am, a wolf among wolves, and not as a man among men’. Indeed.

George Brassens – Putain de Toi

A lot of sad songs I like could be conceived as being quite cheery, this is a prime example with its jolly self-pitying chorus of ‘Ah-ah Putain de toi, ah-ah-ah pauvre de moi’ which roughly translates as ‘ah-ahh you fucking bitch, ah-ahh poor me’, one part FU, one part sadness, one part LOLs. George Brassens cheerfully sings his way through this ditty about his girl who ran off with the butcher, you can find a full translation here.

Julie Doiron – Oh These Walls

Julie Doiron is just brilliant, her gentle, despairing voice doesn’t really need anything more than a piano. Oh These Walls is a lovely shoutout to a missing partner, with the claustrophobia of being cooped up inside a room. If I close my eyes when I listen to this I can see damp, red-painted walls with a mattress on the floor, total Elle Deco nightmare.

Walker Brothers – Sun Ain’t Gonna Shine Any More
The Sun Ain’t Gonna Shine Anymore by the Walker Brothers is classic high-drama misery music. It’s such a bombastic song that it has a cathartic effect on me, something like the change in atmosphere after a rainstorm. Makes me want to wear a tabard in a 1930s semi and weep while Pledge-ing the coffee table.

Laura Cantrell – Churches Off The Interstate
Laura Cantrell is another great Voice and second entry for cheery sad music. Jaunty melodies and heartbreaking lyrics always slay me, which is probably why I’m such a country music fan. Churches Off The Interstate used to be a John Peel favourite which is kind of sad in itself, and it also has a similar ‘ain’t no other way than up from here’ vibe like Early Morning Rain.

Karen Dalton – In The Evening (It’s So Hard to Tell Who’s Going to Love You the Best)
Karen Dalton, what can you say? Something On Your Mind is a big contender, but I like her version of the blues classic In The Evening (It’s So Hard to Tell Who’s Going to Love You the Best), it’s usually done as quite a manly, twangy song but she pares it down to a dribbly drawl, a morning’s lament to a night of regret.

Casiotone For The Painfully Alone – Tonight Was A Total Disaster
You can’t have a miserable bastard playlist without some Casiotone For The Painfully Alone, the tragi-comic lyrics and bedroom keyboards all scream ‘pitiful loser, you better laugh at yourself before someone else does!’

Elizabeth Cotten – Oh Babe It Ain’t No Lie
Left-handed guitarist Elizabeth Cotten was born two centuries ago (!), learnt the guitar as a child and then relearnt again in her 60s. This little song is a cosy little FML ditty.

Mount Eerie – Ancient Questions
Mount Eerie’s ‘Ancient Questions’ is as beautiful as it is sad; a bleak, misty ode to a dream. Phil Elverum has a despairing voice that gives up hope before he even finishes his sentence. Womblike bass and ‘nothing means nothing’ lyrics make it another strong contender for lying on top of the bedclothes, fully dressed.

You can listen to all these songs and more on my Miserable Bastard Music playlist, but maybe go and listen to this and look at some cute kittens after, yeah?

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3 comments to Miserable Bastard Music: Top 10 Sad Songs

  • Tu connais Bill Fay? C’est terrible comme musique. Et aussi le dernier album de Françoise Hardy, “L’Amour Fou” est un peu mortifiant.

  • gracie

    I can’t seem to listen to your spotify here, (it only launched in Ireland yesterday) but I listened to some on youtube – Mount Eerie, oh so beautiful! I love sad music the best. I once made a mix for a friend and the next time I saw him he looked at me full of concern and said – ‘Gracie….are you OK?’ Never better!

  • Haha! Hope it’s working now, love some musical downers

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