Readers recommend: songs about failure

What is it about writing songs about their weaknesses, losses and disappointments that some musicians find so attractive? Failure is ahuge, painful subject, but it's one that at least comes with some sort of end point attached. Perhaps, in the midst of the bleakness, that finality offers some comfort. This week we've got career failure,

Readers recommendMusicFrom sexual failure to the death of hope, musicians just can't seem to stop dwelling on the negatives

What is it about writing songs about their weaknesses, losses and disappointments that some musicians find so attractive? Failure is a huge, painful subject, but it's one that at least comes with some sort of end point attached. Perhaps, in the midst of the bleakness, that finality offers some comfort. This week we've got career failure, sexual failure, a failure to deal with a growing – and crippling – addiction, failure to recognise when things are good and when things are bad. What they all have in common is that sense that there is some finality in failure, some strength to be found in letting it all go.

Roger Daltrey refused to sing Pete Townshend's However Much I Booze, claiming, quite rightly, that it was far too personal for him to do it any justice. The story of a man who feels utterly trapped by his galloping alcoholism ("I don't care what you say, there ain't no way out"), the song is a plea for help as well as an admission of defeat. "I just can't face my failure," Townshend sings, "I'm nothing but a well-fucked sailor."

John Lennon's I'm a Loser is a remarkable timepiece – a song that is half the past (the Carl Perkins shuffle) and half the future (the self-lacerating Dylanology). "My tears are falling like rain from the sky," he sings, "is it for her or myself that I cry?"

Billie Holiday's whole life was a slow ride to painful failure, and Sophisticated Lady is an unutterably sad vision of someone who has everything she wants but nothing she actually needs. "Diamonds shining, dancing, dining with some man in a restaurant," she sings, "is that all you really want?"

How many times have you heard Love Will Tear Us Apart? Listen to it again – it's still an incredible song. "Do you cry out in your sleep," Ian Curtis asks, "All my failings exposed?"

Phil Ochs's song looks at his own failing career. There's no crash and burn, no drama, just this quiet recognition of his own creative failure. "Farewell my own true love, farewell my fancy," he sings. "Are you still owing me love, though you failed me." Swans, meanwhile, offer a magnificent hymn to crushing futility. "My hands are firmly tied," they brood, "to the sinking lead-weight of failure."

Nick Drake had only recorded one LP when, aged 22, he seems to have declared himself a failure. "Could have been your statue," he sings on One of These Things First, "could have been your friend/ A whole long lifetime could have been the end". Gil Scott-Heron looks at the wastage in his community and sees only failure. "I know you think you're cool," he sings, "just 'cos you shootin' that stuff in your arm, it don't matter what pine box you choose." Sigur Rós's Agætis Byrjun tackles their disappointment at how their first record sounded, a small but significant failure tempered by their promise to themselves to "do better next time".

Finally, Mike Altman was only 14 when he wrote, "Suicide is painless, it brings on many changes, and I can take or leave it if I please," and nailed the most painful failure of all: the failure of hope.

This week's playlist

1 However Much I Booze – The Who

2 I'm a Loser – The Beatles

3 Sophisticated Lady – Billie Holiday

4 Love Will Tear Us Apart – Joy Division

5 Rehearsals for Retirement – Phil Ochs

6 Failure – Swans

7 One of These Things First – Nick Drake

8 The Get Out of the Ghetto Blues – Gil Scott-Heron

9 Agætis Byrjun – Sigur Rós

10 Theme from M*A*S*H – Johnny Mandel and Mike Altman

Next week: songs about holidays

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