Five of the saddest songs you’ve never heard
They say misery loves company, and that may well be true. But one thing misery certainly loves is a soundtrack of songs that are just as sad as whatever caused the misery in the first place.
Who knows why we do it to ourselves – it could be a break-up, it could be that our favourite pet just got buried in an old shoe box in the garden, but no matter why, we are devastated, we seem to have to seek out music to go along with it.
Usually, of course, it is love that’s the root cause of human sadness, love and loss. And both themes have been turned into some of the finest and most famous songs in musical history. Think ‘Love Will Tear Us Apart’ by Joy Division, ‘Everybody Hurts’ by REM, and Sinéad O’Connor’s ‘Nothing Compares 2 U’.
Apparently, according to Psychology Today, we love sad songs because paradoxically they make us feel happy*, observing that because we avoid misery in our daily lives, we are drawn to it in art.
Our desire to wallow in self-pity is only matched by our desire to find a suitable musical accompaniment, so with that in mind, here are five desperately sad songs that you likely don’t know, but that will have you reaching for the tissues. Sad tissues obviously.
*These songs won’t make you feel happy.
The five saddest songs you’ve never heard:
Amigo the Devil – The Mechanic
Anyone who has ever begged someone for one last chance will know how desperate it sounds, and this song is that emotion put onto record by Miami singer-songwriter Danny Kiranos.
Far more involved than simply a ‘please don’t go’, this recognises the complex emotions at play in a failing relationship, with memorable lines including: “Like a house that’s on fire but you love how it feels, so you throw in the memories to feed it”.
Tragically, a year later, life imitated art and Kiranos lost all his possessions in a house fire, stating online: “Everything is gone.”
Keaton Henson – Prayer
British musician Henson lost his father in 2020 and felt inspired to record this almost whispered, piano-backed falsetto that speaks of being left behind by a loved one, child-like almost: “While you shed your skin, and I read myself to sleep.”
After the delicate prayer has collapsed into a staggering string section, you are left with a fading, actual recording of Henson’s late father on a home movie, entreating his son to “Wave to daddy”.
Impossible to get through without a lump in the throat.
The Blue Nile – Family Life
By a country mile the most upsetting Christmas song ever recorded, Glasgow’s Blue Nile placed this story of domestic violence as the closing track on their 1996 album Peace at Last.
As singer Paul Buchanan recalls a wretched childhood with devastating lines like “Jesus please, make us happy sometimes”, the music swells with almost ironically Disney-esque strings and the narrator prays the tale of pain won’t be repeated now he’s grown up, “For my kids, for my wife”.
Harrowing, but beautiful stuff.
Randy Newman – I think it’s going to rain today
Spectacularly bleak, this was still such a fine piece of songwriting that it was covered by Barbra Streisand, Nina Simone and Peter Gabriel.
The original is the best, though, Newman’s stunning orchestral arrangement underpinning his depressed confessions, detailing observations like “Tin can at my feet, think I’ll kick it down the street, that’s the way to treat a friend.”
Despite the ‘human kindness overflowing’, Newman cannot find even a modicum of cheer.
Neil Diamond – Another day (That time forgot)
Hidden away on Diamond’s Rick Rubin-produced 2008 album Home Before Dark is this incredibly sad gem, a duet between the legendary singer and country star Natalie Maines that details the anguish of a break-up, from the point of view of both sides.
To a simple, strummed guitar and tumbling piano line, each singer battles with the ‘should we, shouldn’t we’ of bringing things to a close, including a final sleep-deprived coalescing, until eventually just the painful realisation is left, with the pair simply repeating: “Oh no”.
