Saddest Songs About Breaking Up

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Breaking up is something that, unfortunately, a vast majority of people will go through. And that includes – obviously – songwriters. Break-ups create art and break-up songs have created some amazing pieces. But then there are the break-up songs that really tug at the heart-strings. These are not just about a sad time, but they induce sadness in those who listen. These are the songs that really get the listener.


Certain things make a song sad – lyrics that strike a chord, a slow tempo designed to sound sad, lots of minor chords, a delivery that sounds heart-felt and honest, and, of course, the personal connection. To my mind, if you get any 3 of those, you have a sad song. Some songs are just too upbeat or too sing-along to be really sad songs. The guitar solo is too awesome, the piano playing is just too intricate, there's a degree of hope in the lyrics – all can take the song out of genuine sadness-inducing.

I know, I'm being picky. But to my mind, sad songs about relationships that have gone sour bring out personal, painful memories. They make you sit in your room, holding a pillow and staring at nothing. They make you think that seventh bourbon on the rocks is a good idea. They make you curl up with your teddy bear and cry yourself to sleep. Or so I've been told. In the end – they bring out sad emotions.


So, here's a few songs about breaking up that I think are amongst the saddest.
Billy Field – You Weren't In Love With Me

From the opening lines, this song tells you the singer is sad and there is nothing that is going to help him. The piano playing is sublime and the singing sounds like it's being ripped from the depths of his soul. And the sentiment of the song – "I was in love with you but you weren't in love with me" – is something that makes it all too relatable. This is one of the songs on my own personal list as well. When I lost Barbara, this is one of the songs I played on constant rotation (I've mentioned a few others in past columns here), but had to stop because it made me break up every time. Yes, I do still miss her – why do you ask?

Willie Nelson – Always On My Mind

Now, I love the Pet Shop Boys' cover version. And Elvis did a good shot at it as well. But when you listen to Willie Nelson sing this song, you know he wrote it because he feels it. The sparseness of the production adds to the feel of it – one man and a guitar bemoaning the woman he mistreated and drove away. Really, really sad and really, really well done.

Abba – The Winner Takes It All

Hard to imagine any Abba song being sad. The pop sensibilities of Benny and Bjorn – the songwriters – are amazing and their works are surprisingly intricate pieces. But this song… Not sure what it is about the song, but it always gets to me. It's probably the delivery. Written at a time when the group themselves were going through internal marriage break-ups, that is most likely why it feels so real. And even though it rises to a crescendo at the end, to me that is almost a cry of passion. This is an awesome song.

Roy Orbison – Crying

Roy Orbison's voice is one of the great ones in modern music. And when he turned it to the sad song, he could make the listener feel it was about him or her and them alone. But of all his songs, the saddest one, the one that sends shivers down the spine, is 'Crying'. Many have covered it (some very well – Don McLean for one) but none have matched the original for sheer emotional impact. Again, his ending notes sound like a keening wail of a man in pain. That spine, those shivers… wow.

Adele – Hello

Adele is one of the very few modern singers who can actually sing. Her voice is amazing, an instrument all of its own, and she doesn't need studio trickery to sound awesome. And maybe that's why this song works as such a sad song. She sings it with passion and conviction. The lyrics have a sense of hopeless desperation and they are delivered with such feeling it is hard to ignore the spine-tingling that comes from Adele's voice. One of the best songs of the modern era.

Jim Diamond – I Should Have Known Better

A song that should maybe have been in my One Hit Wonders column, but I like it as a better fit here. The song about a man who knows he's been a bit of a moron in the relationship and is trying to convince his girl to come back to him but – judging by the impassioned delivery as the songs reaches its crescendo – fails is just brilliant. And, again, for me, there is a personal connection. I bought the 45 (yes, vinyl) when I lost Clare's friendship… and listened to it once, cried all night and didn't listen to it again for 6 months. It got to me that much. So, on this one, your mileage may vary, but to me… it's sad. And yes, I also still miss Clare…

The Walker Brothers – The Sun Ain't Gonna Shine Anymore

The delivery makes this song. From that opening word – "Loneliness…" – sung in that incredible bass voice to the soaring chorus, it grabs the listener and does not let them go. Who can't relate to the sentiment – when you're this sad, it does feel like the sun is not going to shine again. But I do think this is a case of the singer making the song. That delivery… wow.

Laura Branigan – Ti Amo

Laura Branigan is under-rated. Most people look at her as a one-hit wonder ('Gloria'), but she had so many great songs before her tragic death. This is one, and this one is another song I bought on 45. There was no personal backstory, I just really liked it. It's a song that builds slowly. And the repeated lines seem to have been drawn from within my own head at each and every break-up: "Ti amo, God how I love you so." That heartfelt line, coupled with her awesome voice – not perfect, but great and real – makes you feel like she is singing for you.

Harry Nilsson – Without You

Harry Nilsson is best known for getting drunk with John Lennon in the 1970s, which is incredibly unfair to a talented singer-songwriter. And this song is a testament to his talent. The lyrics clearly state he wants his girl back, but that there is a good chance it's not going to happen. And the way he delivers "Can't live, if living is without you" to that almost screamed "Can't live!" always makes me stop short. He felt this song when he sang it; the listener feels it when they listen.

Gordon Lightfoot – If You Could Read My Mind

This song is about the process of breaking up. The lyrics indicate that the singer realises the relationship has run its course and he doesn't think it can be saved. It is so sad and filled with depression and there is really not a sense of hope about this relationship at all. And, if you want to hear it delivered in a slightly different but no less heartfelt manner, try Johnny Cash's version from American Recordings V: A Hundred Highways. This indicates two things – the lyrics are awesome and Johnny Cash's ability to interpret songs on the American Recordings series was second to none. But still, Gordon Lightfoot wrote and performed a sad song

And there you have it. What songs have I missed? What songs do you find the saddest? Hit the comments section below!

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