Beautiful Songs About Heartbreak and Regret

A couple of months ago, I ran across the Pentatonix cover of Hallelujah. It’s a beautiful rendition… except for one problem which really got under my skin: The lyrics are clearly about heartbreak, yet, just when the vocal line should be falling in despair at the end, they instead soar in adulation. (And then they put it on their Christmas album, which was what convinced me they didn’t get it.)

That got me thinking about recordings which are beautiful and do handle this sort of “internal sarcasm” motif properly.

Rufus Wainwright’s cover of Hallelujah
You’d be surprised how many singers screw this song up in ways subtle or very obvious, but I’ll get back to that. First, a little lesson on the complicated history of this song.
The initial recorded version by Leonard Cohen is a very different beast from what has entered the popular culture today. Cohen used a significantly different set of lyrics, his overall timing and style are quite unlike the lonely, heartfelt piano and solo vocals people have come to expect, and he would mix the lyrics up during his live performances. (According to Wikipedia, he originally wrote roughly 80 draft verses for the song and Cohen himself felt that”many different hallelujahs exist”.)
The overall effect being a song that feels more like Cohen has decided to wash his hands of emotion altogether and the backup singers are celebrating it, but the lyrics here are so different that I can’t accept this as the origin of the Pentatonix version.
The song as people today recognize it, which aims to concentrate its emotional impact as an expression of solitude and despair, owes most of its origins to John Cale’s version.  The solemn, soulful tone, prominence of piano, and the recognizable set of lyrics we see in covers today all originate here, with the cover Cale recorded after asking Cohen for his notes.
However, while Cale’s version is beautiful, Wainwright’s version has shown that there was still room for improvement. For example, while Cale sings “It’s not the cry that you hear tonight“, reminding you that you are party to a performance, Wainwright sings “It’s not a cry you can hear at night”, a more abstract statement about the nature of the emotions themselves. (Update 2020-08-11: Apparently Cale only does this first part in his live performances, one of which I saw a recording of, not his studio ones, making my complaint with it moot.) On a similar note, while Cale plays a few bars of piano at the end as a final performance, Wainwright allows his voice and the piano to trail off together at the end (leaving you to almost expect him to begin to sob before the recording cuts out). Both of Cale’s choices may be fine for audiences in a live performance, but risk harming the immersiveness of the piece when used in a recording.
Other, more subtle issues in Cale’s version include: First, Cale sings “and love is not a victory march” (compared to Wainwright omitting that first word, allowing the mind to fill in the more appropriate “but”). Second, Cale refers to “the holy dove” when Wainwright’s “the holy dark” feels more fitting with the implied sexuality of the “and remember when I moved in you” that it follows. Third, unless I very much misunderstand his accent, Cale sings “her beauty an’ the moonlight overthrew you” while Wainwright’s lyrics can be easily heard as “her beauty in the moonlight overthrew you”… another minor change that seems more fitting to me. Finally, Cale’s version still carries some of Cohen’s laid-back, loose lyrical timing which Wainwright tightens up, producing a song which has finally fully transitioned to the role it had started to take on.
So, with that done, what did I mean when I said that so many singers screw the song up? Primarily that they make changes to how the song is performed which weaken its impact because they misunderstand it. Most unarguably, the insertion of words which throw off the rhythm of the piece, such as singing “she broke your throne; she cut your hair” as “she broke your throne and she cut your hair” but, also, meddling with the pacing and the insertion of vocal flourishes meant to show off their voices at the expense of the song’s immersion.
To make a long story short, even Cohen himself encouraged the proliferation of many different versions of this song, but there’s a difference between crafting a new interpretation of it and making small tweaks to an existing one… and Pentatonix followed Cale’s version so closely aside from their ending that I can only say “Wainwright did this interpretation best”.
Dunrobin’s Gone by Brave Belt
Now, let’s move on to a more clear example of an “inner sarcasm” regret song.
In this song, by the precursor band to Bachman-Turner Overdrive, the vocalist sings about his difficulties letting go of what he had as “a voice inside my head keeps on screaming” that, judging by how he treated his girlfriend, driving her away must have been his intent and, therefore, he must be happy now.
No big fancy history or analysis this time… just a beautiful song that fits the theme.
Where I Went Wrong by The Poppy Family
Now for something slightly different. In this musical monologue to a fellow passenger on a bus, a cold, lonely, and tired Susan Jacks sings about how “the one that used to talk to me” doesn’t want her, blaming herself for trusting him and wishing for the temporary relief of sleep.
One could almost think that the character in this song was tailor-made to be the girl who “ran” from the character in Dunrobin’s Gone.
Again, nothing fancy… just something beautiful and on-topic.

Well, that’s all that came to mind right now and I don’t have time to go researching, so I’ll probably wind up adding more as I think of them. As-is, I welcome suggestions.

CC BY-SA 4.0 Beautiful Songs About Heartbreak and Regret by Stephan Sokolow is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

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2 Responses to Beautiful Songs About Heartbreak and Regret

  1. Jane says:

    Margaritaville, by Jimmy Buffet
    Another song about a man who has realized his part in a break-up. Her departure appears to have left him despondent, wasting his time in a beautiful paradise, drinking to kill the pain.

    • A beautiful song and definitely topical, but it doesn’t really “do it” for me so I may or may not add it to the post proper. It’ll depend on what else I manage to dig up.

      Thanks either way though.

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