Three Great Songs About Heartache

Music is great for stirring up emotions, both good and bad. And if there’s anything songs are especially good at expressing, it’s L-U-V. So, you know, songs about being in love, about lost love, about falling in love, love shacks, love the one you’re with, lick my love pump, etc.

But the saddest ones for me, in a bittersweet way, are the ones about being in love with someone and then… maybe not so much anymore. Because sometimes whatever inspired that great passion just sort of fizzles out.

So here are my three great heartbreak songs for your listening, crying and eating a pint of ice cream 😀 pleasure:

Gordon Lightfoot is a Canadian singer-songwriter who, at 78, appears to be still very much active. In fact his web site displays his tour dates. (Smart guy – touring the South in the winter.)

Short of the entire catalog of Frank Sinatra in the ’50s’s, I maintain there’s no greater song than “If You Could Read My Mind’ about loving someone and then later seeing them as, what, a friend? A roommate? An acquaintance?

The whole things works – his voice, the guitar, the lyrics, the strings, the pathos:

“I never thought I could feel this way
And I’ve got to say that I just don’t get it
I don’t know where we went wrong
But the feeling’s gone and I just can’t get it back.”

Dave Mason has a long and storied history as a performer – with Traffic, recording with Hendrix (All Along the Watchtower) and as a solo artist. A frequent performing partner of Mason’s was the late, relatively unknown songwriter Jim Krueger. Krueger wrote the song “We Just Disagree,” out of, one assumes, some love affair gone wrong.

Again, everything works: guitar, strings, Mason’s plaintive voice. Kreuger plays twelve-string and sings harmony. But it’s Mason’s tune all the way:

“So let’s leave it alone
‘Coz we can’t see eye to eye
There ain’t no good guy, there ain’t no bad guy
There’s only you and me and
We just disagree.”

Back in the turbulent year of 1968, Simon & Garfunkel released a terrific album called Bookends. The then twenty-seven-year old Simon chose to write a few songs about old age on this album. “How terribly strange to be 70,” the now seventy-five-year old sang. Much greatness on this album. But the tune that always stops me in my tracks is the beautiful, haunting, “Overs.”

This song is not only about falling out of love, it is about falling out of love and growing old. (Screw the ice cream. Shot of whiskey, s’il vous plait.)

“We might as well be apart
It hardly matters we sleep separately
And drop a smile passing in the hall

But there’s no laughs left
‘Coz we laughed them all
And we laughed them all
In a very short time.”

So. What are some of your favorite heartache songs, especially ones that involve “Yeah, um, any way we can just be friends from now on?”

29 thoughts on “Three Great Songs About Heartache

  1. When it comes to weepies, If You Could Read My Mind is one of my all-time favourites. There must be some Leonard Cohen songs that have that so-sad-it’s-over feel, too. So Long, Marianne comes to mind.

    Your request for other songs in the same vein reminded me (strangely) of a novelty song from way back (early sixties?). I don’t know its title or the artist, I only remember the general gist and a few of the words. The singer keeps bumping into a strange little man with a squeaky cartoon voice whose only words are “I want you, I want you, I want you to bits”. Then, after three or four verses, the little man changes his tune and, in the saddest voice you’ve ever heard from a cartoon character, he says, “I don’t want you any more”. And there the song ends.

    I’ve tried to find a bit more about it but Google has failed me.


  2. Yes, that’s the one! I obviously mis-heard the words. I’m still a bit puzzled, though. I’m sure the version I knew as a lad was sung by a man and Mrs. Crotchety backs me up on that. I can only find the Betty Johnson and Pet Clark versions, though. Oh well, that’s a puzzle for another day…


  3. Yes, and I think I’ll not travel down that particular rathole. 😀 Even deeper research may ultimately turn up that mystery fellow, er, bloke.


  4. The new Ryan Adams album Prisoner is two sides of heartache. Dylan’s ‘Tangled Up In Blue” is a wonderfully oblique song about heartache.


    1. Don’t know the Ryan Adams one but I’ll check some of it out on YouTube. And yeah, “Blood on the Tracks” is one big heartache. “Blue” by Joni Mitchell too now that I think of it.

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    1. Love that one. I was just listening to that as part of the “Tracks” album. I was catching up on that to review it for our fellow blogger over in England. Beautiful, beautiful song.


  5. You got CB reaching for the Kleenex. I thought I’d get current and pop in on this. Here’s the coincidental thing again with your takes. I have a 3 disc set of GL that I was listening to on the weekend and you do this. I hung in with Dave Mason after Traffic and dug his stuff. Some really good tunes from the comment gallery.


      1. ‘The Original Lightfoot: The United Artists Years’. His 5 albums he recorded between 1965 – 69. Your cut came after. All the albums were remastered for this disc.


        1. Lightfoot? I’d say not really, no. But it isn’t about dislike or lack of interest in him per se. It’s just that I’m not a superfan of “man with acoustic guitar plays meaningful songs.” Apart from Dylan, James Taylor, Springsteen’s acoustic stuff, never have been. Just doesn’t float my boat. I like a band. And BTW, a full band. I don’t dislike White Stripes, Black Keys and their ilk. But enough of the drummer/guitarist thing already.

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    1. Sure, Prine is good. Falls into the category of “probably wouldn’t buy but will listen if he’s on the radio.” Again, not really my genre.

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  6. You have a pretty open mind from what I’ve gathered. Having Gordon at the top of this take proves it. Keep it up. Can’t get Gord’s song out of my head. At least it’s a good tune.

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    1. I try to listen with a fresh mind. But I just don’t like everything. Who does? I tried to listen to Kanye West the other day. Whatever other people hear I’m not hearing.

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      1. Obviously I’ve heard the name but couldn’t whistle his tune. He’s the guy you said cut a song with McCartney. CB try’s to keep it positive. I just don’t comment if I haven’t heard something or it doesn’t do it for me. You and I could talk music for hours. Maybe one day if I’m ever in Boston I’ll take you for a few brews and tell you what I really think. ‘Bear Creek Blues’ some tasty licks for you. Johnny Prine

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  7. It’s just that I’m not a superfan of “man with acoustic guitar plays meaningful songs. I thought I’d get current and pop in on this.


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