It’s funny what moves you when it comes to a lover. Sometimes, it’s a cup of coffee in the morning or her lingering smell when she leaves for work. Other times, it’s the way she leaves a soapy note on the mirror in the bathroom or just the remembrance of a nice, firm set.

Regardless, artists have striven to capture those moments and the reasons for their ultimate demise. Here are five of the most poignant, heart rending songs about lovers pining for what will never be. None of these choices involve death because that removes any culpability on the part of the hero or heroine. Instead these songs ask the question, “Where did I go wrong?”


I Used to Sing for You - Tracy Chapman

It’s a rare, rock and roll women who sings about love and loss. Usually, we get tirades or revenge songs with lyrics like, “Earl's gotta die, “ by the Dixie Chicks or “Dickhead“ by Kate Nash. Incidentally, aren’t they the epitome of composed, political restraint?

Ms. Chapman, on the other hand, with a guitar and her portrayals of a disconsolate mood are almost impossible to top. In “I Used to Sing for You,” she takes the simplest of moments, humming a song in bed, and  transforms them into analogy for the power in the entire relationship. She sang, he listened. She had the power but she gladly gave it away, but it meant nothing to him and he walked. Unbelievably powerful stuff.


Is She Really Going Out with Him? - Joe Jackson

This song is more typical of the current view of male prowess when it comes to love. The dyspeptic hero is at a loss to explain his inability to compete with an obviously inferior member of the human race.

The worst part is not that it never ends for this guy but that it never gets started in the first place. Our hero never understands that it is better to have loved and lost than to never have loved at all.

All that’s left is to lament that, “There’s something goin’ wrong around here.” Cut to the bass line.


Here Comes My Baby - Cat Stevens

Don’t even try to correct me about the Yusuf Islam nonsense. That version of the man is a travesty of his former self. For thirty years, after phenomenal success, Mr. Stevens kept up the charade that he was a devout Muslim. Then the money ran out and he immediately prostituted himself for any ad campaign available.

Nevertheless, his earlier incarnation,  by any account, was not the eunuch he has become. The man could and did could write some incredibly sentimental and poignant songs including “The First Cut is the Deepest.” A lyrical poetry and empathy for all mankind is demonstrable in all his early works.

“Here Comes My Baby” is notable for its light, bopping sound that masks a broken heart resigned to ultimate failure. He has other songs just as good but none better.


Train in Vain - The Clash

Known for a driving punk sound and political songs like “White Riot” and “Washington Bullets,” the Clash wrote, to some, surprisingly bittersweet songs. There are none better in their repertoire than “Train in Vain.”

Musically  the song stays within the Clash’s definitive sound but the words are pure genius; strident and defiant but with a hint of longing. The songs asks the question what can expect from each other when in love.

It also answers it in no uncertain terms. No one really need clothes, a new car or a place to stay. Without someone to stand by you, no one can see it through. Then there’s only one option left.

And that’s a fact.


It Makes No Difference - The Band

Now, there’s no love as true as the love that dies untold. I wish I’d written that. This song is as plaintive as anything ever sung. Could be guy, could be girl, this song is universal in its appeal to every form of unfrequented love. The simple imagery of rain and no sun tells the whole story.

The Band (kudos, if you know why they’re called The Band) , in a remarkably short time period, wrote some ridiculously influential music that still resonates today. The songs on this are incredible but if you buy one album make it Music from Big Pink by Mrs. Danko, Helm, Robertson, Hudson and Manuel.


Dixie Chicken - Little Feat

Often recognized first for its chorus, this song’s lyrics are testament to the guy left behind and his subsequent epiphany. Every man is a little blind to the faults of his girl but this song uniquely captures the bittersweet ennui of one’s man’s realization that the girl he loved never deserved it.

The story told in this song by the incomparable Lowell George and his band mates takes us through the highs and lows of one poor guys seduction, marriage and subsequent betrayal by the love of his life. 

Still, the denouement when he meets “a bartender who says he knew her well,”  and the acknowledgement by the rest of the bar is priceless. Go ahead, try and find a better story of utter despondency and redemption told through song. I dare you.


Lola - The Kinks

Another song known for its twist ending, “Lola” is an amazingly constructed piece of bait and switch. Although not a movie, it was the “Sixth Sense” of its time in that no one forgets the first time they figure its out.

The relationship starts innocently enough over the treacly taste of champagne and devolves into a night of love and debauchery. The clues are there for the naïve but, in the end, passion and experience has its way.

Later, after all has been revealed, the protagonist of the song wonders what he lost if anything. A masterful bit of storytelling by the one of the most masterful songwriters of all time, Ray Davies, “Lola” is catchy, intriguing and finally revealing. It says as much about the listener as it does about the singer.