10 underrated songs with a story

“Mostly, I straddle reality and the imagination. My reality needs imagination like a bulb needs a socket. My imagination needs reality like a blind man needs a cane.”Tom Waits

A good song with a story stays with you. They weave their way into your psyche to such an extent that you go around spotting the Eleanor Rigbys of this world on public transport like a roleplaying game of Where’s Wally set in a failed society. These short stories captivate us and never get tiring with repeated listens—they are fables for the pop culture age.

Sometimes, they’re the best songs ever written. By nature, they are forced to swerve platitudes and offer up something new to the world of music. That unique nature renders them timeless. The stories are immortalised in song like folk tales of old, regardless of the genre.

While there are pedants out there who would claim that all songs tell a story in one way or another, these decidedly narrative tunes are the hardest to write. Rhymes need to fit neatly into a storied chronicle; the music must match the tone or else play with expectations in a meta manner, rendering the songs postmodern in a way.

This makes the tracks cherished additions to our dismal daily lives. However, perhaps by virtue of the fact that they demand extra attention and see diminishing radio plays as a result, there are some that fall into obscurity. Thus, we’ve raided the underrated realm to bring you a collection of gems from the storytelling genre.

10 underrated songs with a story:

‘The Strange Case of Frank Cash and the Morning Papers’ – T Bone Burnett

T Bone Burnett is the movie music maestro who has worked with the Coen brothers on a number of occasions, as well as being one of the most respected producers in music. This means he is no stranger to encountering a strange story and making it work.

The wild rolling melody of ‘The Strange Case of Frank Cash and the Morning Papers’ tells the story of a man who fortuitously happens upon a newspaper that is somehow being printed a day in advance. Naturally, he races to the sports results and makes a killing at the bookmakers, only for it all to go awry. And when things swirl out of control for Frank Cash, he takes a postmodernist turn akin to Kurt Vonnegut’s Breakfast of Champions, and Cash calls out the narrator, “this guy named T Bone Burnett, he’s been making all of this up”.

‘In Germany Before the War’ – Randy Newman

‘In Germany Before the War’ is an ominous masterpiece from Randy Newman. It’s one of the most unsettling and visual pieces of baroque pop music ever written. A track penned from the romanticised perspective of a child killer that plays out like a movie directed by Jennifer Kent, as it charters the grisly depths of Peter Kürten. Kürten’s nickname of The Vampire of Düsseldorf tells you everything you need to know about his blood-lusting modus operandi.

He attempted this hideous act on over 40 people, claiming the lives of at least nine between 1913 and 1929. Just to ram the point home, that’s 16 years of unapprehended neck-chomping! The master songsmith tells his tale as though it were a Peter Süskind novel, imbuing the darkness with poetry. Lyrics like “We lie beneath the autumn sky / My little golden girl and I / And she lies very still,” colour his crimes with a narrative, while the stirring melody and production flourishes add an eerie atmosphere like finely-tuned true crime prose.

If any one song crowns him the unreliable narrator, then it is surely this one. Empathy is vital to understanding, but you can’t really sidestep into the mindset of a man who races around clamping down on people’s collars. So, it is best to simply get the story straight from the vampire’s mouth and piece together reconciliations from there.

‘The Lady with the Braid’ – Dory Previn

It is a song that tells a familiar tale – the subtle art of gently cajoling a dinner date into a one-night stand. The nervous and frantic stream of consciousness moves from room to room and situation to situation with increasing desperation and perfectly observed fidelity to realism. “Would you care to stay awhile and save my life?” she quips, only to try and regain some composure by adding, “I don’t know what made me say that / I’ve got this funny sense of humour.”

The track is taken from the album Mythical Kings and Iguanas, which received critical praise and even relative commercial success upon release back in 1971 but seems to have faded somewhat into obscurity.

Aside from being a treat of utterly original and totally resonant lyricism, it is also a triumph of musical arrangement; the bassline waltzes us through the story, the delicate guitar picking adds the texture, while the meek but quietly dignified vocals perfectly play off the theme, and the soaring strings spare everyone’s blushes. Whilst Bowie may have been breaking new ground on what a song could be sung about, this offers an honest and original twist on a timeless tale of tortuous courtship.

‘Christmas Cards from a Hooker in Minneapolis’ – Tom Waits

In this masterpiece, Waits narrates a first-person letter from a prostitute to an ex. She writes of how she has fallen pregnant, cleaned herself up and is safe in a loving relationship with a noble track star trumpeter. Then, she slowly details how she still misses Charlie and thinks of him every time she drives by a gas station because of all the grease that slicked back his hair, revealing that all is not as it meets the eye. 

By the final verse, the story is revealed to be a fallacy as the prostitute from Minneapolis confesses that her story was a mere fable and that she is, in fact, incarcerated and in need of help. She signs her letter, “I’ll be eligible for parole come Valentine’s Day,” in perhaps the weirdest sexual proposition in music history. It is a measure of Waits’ mastery that amid this grisly tale of the sadly disenfranchised, there is something inexplicably festive that soars on the message that Christmas might not always be merry, but it offers up a sweet moment of reflection; nevertheless, even if you’re a delinquent in jail like Bernie Madoff.

‘The Man Who Couldn’t Cry’ – Loudon Wainwright III

As arguably the most underrated songwriter of the 1970s, Loudon Wainwright III mastered the art of character studies. Always laden with charm and a sense of depth, his best tracks are often comic tales of tragic souls judged without cynicism.

A case in point is ‘The Man Who Couldn’t Cry’— the story of a poor soul whose life falls apart after his dog got run over, his wife left him, he got sacked, lost an arm in the war, his creative attempts were laughed at, and then he was innocently sent to jail. All the while, he couldn’t cry. Then, one day, he was shipped to a home for the insensitive and insane. Therein, he cried for 40 days and 40 nights until he died of dehydration. If things sound dower, then the diegesis of heaven’s happy ending was always awaiting. From up in the firmament, he watches everything go his way. His creative works are now lauded, and he is reunited with his arm and his dog.  

It’s a tale that does what every Coen brothers movie has done to date—it braces the inevitable tragedy of life with the cushion of comedy that allows us to exuberantly laugh in spite of it. Sure, the film would be flecked with absurdity, but even the average Monday throws up madness that movies often neglect, and the Coen brothers could make us cry laughing about a man who couldn’t cry for sadness’s sake until the laughter of heaven’s grace welcomed him.

‘Small Car’ – Marvin Pontiac

Struggling to convince himself to create a record with vocals, the musician, painter, actor, director, and producer John Lurie decided to create an outsider artist character to serve as his conduit. His creation was called Marvin Pontiac, and the liner notes revealed his story: “[He] was hit and killed by a bus in June 1977, ending the life of one of the most enigmatic geniuses of modern music. He was born in 1932, the son of an African father from Mali and a white Jewish mother from New Rochelle, New York. The father’s original last name was Toure, but he changed it to Pontiac when the family moved to Detroit, believing it to be a conventional American name.”

In ‘Small Car’, his peculiar creation sings of a miniature race who drive around in cans and venture to the realm of giants in search of answers. What they find fills them with terror and wonder in equal measure, so they return home awed and satisfied that some meaning should remain out of reach. This adventure of a lifetime is then woven into the folklore of this tiny race forevermore—a tale of giants and the eternally unanswered question of why the stars keep shining.

‘Mr Charlie’ – Lightnin’ Hopkins

“Once in the country, there was this little boy, and he stuttered,” Lightnin Hopkins casually begins. It is a story of a pariah who left home after it became clear his mother couldn’t understand his stammering ways. Out on the road with a meagre flower pack full of possessions and a spiritual sack full of woes, he wandered his tired legs up to a dingy outbuilding called The Rolling Mill that belonged to Mr Charlie. The boy stammered his way towards Mr Charlie, asking if he had a place for him to stay. Mr Charlie told him he could stay in his Rolling Mill shack down the road so long as he saw to it that his stove never catches fire. The boy agrees, and Mr Charlie tells him he never wants to hear from him again unless there is ever a fire. One day, the boy is in the Rolling Mill, and the place catches aflame. He races his way up to Mr Charlie’s house to tell him about the blaze. As the boy struggles to spell out the problem in his failing words, when Mr Charlie stops him and says, “Look here boy, if you can’t talk it, then sing it,” at which point Lightnin’ Hopkins strums his guitar and bursts into song…

The twist here is a meta one because Charlie’s tale is actually the tortuous story of rock ‘n’ roll. His tale is one that forms an allegorical mirror to the tale of the blues. When those suffering on plantations couldn’t speak, they had to learn to sing. It is this encrypted meaning and the humanised expression of the blues that elucidated the vital necessity of music, both as a means of communication and as a soulful vessel to exultation.

‘The Bottomless Hole’ – The Handsome Family

Every child has tried to dig to Australia at one point or another, blissfully unaware that the pressure at the centre of the earth would squish them like a grape in Andre the Giant’s winery after his lunch break. Nevertheless, this ignorance is indicative of human’s inherent attraction to holes; financial holes, golf holes, arseholes (whether that be a bastard like Piers Morgan or a bearded wheeto), striking a match in front of an aeros-hole, and the most alluring of all: bottomless holes.

That’s the realm where The Handsome Family, a husband and wife duo based in Albuquerque, take you—a deep, dark pit at the bottom of the garden. With a country drawl, they beckon the listener down into this alluring pit with them, abseiling the abyss. What they are searching for remains a mystery; like most people who venture into unknown holes, curiosity has gotten the better of them, what they find is the folly of the human comedy: a misguided search for meaning in bottomless holes of nought.  

‘Two Lovers’ – Mary Wells

Plucked right from the reverb-laden era of the early 1960s when every song sounds like it’s just strolled out of the dentist, the woozy and sultry vibe of this twisted love triangle is a feast for the ears. However, beyond the swooning doo-wops, there is a surprise punch waiting at the end of this hook-riddled ditty.

This love triangle only has two sides—Mary Wells’ lover merely has a split personality. It’s not a mind-bending twist, but its brilliance is how it subverted the censors of the stuffy era. A woman with two lovers would’ve been heavily frowned upon by conservative radio stations and probably condemned to the ash heap of history, but the twist at the end saved it from this fate, even though you get the impression that Smokey Robinson wrote it with a wink and the twist is a red herring all along—it’s an anti-twist twist if you will.

‘San Francisco B.C.’ – Silver Jews

This loquacious comedy of new wave haircuts and lovers losing sight of the “things we quote ‘believe’” is a Bonnie & Clyde reworking in miniature by Silver Jews. Brimming with details and superb rhyming couplets like the unfurling punchlines to this verse: “Gene took off his hat and I noticed his hair / It was neatly trimmed, but a patch was bare / I knew it wasn’t new wave, it was human error,” it’s an epic exposé of acerbic wit riding the whims of a truly rhythmic song.

In a tale where the “cops couldn’t catch a bus” and kids sport “sarcastic haircuts”, there is an odd sense of heart and sincerity. Like the Martin McDonagh movie, the absurdity of this odious folly seems to be reflective of the wider human comedy that continually perpetuates itself via the unspooling trickle of minor tragedies. This is the story of fools ordaining their own unfortunate ends, as has always been the case in San Francisco and every metropolis since B.C. and possibly before.

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