Thursday, September 30, 2021

The Saddest Singer on Earth: Amy Winehouse and The Blues

Introduction:  Welcome to My World

“When I’m singing, I’m happy. I’m doing what I can do, and this is my contribution to life . . .”
– Anita O’Day (an early incarnation of Amy)

Incredibly enough, Amy Winehouse passed away ten years ago this summer. But this is a story about her sad music and the sad music that inspired it, not a story about her problems or the flaws that caused them. Born September 14, 1983 and died July 23, 2011. That’s her biography, plain and simple. Her own autobiography, however, is mostly embedded in her two releases while still vibrantly alive and brazenly sashaying, her debutante surprise Frank in 2003 and her surprisingly mature masterpiece Back to Black in 2006, and that autobiography is considerably more complicated than her actual personal history. They are the light and the dark sides of both her real character and her chosen edgy persona, as well as of her deeply impressive musical artistry, the first one inspired by her love of Sinatra (or rather his ring a ding-ding Rat Pack spirit), the second one inspired by her love of oblivion (or rather by its lack of awareness).

Her story is also about sadness in general and how music can alleviate it in particular. The perplexing beauty of her genre-bending style is evidence that her Back to Black recording achievement absolutely transcended all the many styles and sensibilities it stirred together and became what I would call quintessential pop music, music for ears belonging to a drastically eclectic and diverse listening audience. She clearly invented a hybrid form of her own imagininge that heated up and melted down seamlessly the varied inspirations she inherited and encountered along her own hyper-accelerated passage to pop stardom. Pop music needs to be taken as seriously as it deserves to be as an important art, so defining what makes something great pop music is the logical place to begin.

Torchy Ella Fitgerald in 1947 when roughly the same age as her inheritor. (Photo: Wikicommons)

Was Amy Winehouse a pop genius? Probably, but not of the garden variety we’re more  familiar with such as Madonna or Lady Gaga, and more like the primitive kind modeled by the late John Lennon or Brian Jones. I’m not comparing their music; that would be folly. But I am comparing the rough, untutored, alien brilliance of how they did what they did without even their knowing how to do it. Such artists are driven to do it, despite their shyness, their neuroses, their complexes, their fears, their insecurities, driven to do it the way a wild animal tries to escape from a celebrity trap that it stepped into of its own volition. Amy was the same kind of pop genius as Billie Holiday, Ella Fitgerald, Julie Wilson, Peggy Lee or Anita O’Day, and while it’s true that those names are most often associated with the jazz idiom, they were all superb blues artists who became well known enough to cross over into pop. And Winehouse was perhaps one of the most surprisingly gifted blues musicians to come along in ages. Though she definitely shared a bluesy swing vibe with both Nina Simone and Sarah Vaughan, as well as a raunchy in your face self-exposure similar to Janis Joplin and Laura Nyro, she seemed to occupy an outlier status separate from all of them.

She was also a naturally raw and consummate burlesque performer by instinct and intuition if not by temperament, and one who would deftly use the art form of the music video as an amazingly fertile device to seduce and satisfy the audience that loved to watch her suffer through her own version of the Fado torch song. We all simply adored watching her sultry strut, strutting as only she could strut, whether on stage in performance or on video, in recordings or even sauntering down the street trying to escape her shadow. It wasn’t a wild strut like that used by Tina Turner when she asked what love had to do with it, or of Aretha demanding “Respect”; it was more the strut of an exotic bird somehow confusing confidence and fear at the same time and short-circuiting our expectations through a combination of subtle raunch and permanently delayed gratification: the ultimate pop weapon. It was a weapon which would be loaded with heartbreaking and beautiful ammunition and aimed at the musical world in an audaciously brave yet tenderly vulnerable way in Back to Black, a weapon the listening audience wanted to see her shoot, again and again and again, until she finally ran out of ammunition.

Anita O’Day, 1958, A classic torch-song queen who also struggled with substances. (Photo: Shorpy)

By definition, then, pop music is probably something without a precise definition, since we never quite know just who or what is going to strike a huge public chord, but we can certainly identify a range of ingredients that inform its style: the singer-songwriters who most inspired Back to Black may have had different syles of delivery but they all shared a single obsession with being real, and being honest. Eschewing artifice, and often even poetry, in favor of raw truth on its own terms, they often created a whole new kind of poetry. And Winehouse studied them often and well, and though she may have been a disruptive student in class she did her homework,  preparing for the masterpiece she left behind for us shimmering in history.

If the pop song has evolved into the personal and public soundtrack for the last century, as it so clearly seems to have done, what does that tell us about the emotional movie we all live in? In her brief career we were given the gift of her remarkable music in a hyper-personal and confessional way seldom seen or heard before. Joni Mitchell’s brilliant album Blue or Marianne Faithfull’s searing Broken English come to mind, although both of them were skillful survivors. Amy’s was a painful gift, one that – luckily for the rest of us, sitting comfortably at home far away from her talented but troubled fray – just keeps on giving us listening rewards a swift decade and a half later. Winehouse was a Dusty Springfield drenched in darkness, she was Petula Clark from hell, who, instead of taking us all chirpily downtown, took us all down there, lá-bas, where she seemed to spend so much of her short, sad life.

But it’s always important to dismantle a mythology to see what lies at the bottom of it, assuming the figure being mythologized stands at the top. One of the best ways to do this is to try and focus as much as possible on the artworks the artist actually made, and that is the critical intention of this article, so we have to at least attempt to find some kind of borderline between personal pain and musical brilliance. In the end she still somehow able to artfully communicate richly human documents to the rest of us. We just called it entertainment.

Island Records, 2003 (Island).

After all, surely we all have to feel somewhat guilty when a gifted singer such as Winehouse writes a song like “Rehab,” the opening salvo from Back to Black, and we all chime in chorus along with her, “No no no,” instead of what we should have been saying, “Go go go.” Though clearly it was her family, ex-lovers, managers, and agents who should have been intervening, not us, since we were only the guilty beneficiaries of her inspired bedlam. We were perhaps understandably distracted by her high-spirited defiance, even if her rage to live took her away at the horribly popular age of 27. Like all of those other members of that sad club, she was what the poet Pope called a wise fool, a medium who spent her short life at the threshold of the known and unknown, and she left behind only two albums: the first a youthful, healthy and bouncy breakthrough jazz-flavored record, the second that dark and soul-blistering pile of steaming sad brilliance called Back to Black, the masterpiece for which she is rightly remembered with some reverence. 

Back to Black is a documentary movie for our ears because it paints moving pictures of hyper-personal feelings and experiences, just as Dylan does so well, in a manner so image-evocative that the songs are virtually perfect for the persona-rich video medium that was used so effectively to visually promote them. The excellent video for the song “Rehab,” for example, or the even more excellent video for the album’s title song for another, both work so effectively because the songs themselves are already cinematic epics. A song such as the harrowing “Love Is a Losing Game,” for instance, feels like her own Gone with the Wind, but compressed like carbon into a diamond for a mere two minutes and thirty-five seconds. Like the ratio of dog years to human years, in the shimmering world of pop music a decade feels like an eternity. Now is perhaps an ideal time to listen again, probably to cry again, and most importantly, perhaps, to remember just how huge a creative shadow her brief presence has cast across our popular culture.

Why is the Back to Black album from 2006 so important?  Why does it deserve to be called her only masterpiece and cherished? So far there are more than 20 million reasons worldwide. Each one represents a human being from a diverse culture who owns a copy and for whom it has some special personal meaning. It therefore has over 20 million meanings, each one being the true and correct one. After the fifteen years since it was dropped from the sky by a strange and exotic bird flying high overhead, for each listener it has come to symbolize a heartfelt message about the human condition composed especially for them, a message that transcends cultural boundaries and is recognized as that rare and unique work of art which is destined to withstand the test of time. In other words, it is a classic. Some of her special value as a popular culture figure is also, of course, reflected in other tangible forms of recognition such as multiple awards from the music industry. She may well have been a savant; only time would have told, and time, as jazz giant Artie Shaw once astutely remarked, is all we’ve got.

Once something so personal transcends the private realm and breaks through to the universal realm, it gets to be regarded as a classic. A classic is any work of art, whether it is a painting, a book, a film or a musical composition, that instantly makes the viewer, reader or listener feel that the work in question was painted, written or composed for them personally, and it remains permanently situated in the present moment, no matter how much time passes since its initial encounter in the cultural arena. A classic piece of music is not necessarily one that is classical, but rather one that transcends the time in which it was produced, influences everything that follows it and has a shared meaning long afterwards. But in the end, the more compelling reasons for Back to Black’s privileged position in music history are these even more basic ones: how it was composed, how it was produced, how it was recorded, how it was performed live, and perhaps most importantly, how it sounds.

All these years later it still sounds like a predestined marriage between heaven and hell, a combined technical production achievement and poetic musical accomplishment that remains uniquely aloof and untouchable. In a strangely alluring way, there’s everyone else in pop music, and then there’s Amy Winehouse. But perhaps the secret key to the door of her music, or at least one of them, is to firmly place her in the context of the torch song tradition. That way she doesn’t rattle around quite so much in the historical wind and she also appears far less alien and strange than at first glance and hearing. Winehouse didn’t exactly come out of nowhere. It only seemed that way. But she was just the latest model of a storytelling vehicle that has a long established history, though she managed to mash together several idioms in fresh and new way that elevated all of them while vastly extending their reach to a huge global pop audience.

While the blues form she alchemized (along with jazz, rap, reggae, ska and girl group rock and roll) was an African American invention, there are many examples in all human cultures, some of them quite ancient, of songs of lament. Blues singers are the grimy artistic canaries that we all use to lower down into the emotional mineshaft, in order to signal safety, danger or loss in our own lives through these emblematic mournful songs of theirs, raised on musical ropes back up the surface where the rest of us live in comparative comfort and utlize their existential experiences for our amusement. Few did it quite as exquisitely as Winehouse. That might perhaps tell us as much about us and our voyeuristic schadenfruede as it does about her.

How on earth did someone as young as Amy manage to make grief on steroids sound so incredibly beautiful? Apart from Winehouse’s own remarkable voice, her visceral response to music and her uncanny sense of timing and coordination, the question leads us to the inherent artistry of the producer’s integral role in the transformation of feelings into form: the genius of Mark Ronson and Salaam Remi. So then, let’s consider this memorial article: Back to Winehouse/The Album as Artifact, as a kind of a means of reorienting ourselves to what she accomplished against all her odds. Maybe a decade and a half later is perhaps an ideal time for remembering her scintillating songs from the heart, one broken on her own private romantic wheel but made public in a most disconcerting manner. 

Winehouse in her “prime".

“My name is Might-have-been; I am also called No-More, Too-late, and Farewell."
– Dante Gabriel Rossetti

Back to Black/Creative Credits:

Featuring Amy Winehouse and The Dap-Kings
Produced by Mark Ronson and Salaam Remi
Design: Alex Hutchinson 
Management: Raye Cosbert
Photography by: Alex Lake, Harry Benson, Mischa Richter / Cover Photograph: Bryan Adams

Back to Black was released by Island Records on October 27, 2006. It has sold over 20 million copies worldwide, and was awarded five Grammys in 2008: Record of the Year, Song of the Year, Best Pop Vocal Album of the Year, Best New Artist of the Year, and Producer of the Year. Winehouse became only the fifth female solo artist to receive five recording awards in one night.

Most revealing is her conclusion: “And it’s not just my pride / It’s just till these tears have dried,” suggesting that all her troubles were only temporary and just a response to her heartache, which would, she assumed, have to end sooner or later. Wouldn’t they?

“You Know I’m No Good”:
Clearly identifying herself as a young woman with self-esteem issues, and not afraid to confront them, at least in her art, she declaims with an ironic sort of pride, “I cheated myself, like I knew I would / I told you I was trouble, you know that I’m no good.” Far from being a classic break-up song about a partner who cheated on her with someone else, this tune magnifies the fact that she has cheated on herself, a troubled twist on the classic torch song take, and one of the reasons the public related so deeply to her turmoil.

“Me and Mr. Jones":
“Nobody stands between me and my man, / It’s me and Mr. Jones” repeats the sentiment that not all of her relationships are or have to be of a romantic or physical nature. Naturally she fights with him as much as she would fight with a lover, but in the end her allegiance is to friendship over love, at least for as long as this bouncy tune unfolds.

“Just Friends”:
A core lament that a lover can never be a friend, or at least not the lovers she seems to pick, or the ones that seemed to pick her. Again she references her lover’s competing partner, the one who has taken or is taking him away from her: “When will we get the time to be just friends? / I’m not ashamed but the guilt will kill you, if she don’t.”

“Back to Black”:
The ultimate Phil Spector girl-band tribute, which channels The Supremes in a marvelous way without at all appearing to be copying, and another example of how her gift for fusing styles was authentic and sincere rather than aping or plagiarizing. She is also all three Ronettes, all three Dixie Cups and all three Shirelles merged into a monument to infidelity and its ramifications.

And we all get to listen in on the whole affair. Torch songs have never before reached either this level of intensity or intimacy. It’s hard to imagine they ever will again.

“Love is a Losing Game":
Never has a personal destiny, actually in the hands of a lover the whole time, been cast in so inevitable a shape, so pre-destined that all hope is abandoned. But its abandonment is also sculpted, through time, music and performance, into yet another sonic monument to giving in, giving up, and going on. While we secretly listen in the other room, our ears pressed to the walls that are closing in around her.

“Tears Dry On Their Own
My personal favorite among all of Winehouse’s great anthems. A simple but powerful message: “I don’t understand, why do I stress a man / When there’s so many bigger things at hand?” In a sudden moment of rare clarity she even admits that it’s her own responsibility and that he didn’t owe anything to her, but still she had no capacity to walk away. If only that were the case. Instead we’re left with a perpetual refrain, sung with incredible charm, “He walks away, the sun goes down, / He takes the day, but I’m grown / . . . My tears dry on their own.” But unfortunately there are always more where they came from.

“Wake Up Alone”:
Dread soaked in soul is the best way to characterize her breathtaking music, which has to be heard to be understood. It’s kind of the Finnegans Wake of soul music in that respect: reading the lyrics tells you nothing; hearing them float over the magic beat of The Dap Kings tells you everything you’ll ever want to know about the ambivalence of avant-garde romance.

“Some Unholy War":
She asks an intriguing question about putting it all in writing: who is she writing for in the end? Just the two of them alone, with her “reciting her stomach standing still” . . . it’s like we’re all reading her will. But she will battle on until the bitter finale, “just me, my dignity and this guitar case”? Eventually the song detours to announce that her man was in fact fighting some unholy war, but alas, that war was the one going on between them, a nation of two.

“He Can Only Hold Her”:
A simple song, an ambiguous song, disguised by the customary brilliance of the instrumental and the singer’s gift for an arresting melody riding on a wave of stunning rhythm. In a sense, this one is the essence of what rhythm and blues is all about: a deep sadness seeking to find solace in the arms of accelerated emotions.

The point here is that scintillating talent often arrives early, matures young and flickers out too soon. Almost all the best singer-songwriters in the modern tradition reached a breathtaking peak of talent at almost precisely the same age of 24. Who knows what that means or what it reveals about talented young hearts? As desirable as it may be to divorce her status as a demonic diva from the glorious music she created, it is implicitly difficult to avoid something which is so inherent to the success of one and the doom of the other. For Amy Winehouse, there was no safe place, and that’s what she wrote about. For her, one was company and two was a crowd, and that’s what she wrote about. She was an exemplary storyteller, but her stories were not invented. They didn’t emerge from a shimmering fictional place like Chekhov or Hemingway stories, for example; instead they rose to the surface of a self-actualized and emotionally swampy place, from her own personal experiences in love and life, loss and longing. This too was not exactly new, but nobody else ever did it quite like she did.

It was precisely this degree of almost unbearable self-revelation and honesty that seemed to click with a worldwide listening audience, perhaps one tired of polish and perfection in the pop music industry at the time. Being as shy and obviously self-deprecating as she clearly was, she must have been stunned and a little taken aback by the nearly universal critical acclaim heaped on her, a bonus on top of the already massive popular appeal she had with everyday listeners and lovers of the multiple genres she and her new Svengalis had mashed so perfectly together.

This also, of course, tells us something important and possibly disturbing about the times in which we live.

The intricate fabric of isolation, loneliness and self-absorption, the consequences of merging private and public life, the wildy unconventional, exotic and often raw vocal styles of Back to Black manage to speak to all of us collectively and to actually communicate what we ourselves are feeling. A certain emotional wavelength is superimposed upon all the best pop songs, at least the ones that rise to the condition of works of art, regardless of their stylistic differences, and this is especially the case when stretched across the tightly-wound skin of the best torch-songs. Back to Black, her only masterpiece, had them aplenty, seamlessly collaged together from almost ten different musical styles and traditions. That’s why it will be remembered and played again and again, as long as there are broken or wounded hearts in the world who need its soothing bandages, and as long as music lovers wonder at the mutant heart of music itself.

The subtextual message I hope the reader of this essay takes away in response is two-fold: first, an astonished appreciation for her innate and inborn musical skills, skills that were so instinctual that they couldn’t ever be learned and barely even be practiced; and second, a deep sense of loss over the fact that even her towering creativity couldn’t save her from herself, at least enough to enable her to make more music, the thing she loved to do more than anything else in life. Back to Black provided, and still provides in the fifteen years since it dropped, a fragile building made of breath, a place both safe and dangerous at the same time, a breathturn where our confused and confusing popular culture could take up residence, at least for the duration of a song. How she was able to deliver this architectural feat so skillfully is still a little baffling, at least until we realize a crucial fact about the often disturbing poetry of popular culture.

And that is this, which Proust pointed out:

The men and women who produce works of genius are not always those who live in the most sophisticated or delicate atmospheres, not those whose conversational style is the most intelligent, or whose personal cultural experience is the most extensive, but rather it is those who have had the ability, even the power, to suddenly cease living only for themselves and to somehow transform their personalities into a mirror.

It’s a cracked mirror but it’s also one into which we can all gaze forever. For my part, what I most personally regret, and even almost resent, is the sad the fact that there won’t be any more Winehouse records of this breathtaking caliber to keep us company in the dark night of the soul. Admittedly selfish on my part, but I feel I have to paraphrase that consummate pop surivor, Iggy Pop, when he barked out “I want more!”

I wanted more Amy music, I’m not going to get any, and that just isn’t fair at all. 

Donald Brackett is a Vancouver-based popular culture journalist and curator who writes about music, art and films. He has been the Executive Director of both the Professional Art Dealers Association of Canada and The Ontario Association of Art Galleries. He is the author of the recent book Back to Black: Amy Winehouse’s Only Masterpiece (Backbeat Books, 2016). In addition to numerous essays, articles and radio broadcasts, he is also the author of two books on creative collaboration in pop music: Fleetwood Mac: 40 Years of Creative Chaos2007, and Dark Mirror: The Pathology of the Singer-Songwriter, 2008, as well as the biographies Long Slow Train: The Soul Music of Sharon Jones and The Dap-Kings2018, and Tumult!: The Incredible Life and Music of Tina Turner2020. His latest work in progress is a new book on the life and art of the enigmatic Yoko Ono, due out in early 2022.


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