Shameless, Seductive and Sincere: 20 Years of Amy Winehouse’s Frank

Winehouse's debut album is the closest we’ll ever get to knowing what she was like before fame, before her death became greater than her life.

Music Features Amy Winehouse
Shameless, Seductive and Sincere: 20 Years of Amy Winehouse’s Frank

I don’t want to watch Amy Winehouse die again. Whether intended as a revisionist reappraisal or a lesson on the consequences of sex, drugs and rock ‘n’ roll, Winehouse’s premature and tragic demise has perpetually been rebroadcast and commercialized since her actual death in 2011. With the Oscar-winning success of the 2015 documentary Amy, producers decided to just do it again and again and again. Now, a forthcoming biopic, Back To Black, is set to be released sometime in 2024. She could die a thousand times, but would her story ever really change?

This retrospective canonizing is a symptom of being an ever-so-fascinating Dead Girl. Think Princess Diana—who also got her very own biopic just two years ago—or Frida Kahlo and Billie Holiday. It’s a phenomenon that Edgar Allen Poe once described as “unquestionably the most poetic subject in the world,” as it eulogizes—and inflates—the helplessness of a girl who “could’ve been saved.” All these documentary retellings, exhibitions inside her thrifted closet or deep-dives into adolescent journals are to identify pieces of the greater “what went wrong” Dead Girl puzzle. In this corner is a bad childhood, in the middle a predisposition to alcoholism. But, no matter how many pieces you connect, the picture will never fully match the one on the actual box. So we disassemble truths in an attempt to create a sanctifying image but, in actuality, we create an artifice where women are their tragedy. Or maybe a Halloween costume.

The “real” Amy Winehouse is not that hard to find. Before the drunken lament of Back to Black—before the beehive hairdo and the thick, winged eyeliner reaching all the way back to her temples and before the U.S. even really caught wind of her—Winehouse released her 2003 debut Frank via Island Records. It’s the most literal exposition to her story, as she “wouldn’t write anything unless it was directly personal to [her] because [she] wouldn’t have done it right,” Instead of watching some Hollywood bigwig’s translation, you can listen to her unfiltered memoir. Like a flashback in a movie, Frank paints a sunny picture. Winehouse is 19 with long, combed hair, a wide smile and full cheeks. Both she and the music are less complicated, less jaded. It’s the closest we’ll ever get to knowing what Winehouse was like before fame and it’s been here all along, for 20 whole years—and it begins with a scat.

Now introducing: Amy Winehouse, the jazz singer. Undeniably one of the most recognizable voices of the last century, Winehouse’s North London drawl allowed her to effortlessly curl her syllables, coating them in a rich and smokey glaze—or a short, sharp tang, as if spitting them out. Her contralto range, the lowest female register, sounds as if her notes are hanging in the air: long, vibrating and wretched. This is not unlike the jazz vocalists she grew up listening to, such as Sarah Vaughn and Dinah Washington. She makes these influences known as she samples Ella Fitzgerald’s “Lullaby For Birdland” for “October Song” and covers George Benson’s “Moody’s Mood For Love,” as well as Billie Holiday’s “(There Is) No Greater Love.” According to Questlove, she could “school you in jazz” and her knowledge and reverence is woven throughout each of the 15 tracks found on Frank.

In fact, there are four distinct “Amy trademarks” found on Frank: walking bass, sweet jazz chords, hip-hop beats and a ride cymbal. Akin to the neo-soul fusion of Erykah Badu, Winehouse revives the traditional swoon of a jazz crooner by pumping the heart of her tracks with the swaggering beat of a rap instrumental. In fact, almost all the music on Frank came from live instrumentation with production from Salaam Rami—known for his work with the Fugees—who she’d return to for Back To Black alongside a relatively unknown producer at the time, Mark Ronson.

Most songs on Frank only have a couple moving parts, as Winehouse’s voice is at the center—directing the melody and narrating the story. After the scat intro, a steady beat picks up, accompanied by sweet, sparse guitar chords for “Stronger Than Me.” Although lauded with the Ivor Novello Songwriting Award, to modern ears “Stronger Than Me” is blatantly transgressive. Winehouse is mad at her man for not “living up to his [gender] role,” calling him a “lady boy” because he always wants to talk and be comforted. She even bluntly asks: “Are you gay?” Whether or not she really believed male sensitivity is exclusively linked to homosexuality, the song is quintessential Winehouse: lyrically edgy, but unflinchingly sincere. It’s also indicative of the kind of fiery romance she finds thrilling, famously proven true with her explosive and tumultuous relationship with ex-husband Blake Fielder-Civil, the impetus to her follow-up Back To Black.

By nature of her shameless, occasionally ill-mannered tongue, Winehouse is both a natural raconteur and a provocateur. Sometimes her pithy mouth gets her in trouble, but it also gets her a half-million-pound record deal. This isn’t so unlike the namesake of the album, Frank Sinatra. His voice is universally beloved, but the man himself was, as Amy put it, “an arsehole.” And Winehouse also has no problem being an arsehole. Her callousness lends itself wonderfully to quippy hooks and verses. “Fuck Me Pumps” is one of those arsehole tracks, as she satirises the promiscuous, gold-digging party-girls found at the bars every night. It’s full of zingers: She notes how the women “all look the same,” and can’t “sit down because their jeans are too tight.” They’re all “pushing 30 and their tricks no longer work” and their dream is to just be a “footballer’s wife.” She finds them pathetic, much like the man on “Stronger Than Me,” but recognizes that without these pitiful women there “would be no nightlife.”

But she is not above self-criticism; she can point the finger back at herself with the same extremity, if not more so. On “Amy, Amy, Amy,” she recounts a (true) illicit relationship with her Diesel jeans-wearing science teacher. She walks past his desk in heels just to “show him how it feels,” admitting her “weakness for the other sex” causes her to fantasize and distract her from her writing. In between the seductive verses, you can hear her scolding herself. “Amy, Amy, Amy” she sings like the shaking of the head. But those voices are still not as strong as her carnal whims. This overpowering sexual impulse is something she reckons with all throughout Frank. It’s her deadliest weapon, but it’s double-sided; it punctures her too.

On “I Heard Love Is Blind” Winehouse is trying to convince her boyfriend to forgive her for sleeping with someone else—who just so happened to look exactly like her boyfriend. It’s not cheating, she insists, “you were on my mind” and she thought of him “as she came.” It’s his fault, she argues (we might call this gaslighting), because he left her alone and “she was lonely.” On “In My Bed” she sleeps with the wrong person, yet again, but this time it’s her ex. Singing over the aggressive breakbeat from Nas’ “Made You Look,” also produced by Rami, she tries to tell the man not to confuse emotions with sex. He’s just for pleasure, Winehouse admits, because “the only time I hold your hand is to get the angle right.” Eventually, her partner has had enough of her antics and, on “Take The Box,” she discards the “Moschino bra” she was gifted and returns all mementos back to her lover after the dissolution of their relationship.

About midway through the album, Amy wonders why she keeps making the same mistakes. Where do these destructive impulses come from? Why, she asks on “What It Is About Men,” does she take “the wrong man as naturally as she sings?” This is arguably the most fearful Winehouse gets on Frank. She’s terrified that, perhaps, her father’s infidelity might have left her without faith forever. She often subsumes the “male” construct of using others for sex and disregarding her partners’ feelings. Perhaps, she hypothesizes, this romantic destruction is genetic. Maybe her sexual compulsions are just her “demonstrating her Freudian fate.” Like usual, she’s only sort-of-joking, but behind the smirk is the true experience of a young girl just trying to figure herself out. In all, Frank is that very investigation, and it’s exciting to be able to do alongside her.

Right before the release of Frank, Amy was asked how big she thinks she’s going to be. “I don’t think I’m going to be at all famous,” she responds. “I don’t think I could handle it. I’d probably go mad.” Just for a moment, she was right; she wasn’t that famous. Only four months after Frank’s release did it peak at #13 on the UK album chart. It wouldn’t be released in the US until 2007, after Back To Black’s global success—after lead single “Rehab” thrusted her into the spotlight. Although earning her three Grammys, “Rehab” found Winehouse introducing herself to the world as if to say, “Hi, I’m Amy. I’m an alcoholic.” Because of this, she was right again. She really couldn’t handle it.

Winehouse’s success grew in tandem with her addiction, as well as the rise of celebrity gossip magazines and websites. Paparazzi would park outside of her house, drooling over themselves for a compromising picture. You couldn’t walk into a CVS or a grocery store and avoid the bold yellow lettering documenting every step of her destruction: Back to Beehive as Wino drinks until 4 AM, read a Daily Mail cover. Amy’s drunk face doesn’t surprise us anymore. For Winehouse, the limelight was luminous and all her blood, sweat and tears were extracted and served to the masses as a mere joke. Like Britney Spears’ public meltdowns, or Kim Kardashian and Paris Hilton’s sex tapes, there seemed to be nothing juicier than a woman acting unladylike. And even before her addiction, like on Frank, Winehouse was unladylike—she says so right off the bat on “Stronger Than Me.” She was immodest and raunchy, often pushing the limit of who a woman is supposed to be and how a female artist is supposed to talk and act. And because she was this way, she was punished. When writing, Winehouse said she wouldn’t let her songs just be sad, they needed a punchline. So the world didn’t frame her as sad at all. They treated her without empathy and instead turned her into one of her songs: a punchline.

Perhaps this is why so many producers and outlets cannot stop regurgitating the “tragic story of Amy Winehouse.” More so than people wanting to get to know the tragic Dead Girl, they want to absolve themselves of their complicity—or even attempt to erase what really happened. To me, that’s why Frank is so important: It tells you the story of a rebellious girl infatuated with love and navigating her relationship to sex. Frank tells you exactly who Amy was before the world had a chance to change her story.

If Amy Winehouse had lived, perhaps she would’ve pulled herself together and retreated back into the slums of Camden to sing at small, smokey jazz clubs—which was really what she enjoyed most. Or, she would’ve joined the jazz/rap group supergroup she’d been planning with Questlove, Yasiin Bey and Raphael Saadiq. It’s hard to say what would’ve happened and how much could’ve changed if the world had been more forgiving and, really, less cruel.

Amy Winehouse is so precious because there is no neat bow to wrap around her career; there is an open casket. So she probably will die again, almost certainly in her upcoming biopic. But what will never die is her music. Adele was quoted saying Frank “changed her life.” Lady Gaga tweeted that she knew “there was hope” because of Amy Winehouse. So, instead of bringing her back to life just to kill her all over again, maybe we should close her casket and let her rest. Instead, we can put her legacy into something like a jewelry box. Perched in the middle is a figurine of that rebellious North London teen with a beer in her hand and a cigarette in her mouth. And when you open the box you can hear her singing, singing, singing her one-of-a-kind sound.

Sam Small is a freelance writer of sorts & shorts based in Brooklyn, NY. She has written for NME, Consequence of Sound, Clash Magazine and Under The Radar.

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