Making a Case for Amy Winehouse as a Jazz Singer

I celebrate her legacy, and imagine what Amy Winehouse might have done if she hadn't died at age 27

A few months back, I posted some video clips of Amy Winehouse on Twitter, and got a little pushback from the jazz police—those vigilant fans who protect the genre against the taint of anything impure, especially if it makes money and reaches a large mass audience.

“You write about a lot of musicians far greater than her. What’s the hype all about with this one?” asked one Tweeter. Fair enough. But after thinking a while about how to respond, all I could offer was: “That would take more than a tweet to answer. I probably should find time to write an essay on her work—I’ll put that on my ‘to do’ list.”

But I was happy to see Jason Marsalis take the plunge and reply to the same comment: “[Amy Winehouse] was one of the few mainstream artists in her generation that knew music while the majority of other mainstream artists didn’t have a clue.”

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My thinking is pretty much along the same lines as Jason’s. But this is a subject that deserves more in-depth consideration, especially now that Winehouse isn’t around to make a case for herself.

The above exchange happened on the day after Winehouse’s birthday (September 14), but she didn’t get the chance to celebrate many of them. Like so many music stars, she died at age 27—they even call it “The 27 Club,” and that’s one all-star group you definitely don’t want to join. Since that exchange six months ago, I’ve been mulling over how to write an essay on this singer. At first I thought I would do something similar to my recent piece on the final days of Billie Holiday—so I got a stack of books on Amy, and started reading about the circumstances leading to her death at age 27.

Frankly, this was just too painful. Too much music writing focuses on the sordid details of our fallen heroes—when, in fact, we’re all fallen. It’s only a matter of degree, and many of us are fortunate we didn’t make worse decisions at age 27.

In the case of Billie Holiday, I thought it worthwhile showing how the harassment of legal authorities and the indifference of medical professionals contributed to her death. But in the case of Amy Winehouse, the morality play at work in her life is more ambiguous, and it’s all too easy to blame the victim. I’m reminded of one of my favorite cinema exchanges, from Clint Eastwood’s Unforgiven.

Kid: “I guess he had it coming.”
Clint Eastwood: “We all have it coming.”

That pretty much sums up my philosophy on those matters.

So I decided to focus on Winehouse’s music instead, but really I want to look just at her jazz singing. Because this is what turned me into an Amy Winehouse fan. I didn’t pay much attention to her pop music until I first heard her rendition of a jazz song, which forced me to reconsider everything I had assumed about her.

I’ve heard many rock and pop stars tackle jazz songs over the years, and the results are usually ho-hum—sure, they can hit the notes and strut around the stage with a flashy demeanor, but their phrasing just isn’t right. I can’t really blame them—these superstars have been performing in huge arenas and stadiums, where they need to project enormous power and intensity into every lyric. They need to reach the music fan sitting in the back row of the stadium, a hundred yards away or more, and that requires a turbocharged delivery few of us commoners in the kingdom of music can even imagine. So it would be genuinely surprising if they could turnaround and sing the jazz repertoire with the nuance, flexibility, and care over each syllable and word that this music requires.

Jazz singing is often oblique. You get to the emotion, but it’s not a straight line. The phrases don’t sit evenly on the beat (or even unevenly), but flow on top of it in a way that defies precise mathematical definition. I once worked with an expert on measuring the micro-shifts in rhythmic placement in a swinging beat, and it was sobering to learn how a way of phrasing that sounds completely relaxed and conversational involves the most complicated relationship to the ground beat.

Singers who have developed their skills singing stadium rock or Broadway shows or slick commercial pop actually have a disadvantage—they need to unlearn much of what they have learned if they hope to get into the essence of jazz. Years ago, I had several surprising situations playing piano for opera singers who wanted to ‘do jazz’—and was stunned to discover that these vocalists, with so much training and performance experience, couldn’t loosen up. That was how I described it to myself. If they could just relax a little, or so I assumed, they would have no problem.

I eventually came to realize that this blockage had nothing to do with relaxation or loosening up. It was simply a matter of genre. They had risen in a field which required a metrically rigorous approach to rhythm and phrasing, and those rules just don’t apply to jazz. You might even say that they undermined the key elements of the jazz experience. Rock or pop stars also have their rules—although we like to believe (erroneously) that their music is just some unleashed emotional current unfettered by specifications and regulations—and it’s a rare singer who can make the leap to jazz.

Here’s a curious observation: I have heard some rockers do an amazing job of singing jazz, but they are almost always obscure or failed artists. Because of their lack of commercial success, they pursued their rock careers in small clubs, not big arenas, and this taught them things about intimacy and emotional vulnerability onstage that megastars never have a chance to learn.

All this is a way of saying that I was shocked when I heard how well Amy Winehouse handled the microtonal shifts and oblique rhythmic demands of jazz singing.

Let me share a couple of examples. Here’s a duet with Tony Bennett, recorded shortly before her death.

She actually reminds me of Billie Holiday here—and I don’t hand out compliments like that glibly. Actually, I pretty much never hand out compliments like that. But listen—and especially compare where her vocal sits in comparison with the stated beat and the written melody—and make up your own mind. To be blunt, Tony Bennett (full disclosure: one of my heroes) is more guilty of over-singing here than Amy Winehouse. What a remarkable admission that is.

Here is a video of Winehouse singing one of her own compositions. This has a strong R&B tinge, but those same jazz vocal elements are evident. “Stronger Than Me” enjoyed a short stay in the top 100 in Britain, and never charted in the US, but this is an impressive performance by any measure.

Winehouse certainly had technique to spare. She could bend notes with total control, but also hit them cleanly when the context requires it. Consider the ease with which she navigates through the complexity of this pop-oriented version of the bop vocalese song “Moody’ Mood for Love”—wickedly intricate but evoking no sign of strain. I don’t always dig the accompaniment, as on this oom-pah version of “Our Day Will Come,” but her singing of jazz standards is real and vital, and perhaps all the more striking when the band is dishing out so many cliches. And check out what she can do with more understated support, as on this George Gershwin standard. The YouTube listing describes this is an Ella Fitzgerald cover, but I’m especially impressed by her sassiness at the 3:30 mark, where Winehouse digs into a Dinah Washington bag, and with complete authority.

How does she do it? I might have guessed it, or probably already should have known it. But Winehouse, as I learned, had very deep jazz roots long before she became a star.

Her paternal grandmother was a singer who had dated Ronnie Scott, for heaven’s sake—Amy got her granny’s name “Cynthia” tattooed on her arm. Amy’s mother Janis was a chemist, but with two uncles who had worked professionally as jazz musicians, and a mother who also had aspired to be a jazz singer.

Her father Mitch Winehouse is a controversial figure, who some accuse of exploiting his daughter’s fame for his own enrichment. I’m not going to dissect how he fared in his moral and parenting responsibilities—that’s an entirely different kind of article. But I will say this: he’s a confident, skilled jazz singer. I doubt people would pay much attention to him, if his daughter wasn’t so famous, but he doesn’t embarrass himself behind the microphone.

It’s worth digging into Amy’s early life for insights on this aspect of her craft. And her father is a good source for this information.

“Despite her charm, ‘Be Quiet, Amy!’ was probably the most heard sentence in our house during her early years,” Winehouse writes in his book Amy, My Daughter. “She just didn’t know when to stop. Once she started singing that was it. And if she wasn’t the center of attention she’d find a way of becoming it.”

At age three she gave a spontaneous show of song and dance for her older brother’s birthday—who proceeded to pour his drink on her. She was always surrounded by music, and sang along to the jazz and big band music her father played at home or in the car. But she also delighted in hip-hop and R&B sounds from the US. At age ten, she even formed a short-lived rap duo with her best friend Juliette Ashby, calling themselves Sweet ‘n’ Sour—Amy was Sour. The two girls only rehearsed, never performed.

At age nine Amy began taking occasional classes at the Susi Earnshaw Theatre School, gaining her first formal training in singing and dancing. At age twelve, she won a scholarship to the Sylvia Young Theatre School in London, and her audition even got written up in The Stage. It’s all too fitting that her audition song was  “On the Sunny Side of the Street”—a jazz standard popular with African-American singers who crossed over to popular acclaim, but composed more than a half century  before Winehouse was born.

Her application to the school includes an essay where she spelled out her goals:

I want to go somewhere where I am stretched right to my limits and perhaps even beyond.

To sing in lessons without being told to shut up (provided they are singing lessons).

But mostly I have this dream to be very famous.

She wasn’t even a teenager yet, but she already knew what she wanted—and was aiming as high as she could dream. And her dreams were sky high.

I sometimes wonder if she would still be alive if she hadn’t been quite so famous. Maybe even a less lucrative career as a jazz singer would have been a better decision, at least for fans like me, and for Winehouse’s own survival.

Who knows? But I do wonder what she could have done if she had been able to record with the best jazz musicians in the world. And it might have happened. Her relationship with Tony Bennett would have opened doors for her. Not doors to fame and fortune—those were already at her beck and call. But imagine Winehouse collaborating with the Maria Schneider Orchestra (as David Bowie did shortly before his death), or working with Kamasi Washington (as Kendrick Lamar has done), or making music with Fred Hersch (as have Renée Fleming, Audra McDonald, and other crossover vocalists).

Call me crazy, but I can picture her sitting in with Paul Motian’s band or The Bad Plus at the Village Vanguard. I can envision her doing duets with Gregory Porter or Esperanza Spalding. In my mind, I can see her singing in the cacophonous midst of Sons of Kemet, or going into the studio with Flying Lotus, or hiring Jacob Collier to produce her next record.

Those things will never happen, but make no mistake. Amy could have handled every one of those situations, and not only would have risen to the occasion, but revealed new aspects of her musical persona she never got the chance to demonstrate before.

Fans gather at the statue of Amy Winehouse in Camden Town, London (Wikimedia Commons)

We live in an age when jazz has entered into a new dialogue with popular culture. We see it everywhere. Consider those Lady Gaga or Kendrick Lamar albums. I even hear that the leading K-Pop megastar band BTS wants to record with Kurt Elling and is turning its fans on to Chet Baker. Could you even imagine something like that a few years ago? And Hollywood movies have gone even further, turning to jazz as a touchstone for excellent in a dozen or so major films of recent years, from Soul to La La Land. This is where the loss of Amy Winehouse hurts the most. She could have been a key linchpin connecting the two worlds—of real jazz and glitzy pop culture.

I believe she was the natural leader of this exciting dialogue. She had the deepest jazz roots of any of those popular artists, and could enter into the jazz frame of mind while making no concessions or compromises. Perhaps that inability to make concessions shortened her life, who knows? But on stage, that absolutely unforced authenticity, vulnerability, and risk-taking would have taught us something about music we didn’t already know, even about something as venerable and explored as jazz.

And that’s why I make a case for her in the jazz pantheon. Half of my case rests on what she did, and the other half on what she had the capability of doing, but never got a chance. There are a lot of stars in the pop firmament, but when her star went out, there was no one large enough to take its place. Perhaps that sounds like hype but the music she left us—all too little, all to brief—is still there to remind us.