In the cramped backseat of a taxicab on the way to the summer Connecticut wedding of a barely remembered coworker, the conversation turns to death. Maybe the impending nuptials have the cast of Comedy Central’s Broad City in a serious mood this morning (dog nuptials later prove to have a similar effect). “You know,” confesses Lincoln (Hannibal Buress), “I’m still not over Amy Winehouse. It’s like, we knew it would happen, but we didn’t do anything about it. I didn’t know her know her, but I still miss her.” There are several operative levels to the joke here. It’s funny that Lincoln’s been thinking about Amy Winehouse constantly since she passed away in 2011, because it’s never been indicated before. It’s funny that he seems to harbor some residual guilt over Winehouse’s death, because he’s such a good guy that he has nothing else to be sorry for. It’s funny because it’s relatively removed from the sphere in which the rest of the conversation takes place. It’s funny because Lincoln reveals a sentimental attachment to Amy Winehouse, of all people, and thus stirs up a whole bunch of odd associative images. The line is also funny for another reason: because it’s so true. And even in this sense, there are multiple possibilities for the joke. Lincoln’s confession is true, because we really did “know it would happen” yet “didn’t do anything about it” — and it’s also true because this is precisely the sort of retroactive, crocodilian gushing expected from those who knew and yet did nothing. Funny, in that way where you have to laugh to keep from crying.

“We knew it would happen, but we didn’t do anything about it” is just the sound of a few years tacked onto “I’m not really that surprised, to be honest.” That’s the refrain I heard again and again in 2011 when Amy Winehouse was discovered dead from alcohol poisoning. As Pitchfork’s Jess Harvell put it in an obituary for Winehouse: “[P]ublic reaction to the news says quite a bit about the arc of her short career, most of it very sad and some of it downright ugly. While distraught, not even her fans seem…particularly surprised that Winehouse died.” Like Lincoln, I still miss Amy Winehouse, and it never ceases to horrify me that her story ends this way, rank with the stench of an appallingly jaded and uniquely twenty-first century cynicism. No one was “surprised” three years prior, either, when a video made the internet gossip-blog rounds depicting Winehouse smoking crack. Winehouse’s lifestyle was rough when things were ostensibly going well, and rough in another way altogether when she was low, and the world’s nosiest cameras caught it all in a way that’s ubiquitous now but was still more than a little alarming even in the post-shaved-head-Britney aughts. The result was that her sudden passing was not regarded as sudden at all; it was seen as merely another troubled tabloid event in a predictable tabloid life, a foregone conclusion sprung from an inherently flawed premise. Sifting through the record now, it’s hard to parse whether a given obituary is being serious when it mentions that, for example, Winehouse had fallen off the wagon three days prior to her death, or whether it’s deploying that particular detail for melodramatic effect. The genuine public mourning for the singer — a tree outside her London home was converted into a candlelit shrine by grieving fans — was all tangled up with too many R.I.P.s soured by an undertone of unperturbed derision. “I told you so” is not really an appropriate response to anyone’s death — is it ever a productive response to anything? — but it was prevalent in responses to the news about Winehouse, even though it was occasionally delivered through very real tears.

Winehouse spent her whole career being ruthlessly scrutinized and judged. This is par for celebrities nowadays, especially female celebrities, and especially those female celebrities who are so readily perceived as occupying the second position of the cultural Madonna/Whore dynamic. Something that really isn’t surprising is that a person like Winehouse didn’t react passively to fame. Her on-stage/on-camera persona was all about giving zero fucks, as it’d probably be put in 2015’s internet parlance. She often didn’t have any control at all over the way she was being represented in the press, but when she did, she used it as an opportunity to play up her rebellious streak. Mostly, this meant using a lot of curse words in situations when no curse words at all would’ve worked just fine, but it did the trick. Ultimately, public exposure turned into a lose-lose for Winehouse, because she couldn’t tell the press to fuck off without giving them exactly what they wanted: footage of her telling them to fuck off. It was hard to tell when she was reveling in the spotlight and when she was reacting negatively to the privacy violations that come with star status, because in her case those things looked and sounded very similar to one another. A deplorable 2007 Rolling Stone cover story on Winehouse bore the title “The Diva And Her Demons,” as if the diva and here demons were legibly distinct. She was a diva because of her demons, or she was a diva in spite of her demons, or the demons were the personification of her diva-ness? The alliteration makes it sound like the demons are the diva’s backing band, like they’re on her side, or maybe on her shoulder, whispering bad advice in her ear. Were they?

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Putting the audience in the position of not quite being sure what’s real and what’s fake wasn’t just the way Winehouse interacted with the paparazzi; it was her whole M.O. A white Jewish girl from north London singing blue-eyed soul in front of the Dap-Kings? Subjecting authenticity to doubt was Winehouse’s principal strategy as a celebrity and as an artist (if those aspects can even be separated). She nearly demanded interpretation, on stage and off. Every time you encountered her, you had to decide whether she was acting out as part of a debauched performance or out of real distress; whether she was really singing soul or just engaging in a subtle kind of blackface. (It’s hard to imagine her making it through the thinkpiece grinder in 2015 with her reputation intact.) She was brutally honest about herself and yet she refused to be straight with us. I don’t know if it was happenstance or strategy that so many elements of the story boil down to these kinds of blurred lines, and that, in itself, is of course just another blurred line. Strategy or no, this backfired spectacularly. Naturally, confronted with a figure so confusing, commentators gravitated toward clear and rigid positions, and those positions were often unfriendly to her, cutting Winehouse off from sympathy. Tabloids weren’t the only publications that treated her like dirt: in 2007, Salon ran a piece by James Hannaham that declared Winehouse to be 100% racist schtick. I don’t find it coincidental that so wholesale a rejection of Winehouse’s art and lifestyle opens with the sentence, “We’re all expecting Amy Winehouse to die,” a line that was unacceptable then and is shameful now. The plural first-person is a rhetorical strategy designed to eclipse protest. It’s indicative of how Winehouse was received at large, alive or dead. If you weren’t expecting her to die before you read Hannaham’s essay, he certainly sowed the seeds of anticipation. Here, refusing to take Winehouse’s engagement with soul music at all seriously synchronizes with a refusal to take her reaction to fame seriously, or her relationship to controlled substances, or, ultimately, her life.


When Winehouse died, she was instantly inducted into the “27 Club” of music industry stars who also met their ends at that early and supposedly cursed age. Only the most willfully ignorant proponent of the 27 Club’s mythology could fail to see a discrepancy in the way Winehouse’s death was received versus that of someone like Kurt Cobain, another rock star with a record of substance abuse (whom Hannaham offers as a counterexample to Winehouse’s alleged fakery). Cobain’s death was and remains the tragic full-stop to a romantic narrative that spins him as a soul too sensitive for this world, who turned to drugs as a form of relief from the same pain that he poured into his songs, who rejected fame. I think there’s a good deal of standard-issue sexism at work in the differences between the Winehouse and Cobain narratives. There’s also the simple fact that Cobain hid from the public eye as best he could. This is easier for men to do than women, and it was much easier to do in the pre-internet age. Consequently, for a long time there was relatively little public material about Cobain — far less, at least, than there was about Winehouse in 2011. In a sense, Cobain’s retreat from the limelight left a Cobain-sized void that the culture filled with stories, stories that grew into a mythology despite their occasional lack of verifiable roots. Winehouse wasn’t afforded the courtesy of an explanatory apparatus; it was all right there, an endless glut of information, much of it unflattering or incriminating.

But it’s all the wrong kind of information. What materials we do have on Cobain add to the story we’re already telling. At least we know he committed suicide, because we have the note to prove it. We know Winehouse drank herself to death, but we don’t know why. We don’t know if it was on purpose or not. (The Daily Mail reported that the last thing she did before she lost consciousness for the last time was watch YouTube videos of herself, a claim that says much more about the monstrous insensitivity of that publication than it does about Winehouse’s final moments.) One narrative or another could be constructed from the facts we have, but there’s no reason to believe any version in particular. For whatever reason — her personality, her way of reacting to the pressures of celebrity, the unequal treatment of men and women in pop culture, the nature of information consumption in the 2000s — Winehouse hasn’t merited a glamorous mythology to explain her sordid death. There was so much information circulating about Amy Winehouse that there didn’t appear to be much need to delve deeper. Thus, what looked sordid has stayed sordid. We didn’t need to know what happened to her, because we already thought we knew. “We [were] all expecting Amy Winehouse to die.” “We all knew it would happen, but we didn’t do anything about it.” We just wanted the exact number of her corpse’s blood-alcohol content, the cherry atop a really sad Sunday cover story.

Winehouse was an absolutely incredible musician who became known, instead, as an absolute trainwreck of a person — regardless of whether or not she really was an absolute trainwreck of a person, and certainly regardless of the degree to which this notoriety itself contributed to the trainwreck. We’re saddened, or awed, or sometimes even surprised when great artists die young. But women rarely get credited for being great artists. As a critical metric, the Grammys have long been deeply irrelevant, but if they ever had a flash of prescience, it was in 2007, when Winehouse won five awards in a single night for one of this millennium’s finest records, 2006’s Back To Black. Yet from her breakthrough until her death and even afterward, positive critical evaluation of her work has been drowned out by negative popular evaluation of her personality and behavior. This year, Winehouse is back in the pop-cultural imagination after a posthumous lull thanks to the new biographical documentary Amy. I haven’t seen the film yet. Hopefully it presents a balanced picture of its subject and resists melodrama (although the libel controversy that her family’s kicked up in advance of its release suggests otherwise). If nothing else, perhaps the uptick in public interest will allow for a clearing of the air and a refocusing of collective attention on the only aspect of Amy Winehouse we can truthfully say we know anything about: her music.

Hers was a perfectly ordinary speaking voice. But when she started to sing, damn if she didn’t have — and on record, doesn’t still have — one of the most arresting voices heard in the last two decades of pop music. Plenty of her 2000s peers have distinctive singing voices (I’ve never mistaken Ke$ha for anyone else), but no other pop singer could sing like Winehouse, not even Adele, her fellow British purveyor of blue-eyed soul. Winehouse’s forgettable debut album Frank is far from a showcase of her vocal firepower, but it does underscore the amazing raw material she had to work with. The production on her first big hit, “Fuck Me Pumps”, is so plastic, timid, and lifeless that it rips like gift wrap when Winehouse’s lithe voice, still growing into its potential, cuts through it. She sounds at once raw and poised, a fresh voice that sounds instantly vintage. A few years later, on the regal and heartbreaking title track from Back To Black, her voice has matured into this great big booming thing. On the somber bridge, she drops to the bottom of her impressive alto range to repeat the word “black” over and over with an emotive force so tremendous, it feels like the band has stopped playing not on cue but because they were momentarily too shaken to continue. Winehouse’s singing possesses, among other attributes, that kind of power, the power to breathe life into lyrical clichés and imbue rote sentiments with so much vivacity and gravitas that it sometimes comes off like she’s inventing rather than rehashing some of pop’s hoariest tropes.

A good deal of Winehouse’s gift has to do with her timing and cultural consumption. She sang 1960s girl-group and 1970s soul like the true 2000s pop omnivore she was. She keeps her balance against the rocking stresses of beats and basslines that belies her familiarity with dub reggae. On stage she swaggered confrontationally but ironically, a way of engaging with her band and her audience that probably derives from British rock’n’roll from the Stones on down to the Libertines. Above all other non-R&B genres, she owes an especially large debt to hip-hop and rap. She imbues every note with a chatty, street-smart toughness and gleeful profanity learned from the late-‘90s golden age of popular hip-hop. This is crucial to the effect of Winehouse’s music in two ways. First, it makes her seem not “edgy,” but merely contemporary, so that the older pop forms that make up the body of her work don’t instantly seem dated. Second, it updates the well-worn poses she strikes — often those of women abandoned or wounded, hopelessly in love, sunk in despair, blazing with righteous anger — for contemporary ears. “You love blow and I love puff” is as good a reason as any to end a pop-song relationship, I suppose, but I find it unlikely that ay singer would have uttered it before at least 1995 if not later. In 2006, Winehouse could use foul language to express rage or lust, for example, the way we do in everyday life, where her forebears had to rely on oblique inference and nonverbal expression. The rising popularity of rap made pop music at large more verbose and its language more quotidian. Winehouse’s music demonstrates awareness of this shift. She simultaneously proves that the forms of soul music can withstand the passage of time and that they require some updating in order to do so. Winehouse’s sonic aesthetic, like her fashion choices (that beehive!), initially appeared decades old but turned out, instead, to be utterly postmodern. When Ghostface Killah appeared on a remix of her single “You Know I’m No Good”, it sounded not anachronistic but logical. Winehouse found a way to write and sing soul in a way that sounds current and innovative while maintaining a deep respect for the traditions she drew from (with the vital assistance of smart producers and talented backing musicians).

Winehouse saw a fair share of criticism for appropriating black musical traditions, some of it less callous than the Salon piece. However, looking back from a post-Miley Cyrus vantage point, it seems we didn’t know how good we had it. Winehouse wasn’t just singing soul; she knew what the fuck she was doing. Her diction, syntax, and cadence are the result of careful, devoted listening — again, to rap, dub, and ‘90s pop as much as to Phil Spector comps, the Shangri-Las, and four decades of soul and R&B — rather than a few in-studio rehearsals. She wrote all her material, so when she complains during “Me & Mr. Jones”, “What kind of fuckery is this? You made me miss the Slick Rick gig!”, you can be sure that’s not some hired songwriter trying to lend Winehouse some black street cred. Disdain positively pours out of the side of Winehouse mouth when she snarls that line; this guy made her miss a Slick Rick gig, and she’s pissed about it because, evidently, she loves Slick Rick. I believe it, just as I trust that she really did think of Sammy Davis, Jr. as her “best black Jew.” This is one of the many things that made Winehouse stand out from the pack even when imitators began to appear. Someone like the long-forgotten Duffy, for example, sounds on her sole hit “Mercy” like she’s been trained in how to sing soul. The crackling vinyl vintage of her intonation is a little put-on, a little mannered. When Winehouse sang soul, it sounded like her own voice, erupting from dark and turbulent depths. If it wasn’t original, it was still fresh, it was still funky, it was still distinctive. And it was uncompromising — just like her persona.

Although a dud on American shores, Frank made Winehouse famous in the U.K., famous enough to afford big-name producers (Mark Ronson and Salaam Remi) and the Dap-Kings on backup. Holy hell, do those decisions ever pay off. Few pop records since Back To Black have sounded so confident, so playful, so raw, and so sophisticated all at once. Ronson and Remi slick the studio takes up with modern technology just enough, so that they still capture that live-band feel while making it camera-ready for 2000s pop radio and MTV. Live instruments integrate with airlifted elements of the mix. On “Rehab”, the strings appear to have been recorded in a different space entirely than the backing band, but they weave tactfully in and out of the mix, enriching the sound and mood without drawing attention to the cut-and-paste composition. Earlier in the song, there’s a chilling moment when Winehouse shifts into the voice of a counselor who tries to take sexual advantage of her. Notice how the first four words of that line — “Kiss me, yeah baby” — are mic’d up over the horns to draw attention to the dark intonation and the carefully deployed mixture of sexual aggression and debonair flippancy Winehouse uses to denote this other voice. The music is bold, gutsy, and dramatic. It plays into and extends the persona Winehouse projects while also ceding the center spotlight entirely to her.

So, like Winehouse herself, the music on Back To Black can also be very funny, as found in the little brass curlicues that punctuate the dubby rhythms of “You Know I’m No Good”. Indeed, it’s wit that seems, to me, to really open up the record as a whole. As the jaw-dropping sass of “Rehab” immediately makes clear, it’s a highly self-conscious collection of songs. If it’s not quite tongue-in-cheek, it definitely lays the irony on thick. It’s this irony, which reflects the way Winehouse interacted with the media and the public, that makes her songwriting so contemporary and so exciting. There are many funny musical moments on Back To Black — my favorite is the way the backup singers harmonize the words “dick to me” on “Me & Mr. Jones” — but for each one of these, there are a dozen in Winehouse’s lyrics and delivery. She was never just sad, or lonely, or hysterical, she was always aware of how contrived her postures of resignation and abjection could read, of how cliché it was for an inebriated woman to chew out her man for coming home late. “Back To Black” is almost too deliberately dramatic to function, straining under the hyperbolic burden of all the funereal piano chords, the florid orchestration, and that nearly a cappella bridge — but that’s part of why it’s so sad. Winehouse makes sure to underline every moment when she could turn herself into a joke, and then steps back from the brink of self-parody to land on something else instead. In the process she renders her performance all the more convincing. The stories she’s best at telling are heartbreaking: tales of failed relationships, cruel lovers, self-destructive tendencies, chemical dependency, mourning, hopeless nostalgia, terrible depression. Winehouse never sugarcoats her subject matter, but she also never wallows. She’s not self-pitying, but she is honest. She’s always trying to communicate the intensity of the emotion at hand while looking for any way out of it. Back To Black is a dark album, but by the time “He Can Only Hold Her” fades out with triumphant horns and backing vocals, Winehouse has learned how to live with her pain without denying it. Winehouse was a grown-up when she wrote these songs, and they’re about being grown-up.

So yeah, that means she sings about getting high, and fucking, and fucking while high. But it also means she sings about what motivates her to do those things, and how they aren’t always as satisfying as she’d hoped. She sings about surviving despite great adversity, and knowing herself well, loving herself in spite of her flaws. What’s more, she does this in the context of songs that are fun as hell to listen to. She knows deep hurt, but it doesn’t stop her from cracking a joke, or from dropping a shrill “woohoo!” at the outset of “He Can Only Hold Her”. She she knows that humor and joy don’t have to cancel out pathos. Amy Winehouse might have been regarded as a terrible role model — as a drunkard, a crazy bitch, a trashy whore, a crack-smoking disaster. Yet the way she picks up the pieces of her life and strides majestically into the sunset during “Tears Dry On Their Own” taught teenage me as much as any other musician about how to endure real emotional strife with requisite dignity, grace, and self-respect. Winehouse was wise, and I still learn from her songs every time I listen to them. That song’s clincher — “I fucked myself in the head with a stupid man” — is as emblematic of Winehouse’s lyrical brilliance as any. It’s so many things at once: self-recriminating and self-affirming, crass and truthful, bruised and humorous.

Winehouse’s slyest sleight-of-hand is, of course, “Rehab”. This song is a world-conquering blockbuster so thoroughly saturated with self-deprecation, meta commentary, facetious wit, coy allusion, and blatant irony that it might well have also been bluntly autobiographical, but we’ll never be able to sort those parts out from the cunningly elusive whole. Winehouse knew exactly how and why she magnetized public attention, and instead of dodging that attention, she spins around and looks her audience dead in the eye. On the track, she dares us to have any kind of reaction at all, to take the song literally or to declare it all a joke. It’s an undecidable song, I think, one that so frequently and emphatically undercuts its intimacies with ironies and its ironies with intimacies that straightening out all the kinks in the story becomes impossible. In any case, it’s a great song no matter how it’s taken. It’s equally smart and engaging whether it’s read as a confession, as a piss-off prank, or an entirely fictitious narrative, and Winehouse is equally convincing as ironist or short story writer as she is autobiographer. Should we take “Rehab” seriously? Did Winehouse take it, or us, seriously? We’ll never know. She sang with tempestuous force but she never disclosed that key piece of information in a way we could understand.

All of this confusion boxes the listener into a corner, so that eventually the initial questions become irrelevant because they’re unanswerable. They exist outside of “Rehab”. Listening to the song becomes a process of crossing into it, of letting the fuss about sincerity become secondary to the experience of the song itself. Interpretative difficulties remain, but because they can’t be settled, they also fade when placed next to the material they’re meant to explain. I’d propose that by making it impossible to comfortably situate “Rehab” in relation to Winehouse herself, Winehouse attempts (and at least partially succeeds) to force us to take the song on its own, internal terms. And it works on those terms, again and again. It was a stroke of genius, one whose influence is visible, for instance, in Taylor Swift’s recent, winking smash “Blank Space”, which aims for the same moving target as “Rehab” and only partially hits. With “Rehab”, Winehouse convinced the world to hear one of her songs for what it was and not what we read it as.

She also made it as clear as could be that she knew exactly what we might think of her, and that she had ways to turn this judgment to her own artistic advantage. She could pen a track that ticked every box on the “confessional pop song” checklist and still didn’t confess a thing, one that copped to every rumor spread about her while keeping her hand close to her chest. All the nasty stories, the viral video shares, the photos in Spin of her carving her fiancé’s name into her abdomen with a shard of broken glass…the self-congratulating narrative our culture tells about Winehouse is a poisonous one. We pretend to possess some sort authoritative knowledge of the woman herself, but this is knowledge that, I think it’s pretty clear, the culture itself generated. “I didn’t know her know her,” admits Broad City’s Lincoln, “but I still miss her.” Again, he speaks for us all. We know what Winehouse’s blood toxicity was at the moment her heart stopped beating, but we have only to listen to “Rehab” — the song that made her a star and which demonstrates all of her gifts as a writer and performer — to be humbled, and reminded that we didn’t know Amy Winehouse. Not half as well, anyway, as she knew herself.