Life lessons from Amy Winehouse and Taylor Swift

Amy Winehouse’s death in 2011 is the only celebrity death that has ever made me cry. As a rule, I get irritated by this sort of behaviour; sadness, shock and nostalgia are all understandable - I felt all of those when Prince died, for instance, and when George Michael died - but literal weeping over the death of someone you don’t know always seems a bit performative to me. Still, there it was: when I heard on the radio that Winehouse was dead I let out a loud involuntary ‘honk’ like a labrador gagging on a grass stalk, which is how I discovered that I was crying. 

It wasn’t that I was a superfan; I wasn’t. Lots of things annoyed me about her, from her dirty feet to her dirty hair. I didn’t much like her first album, Frank, and scat singing bores me senseless whoever’s doing it. I didn’t like the messiness that gave the tabloids so much material: the booze and the drugs, the volatility, the whole mascara-streaked-vulnerable-goth-pixie thing. I’ve known girls like that, and they’re a pain in the arse. 

But despite my unwillingness, Winehouse blew my mind in a very specific way. Beneath the knowing, damaged, little-girl-lost image was a merciless, acidic intelligence, and to my surprise she modelled a type of emotional courage for me. In the normal run of pop music, worldly wisdom flows from the 20-something artist to the teenager in the bedroom. But Winehouse was younger than I was, by a good decade, and our life stages - to put it mildly - were out of sync. I was in my mid-30s when Back to Black was released; I had a mortgage and two kids. I listened to it while making dinners, washing PE kits, and driving to the gym for my Bums and Tums class. She wasn’t supposed to be teaching me anything. But she did. 

In my own impressionable teenage years I’d come to believe a series of incredibly dumb things about romantic love. I believed that love had a precise scoring system, like tennis, in which somebody wins and somebody loses. I believed that the winner - who, as we know, takes it all - was the person who could demonstrate that they were the most beloved, ideally in front of their co-workers or other onlookers. And I believed that carefully cultivated indifference was the crucial mechanism by which a woman could get the man she wanted. Or rather, not necessarily the man she wanted, but the man who wanted her; I had somehow come to believe that being loved was more important than loving. 

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You’ll notice that this entire crapulous credo is a recipe for passivity. It would take a long time to explain where I’d got this nonsense from; I genuinely blame Jane Austen for quite a lot of it. (As The Guardian’s magnificent TV reviewer Nancy Banks-Smith once said, Pride and Prejudice is basically Cinderella.) ‘80s teen films didn’t help either. But in my defence, I don’t think I was particularly unusual. When this boneless manifesto was written up in The Rules, the dating handbook for women published in 1995, it sold millions. 

Don't Talk to a Man First
Don't Call Him and Rarely Return His Calls
Always End Phone Calls First
Always End the Date First
Don’t Open Up too Fast

The Rules, Ellen Fein (1995)

Unsurprisingly, I struggled terribly with this model for years. I’ve never been much of an actress, and my clumsy attempts to appear insouciant had predictably dreadful results. I was unusually slow to recognise that these dumb fucking rules specifically disbar you from action, leading to an emotional hall of mirrors in which the only thing that matters is what other people do, and what other people think about you. What you think about them is essentially irrelevant. Over time my own authentic responses became harder and harder to discern, disappearing like underused muscles, and I concluded that I was just unusually incompetent. (On reflection, I was definitely unusually incompetent.)

There’s one final rule in this credo, a rule of last resort. It’s exemplified by Gloria Gaynor’s ‘I Will Survive’, which is the song you have to dance to with your girlfriends when a relationship ends: 

And so you're back
From outer space
I just walked in to find you here with that sad look upon your face
I should have changed that stupid lock, I should have made you leave your key
If I'd known for just one second you'd be back to bother me
Go on now, go, walk out the door

What it boils down to is this: if a relationship ends before you are ready - that is, if you have incontrovertible evidence that you are not the most beloved - you can still pull out a last-minute victory (love is a scoring game, remember) by pretending you don’t care. Whatever agonised conversations you are having with your friends, you must never let a man know how much he has hurt you. Hurt was all I ever was, so for me at least this final rule had the merit of utility.

So this was the thing, years later, that astonished me about Winehouse. There was this drunken young strumpet, all mouth and mess, telling the whole wide world how much a man had hurt her. I was gripped by her remorseless public dissection of her own humiliation; I kept prodding at her lyrics, trying to work out what she was doing. She told us: he hurt me like this, like this and like this, and I still love him and want him back. She sang about the ugly, powerless bits - the anger and bitterness and snot, the victorious love rivals, the begging - and turned them into fuel for her immortality. She told everyone how much she cared, and she made magic from it. Was this… winning? 

His face in my dreams seizes my guts
He floods me with dread
Soaked in soul, he swims in my eyes by the bed
Pour myself over him, moon spilling in
And I wake up alone

Winehouse, ‘Wake Up Alone’

I think this is what I was crying about when I heard that she was dead. I really, really wanted her to win, to live a long life of success and money and adoration; I thought she deserved it. But I was also learning a lot from her, a lot of very enlightening things that hadn’t been in The Rules. I wanted her to live to be old, so that she could carry on explaining me to myself. 

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Over a decade later, I fell down a Taylor Swift rabbit hole in an impeccably middle-aged way: I read a ‘Best songs of the 2010s’ article in The Times and thought ‘Ooh, I’ve never heard any of these’. Within a couple of clicks I was listening to Swift’s 2021 re-recording of her song ‘All Too Well’, and experienced a familiar sensation. Here was another young woman - young enough to be my daughter, this time - whose emotional courage eclipsed my own.

Part of what fascinated me about Winehouse was her defiant legibility; after listening to Back to Black once or twice it’s entirely possible to write a couple of paragraphs about the love quadrangle she’s describing, and to feel that you know the dramatis personae. And of course, we did know at least two of them. Part of Winehouse’s tragedy was that she and her husband became unwilling tabloid stars; we could put faces and names to the people she was singing about, a real-life soap opera with the nation’s face pressed up against the window. 

Given her practice of dating celebrities, Swift is similarly unable to write a song without it being immediately associated with an identifiable man. But like Winehouse, instead of being stymied by this she practises radical self-disclosure. Millions - possibly billions - of people know that ‘All Too Well’, which is an incredibly specific diagram of pain, is about Jake Gyllenhaal.  But somehow, like Winehouse, Swift turns this - and the prospect of Gyllenhaal thinking ‘blimey, she was really into me huh?’ - into a win. This is partly because it’s a great song, and writing a great song must be an extremely satisfying way of wrapping up a bad relationship. But the even greater victory is Swift’s assertion of her own emotional validity. Nothing - not being dumped by Jake Gyllenhaal, not the legions of people watching, and certainly not any misplaced sense of shame - stops Swift from expressing herself.

I still think that while Swift is wonderful, Winehouse - pulverising and relentless - is greater. Swift repeatedly has it both ways (and who on Earth is going to stop her?), swinging between sentimentality and cynicism; she alternates between protesting against romantic tropes and being captivated by them. She regularly cedes the viewpoint to her lover, objectifying her own ‘red lips and rosy cheeks’, imagining herself seen ‘standing in a nice dress, staring at the sunset’. She can’t quite give up the idea of unforgettableness as revenge, or as power (‘Someday when you leave me/ I bet these memories/ Follow you around’). The spoken-word drawl on her post-breakup track ‘I Forgot That You Existed’ - ‘It isn’t love, it isn’t hate, it’s just indifference’ - is simply cringey.

But Winehouse disdained it all. She seemed amazingly untroubled by anything that anybody else thought, and gloriously unaware of the concept of romance. She eradicated every last speck of self-objectification. There were no anthems of faux-amnesia for girls to dance to; she invested nothing in pretending to forget or in straining to be unforgettable. She insisted instead on her right to yearn after a man who was unforgettable himself. The only viewpoint that interested her was her own. Perhaps her real-life unravelling made her incapable of dissimulation, but her ability to banish externalities, to sharpen her own experience to a diamond point, defined her greatness. 

Though I battle blind
Love is a fate resigned
Memories mar my mind
Love, it is a fate resigned

Winehouse, ‘Love Is A Losing Game’

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