Amy Winehouse’s 20 greatest songs – ranked!

After all its emotional strife, the Back to Black album concludes with a jokey paean to weed. You could construct an argument that Addicted is Winehouse once more tapping into a venerable jazz tradition – it’s easy to imagine Fats Waller singing about someone snaffling his stash in the 30s – but perhaps it’s better to just enjoy its mordant wit.

If Winehouse’s posthumous Lioness collection frequently offered the sound of the bottom of the barrel being scraped – she simply didn’t record that much material – it occasionally came up with something great, as on this 2003 outtake that turns the old Ruby & the Romantics hit into charming soft-hued reggae.

For all the breeziness of the music – live-sounding drums and guitar, pretty woodwind – time has lent a grim irony to the lyrics of Help Yourself, which reflects more kindly on the same relationship that inspired Stronger Than Me. “I really empathise, looking through your bloodshot eyes,” she sings. “I can’t help you if you won’t help yourself.”

Winehouse auditioned for her record label, backed only by an acoustic guitar; you can see video footage of it 在里面 2015 documentary Amy. She’s in the same setting on the demo of Frank’s I Heard Love Is Blind, a striking example of how fully formed her vocal talent was barely out of her teens.

There were plenty of other 00s artists dealing in retro soul, 但, aside from her voice, one reason Winehouse stood out was her willingness to dig into the genre’s history. Certainly no one else was releasing songs like Wake Up Alone, audibly inspired by the music of soul’s 50s forefathers.

When Winehouse complained that the songs from Back to Black were too emotionally distressing for her to perform live, her father suggested she sing standards instead. As her Soul II Soul-esque take on Thelonious Monk’s most famous composition proves, she could have done that in considerable style.

The opening track on her debut album, Stronger Than Me won an Ivor Novello award. Were it released today, it would more likely cause a storm over the gender stereotyping in its lyrics, which might obscure what a great song it is: jazzy guitar chords over a stark, sampled backing, Winehouse in particularly strident form.

Winehouse clearly loved reggae, 但, on record, she had a tendency to let her enthusiasm get the better of her. For instance, she charges at Andy and Joey’s You’re Wondering Now, for once missing the darkness in the lyrics. Her own Just Friends is far better than her reggae covers, an understated, lilting groove, ungovernable lust in the lyrics.

On arrival, Amy Winehouse was lumped in with the post-Norah Jones wave of MOR female singers, which in hindsight seems extraordinary. There’s certainly nothing middle of the road about Fuck Me Pumps, an excoriating, viciously witty, take-no-prisoners attack on Wag culture set to a deceptively sweet melody.

Video footage shows Winehouse racked with nerves before meeting Tony Bennett to record her father’s favourite song, but you wouldn’t guess it from the finished results. On Winehouse’s last recording, months before her death, she sounds utterly in command and seemingly unbowed by the company she’s keeping, taking risks with her vocal.

One of Back to Black’s lighter moments, although there’s no mistaking the darkness and emotional torment that lurks behind its snappy one-liners – “you ain’t worth guest list” – Me and Mr Jones borrows its title from Billy Paul, its sound from early 60s soul and poses the eternal question: “What kind of fuckery is this?”

A highlight of Winehouse’s debut album, Frank, In My Bed’s sound is equal parts blaxploitation soundtrack and lush Philly soul – by way of hip-hop. For a study in contrasts, compare the lyrics with those of You Know I’m No Good: same topic – cheating – but a completely different tone, more defiant, less emotionally wrenching.

A posthumously released suggestion of what might have been, the only song Winehouse completed for her third album suggested an artist digging in musically and emotionally. The sound is unfashionably doo-wop inspired, the lyrics a troubling drawing of a volatile relationship: “I’d take a thousand thumps for my love.”

Her cover of the Zutons’ 2006 single is the most inescapable Amy Winehouse track of all, but if you want evidence of her skill as a stylist, here it is. Far more than Mark Ronson’s 60s soul arrangement, it’s her vocal that transforms the song, transforming the lovelorn original into something that crackles with lubricious intent.

Winehouse’s debut album didn’t really prepare the listener for what happened next, but you occasionally get a hint. What Is It About Men? is a brutally frank dissection of her father’s affair, her parents’ subsequent divorce and its lasting impact on her. Behind its soft soul facade, it’s deeply uneasy listening.

Back to Black usually works because the music perfectly complements the mood of the lyrics, but Tears Dry On Their Own works for precisely the opposite reason. The lyrics are alternately dejected and angry – the closest they come to positivity is resignation – but the song soars and the chorus feels exuberant.

A weird song to remain ubiquitous in the decade since its author’s death, effectively someone with addiction issues insisting they don’t have a problem for three and a half minutes. Rehab should be tough listening in light of what subsequently transpired, but it isn’t. The tune and the arrangement – and indeed Winehouse’s defiant vocal – are just too irresistible.

A grimy, guilt-ridden depiction of a dissolute relationship rocked by mutual cheating – “who truly stuck the knife in first?” – You Know I’m No Good’s lyrics are hip-hop inspired, filled with telling details and sudden plunges in emotional temperature: “I cried for you on the kitchen floor.” Winehouse’s voice and the sleazy-sounding horns heighten the mood.

The greatest example of the synergy that existed between Winehouse and Ronson. Her melody line sounds effortless, her lyrics switch between romantic agony and earthier concerns – “you like blow and I like puff” – while his production is the ideal companion: a brilliant homage to 60s girl group melodrama that feels original, never like pastiche.

It was one thing to cover, or make music inspired by, the Great American Songbook in the mid 00s – that kind of thing was everywhere – but another thing entirely to write an original song that could genuinely have passed as part of the Great American Songbook. Love Is a Losing Game is a song that arrived sounding like a standard, as if it had existed for decades, rather than being freshly written by a 23-year-old. Covered by Prince and named by George Michael as his all-time favourite song, it’s Back to Black’s desolate centrepiece, its least showy, most heartbreaking moment. Its live incarnation, stripped back to guitar and Winehouse’s vocal, is better yet.

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