1. ’Round Midnight
Although Amy Winehouse attended the Brit School and was initially on Simon Fuller’s management books alongside S Club 7 and Gareth Gates, her heart belonged to jazz and 1960s girl groups. In itself, her idolisation of Dinah Washington and the Ronettes distinguished her from almost all newly minted pop singers of the early 2000s; her exceptionally-susceptible-to-heartbreak voice did the rest. Yet she didn’t exist in a retro bubble. She covered the jazz standard ’Round Midnight as the B-side to her second single, Take the Box, and produced a freewheeling track that reflected her less publicised love of hip-hop and Latin. Even more than the version used for the B-side, an alternate take presents her as young and in love with music: she scats, vamps and plays with the beat, just because she can. The influence of Erykah Badu and Lauryn Hill is obvious, and there’s a touch of cabaret, but at around the 1:10 mark she casually bends a series of notes, and the rest of the track flows from there. As one of the most covered jazz songs, ’Round Midnight presented a challenge, but she was completely at ease with its yearning and sensuality.
2. What It Is
The B-side of Winehouse’s debut single, Stronger Than Me, this track complements the A-side’s contemptuous romantic side-eye. Stronger Than Me sneers: “You treat me like a lady and you my ladyboy.” What It Is stingingly concurs: “Your attitude became a bore … Mr Ultrasensitive, I’ll never let myself forget you.” It’s the kind of blanket condemnation that really demands an answer record from the maligned Mr Ultrasensitive. Taken together, the songs signal her disdain for beta males (who are further criticised for not being able to “separate sex [from] emotion” on In My Bed). The A-side was bracing enough to win the 2004 Ivor Novello award for best contemporary song, but it’s the flipside that really warrants attention. Accompanied only by acoustic guitar, Winehouse is completely unadorned, and at the peak of her vocal powers. Her fluidity makes it sound simple, yet she’s fully engaged with the lyric – the disappointment in her voice can’t be feigned. This recording makes it easy to understand why her future record company spent several months tracking her down after hearing her singing backing vocals on another artist’s demo.
3. Fuck Me Pumps
Winehouse came of age just as the Wag phenomenon got off the ground, and Fuck Me Pumps is her riposte to women whose life’s work was “getting with” footballers and other rich targets. If there was one thing she hated, it was a “skank” and her “Gucci-bag crew”, so her easy-swinging delivery on this song is deceptive, because it conceals real venom: “Don’t be too upset if they call you a skank / Cos like the news, every day you get pressed,” she croons, adding for good measure: “Don’t be mad at me cos you’re pushing 30 / And your old tricks no longer work.” The spite was so authentic that you have to wonder whether Winehouse had had a run-in with some brassy gold-digger – or maybe she was just a north London hood girl who called it like she saw it. (She held her childhood idols Salt-N-Pepa in high esteem because “they were real women who … talked about girls they didn’t like”). Either way, Fuck Me Pumps was one of the highlights of Winehouse’s first album, Frank. It was almost unheard of for a mainstream female singer to use the F-word as a song title – on the song itself, she sings “F-me pumps” rather than banning herself from radio play by saying “fuck” – and the track excited a good deal of attention. The attitude it bespoke – forthright and uncompromising – turned out to be the real deal.
4. We’re Still Friends
Winehouse frequently covered other artists, which could yield spirited-but-WTF moments like her bash at Toots and the Maytals’ Monkey Man. But when she remained within her soul/R&B comfort zone, she could be a fantastic and fearless interpreter. Her languid retread of the Shirelles’ Will You Love Me Tomorrow proves her ability to put her own stamp on things, but straightforward covers, such as this version of Donny Hathaway’s We’re Still Friends, are equally impressive. Recorded at London’s Union Chapel in late 2006, it’s so faithful to the original that it copies the opening piano riff (she used it again, note for note, on Back to Black’s title track). Yet the tenor is very different. The lyric is a conversation between a former couple who run into each other on the street, and agree that the friendship they’ve managed to salvage is better than nothing; where Hathaway barely keeps back the tears, Winehouse approaches it with a bruised dignity. Until the 1.30 mark – then the dam cracks and it’s obvious how much the dignity is costing her.
5. Back to Black
Back to Black, Winehouse’s 12m-selling second studio album, signalled a complete change. He new co-producer, Mark Ronson (with Salaam Remi), orchestrated a shift towards R&B that edged her into a more commercial lane, but the fresh direction was underwritten by a series of what can only be described as terrible life choices. A drug-drenched relationship with Blake Fielder-Civil publicly recast her as a brawling bad girl; she romanticised the hopelessness by refusing to go to rehab. (For all its status as her biggest hit, Rehab is nowhere near her best song.) Back to Black’s title track was inspired by a split with Fielder-Civil, who temporarily returned to a previous girlfriend: this spare acoustic version is crushing.
6. Me and Mr Jones
“What kind of fuckery is this?/ You made me miss the Slick Rick gig!” she tuts on this Back to Black track – almost certainly the only time the British-American rapper has been mentioned in a song influenced by doo wop and Phil Spector. Winehouse’s sense of humour didn’t often surface, but the turbulence of her life hadn’t quite quashed it: Me and Mr Jones contains some of her best one-liners, and there’s a witty duality in itself in this marriage of rap-loving Londoner and 1950s American soul. “It’s about how a fella I used to see didn’t get me in to see Slick Rick, which upset me, but when he … got me in to see Nas, I thought, ‘You know, I don’t even like you that much,’” she explained. When she performed the song at London’s Bloomsbury Ballroom in September 2006, before Back to Black’s release, there was already talk about her personal life, but she rose to the occasion, giving Me and Mr Jones the full woozy-coquette treatment. If her wattage had been tangibly dimmed by her lifestyle, there was no hint at that point that it was more than a passing problem; if anything, according to some of the showbiz journalists at that gig, her only real task would be getting her career back on track in the face of competition from young hopeful Lily Allen, who had made inroads on what was considered Winehouse’s audience.
7. You Know I’m No Good
The Arctic Monkeys covered this on Radio 1’s Live Lounge in 2007, absolutely nailing its self-loathing, but Winehouse’s original has the edge in terms of pure, killing desolation. While recording Back to Black, her relationship with Fielder-Civil lurched from crisis to drug-fuelled crisis and she was feeling it: “She never wanted drugs, she just wanted love. She was into somebody, she would go all or nothing,” remembered producer Salaam Remi, who worked on her unfinished third album. This is the album version of You Know I’m No Good, which doesn’t include the Ghostface Killah verses that were tacked on when it was released as a single. Anyone who hasn’t heard the track without Killah’s trumpetings (“Once you go Ghost, you never go back,” he advises, rather missing the tenor of things) needs to listen to the original; it’s one of the great expressions of romantic despair.
8. Rehab (Jay Z remix)
Winehouse’s love of hip-hop dated back to when she was 10, and, inspired by Salt-N-Pepa, formed a duo called Sweet’n’Sour (unsurprisingly, she was Sour). With a sympathetic rapper aboard (see also: Like Smoke, featuring Nas), Winehouse’s material acquired a jolt of modernism. Rehab’s familiar jauntiness is counterweighted by Jay Z’s funny but foreboding verses: “Amy should have rehabbed him, ’stead she doubled his ration / Can you blame me for being a slave to my passion? / My heroine flows more lethal than Marilyn’s nose/ I’m an OD ’til I’m in peace like Anna Nicole / Hov! ” Getting into the spirit, he sings part of the chorus with her – a duet nobody ever thought they’d hear.
9. Wake Up Alone
Winehouse and Fielder-Civil got married in May 2007, and divorced two years later, with Winehouse declaring their “whole marriage was based on doing drugs”. This Back to Black track feels like a portent that the union would be short-lived, depicting an almost ghostly confusion and despair: “He gets fierce in my dreams, seizes my guts / He floors me with dread / Soaked in soul / He swims in my eyes by the bed”. Musically, it’s a country/doo-wop homage that incorporates the rawboned sincerity of the former and the sass of the latter – an improbable stylistic cocktail that Winehouse pulls off by going hard on the country pathos and leaving the doo wop to the backing vocalists. Surprisingly, when she played the song at live in September 2006, she delivered it as a testament of her devotion to Fielder-Civil, who was in the audience. Spotting him, she mouthed “I love you”; given the deep depression expressed in the song (“I stay up, clean the house, at least I’m not drinking / Run around just so I don’t have to think about thinking”), her co-dependency is awful to behold.
10. Body and Soul (with Tony Bennett)
Reportedly her last recording, this Grammy-winning March 2011 duet brought Winehouse together with one of her idols. The 11-minute video of the studio session reveals her nerves as she arrives at Abbey Road Studios: “I’ve got my lyrics, I know the song,” she stammers, to the bemusement of the unflappable Bennett. “I’ve never done anything like this, to sing with one of my idols.” Her jittery chat – she’s palpably shocked at being told there would be no rehearsal before recording started – was excised from the official video, obviously, leaving only the song, which has the two singers finding remarkable empathy. The longform version is more interesting: four months before she died, Winehouse was vulnerable and trying to hold it together, but her voice doesn’t let her down.
