One of the greatest, most iconic voices to emerge this side of the Millennium, London singer-songwriter Amy Winehouse was truly a one-off talent; fiercely witty, brutally honest, and astonishingly talented. During her rapid rise to fame, she faced intense tabloid scrutiny and was forced to attempt to deal with various addiction issues, all while in the public eye, and was treated cruelly.
The singer tragically died when she was just 27 years old, a young, incredibly gifted musician with so much more to give.
As a result of her short but hugely influential career, Winehouse left a lasting legacy on modern pop, which owes a great deal to her retooling of vintage influences, and her love of soul and jazz. And she left her mark elsewhere on popular culture too, not least as the subject of a major Design Museum exhibition and two documentary films, Asif Kapadia’s Amy, from 2015, and Marina Parker’s 2021 film Reclaiming Amy. In April this year a third film will be released, this time a feature: Back to Black, starring Marisa Abela (Industry) as the singer.
But what are her best tracks? We’ve had a go at whittling it down to the stone-cold classics.
10. Will You Still Love Me Tomorrow?
Will You Still Love Me Tomorrow? is one of those songs which usually has a great big ‘DO NOT COVER’ sticker whacked over the top of it; originally recorded by The Shirelles, Carole King (who, in fairness, wrote the song in the first place) is the only person to really do it justice. Aside from Amy Winehouse, who recorded a version for the soundtrack of a Bridget Jones sequel, of all things. A word of wisdom: skip the overproduced, schmaltzy version on her posthumous record Lioness, and head for the superior unplugged demo. Raw, unfiltered genius.
9. You Sent Me Flying/Cherry
The more downbeat companion song to Frank’s Stronger Than Me, this piano-led track is also slightly more underrated; perhaps because it boasts fewer sizzling one-liners. Still, don’t overlook it: powered by tight keyboards and lazily scuffing snares, the song unpicks Winehouse’s embarrassment as she tries to woo and impress an older man with her taste for Erykah Badu and Marlboro Reds. Its brief, bossa-nova add-on Cherry is just another bonus.
8. F**k Me Pumps
A highlight from Winehouse’s debut album Frank, F**k Me Pumps relentlessly takes the piss out of aspiring WAGs over a sharp, hip-hop inspired beat, and while the lyrics aren’t exactly what you might call ‘feminist’, they’re undeniably very amusing. “Don’t be too upset if they call you a sket, ‘cause like the news, every day, you get pressed,” she quips. Ouch. And then, just when she’s settled into a comfortable roast routine, the final verse takes a surprisingly sentimental turn. “Without girls like you, there’d be no fun, we’d go to the club and not see anyone.”
7. Valerie
There are very few cover versions out there which completely eclipse the original, but Amy Winehouse’s take on Valerie occupies a place on the relatively short list. First released as a chugging indie anthem by Liverpool band The Zutons in 2006, the two acts first crossed paths during an argument at Camden boozer The Hawley Arms. According to Zutons’ singer Dave McCabe, a random punter started praising Winehouse and slating his band; after he lost his patience told said stranger to “f**k off”, Winehouse told McCabe to do the same. After he stormed off, she gave chase. “She goes: ‘Come back! I really like ‘Valerie’,” McCabe said. “I’m not really arsed about you, but you must be alright ‘cause you wrote that song.’
“Even when I think of the song now, I think of how she sings it – that’s just what it has become. I don’t think anyone else in the world could have done that,” he added.
6. Rehab
For obvious reasons, the deceptively-chipper sounding Rehab takes on a dark new tone following Winehouse’s death. “I ain’t got the time, and if my daddy thinks I’m fine,” she protests, “they tried to make me go to Rehab, but I won’t go, go, go.” It’s also emblematic of the singer’s sheer honesty, and her willingness to dig right into the darkest corners of her life.
5. Wake Up Alone
A lot of Winehouse’s finest lyrics are incredibly direct, but Wake Up Alone is a more abstract and poetic take on heartbreak, at least by her standards. Though the verses get straight to the point, her narrator frantically cleaning the house to try and stay away from the sauce, the choruses of this swooning soul song are menacing dreamscapes. “He’s fierce 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.” Damn.
4. Back to Black
While much of Winehouse’s best stuff owed a great deal to the jazz greats, her second album’s title track feels like one big tribute to doo-wop, Sixties girl groups such as The Supremes and The Ronettes, and the soul labels Stax and Motown. But it’s when those spiralling strings kick in – with levels of epic showiness fit for a Bond theme – that this one really pops off, Winehouse making typically brutal sense of her fraught relationship with Blake Fielder-Civil. “He left no time to regret, kept his dick wet, with his same old safe bet,” she snarls.
3. You Know I’m No Good
Gutsy and packed with welly, Mark Ronson’s bright, brassy production on Back To Black as a whole had an influence on pop that is difficult to overstate; so many artists after Amy have tried their hand at her hyper-crisp expression of neo-soul, but very few have pulled it off with as much charm. Though it’s hard to pick a favourite Winehouse song that features Ronson behind the mixing desk, You Know I’m No Good surely comes out on top, that creeping bassline and those biting snares elevating her observational lyrics. Every word of this is gold, but a special mention goes to the verse that effortlessly rhymes “bitter” with “chips and pita”.
2. I Heard Love is Blind
According to collaborator Felix Howard, Winehouse rocked up at the first ever recording sessions for Frank in a pair of worn-out jeans with Sinatra’s name embroidered across the back pockets; and as you’d expect, the influence of jazz standards, and timeless retro-tooled sounds are all over her debut album. While she undoubtedly harnessed these influences well, the thing that truly made Winehouse a special talent was her unique lyrical voice. Even when she was laying bare insecurity and self-loathing, sadness dripping from her voice, the words themselves were razor sharp and dripping with wit. On her most bittersweet song, her narrator performs all manner of logical gymnastics, in full view of the listener, to try and justify cheating. “Why’re you so upset? Baby, you weren’t there and I was thinking of you when I came,” she sings, each word landing like a dagger to the gut.
1. Love is a Losing Game
When George Michael appeared on Desert Island Discs in 2007, he picked Love is a Losing Game as his favourite track of all time. “This is the best female vocalist I’ve heard in my entire career, and one of the best writers,” he said. Winehouse and Michael later performed the Back in Black track together as a duet; she also sang it live with none other than Prince. It’s easy to see why both musical icons were so infatuated with it; though it was released in 2006, it has the timeless air of a beaten-up classic from a decade past. While many of Winehouse’s best songs give a knowing smirk, even when they’re wallowing in self-loathing, this one is a big, emotional pit of hopeless regret.
