Five songs that prove Amy Winehouse was a timeless talent

When Amy Winehouse tragically passed away in the summer of 2011, the shock it wreaked on the world was unmatched, as it really felt as though the final spark of true originality in music was gone forever.

The only small sliver of consolation in this bomb of heartbreak was that, for all the devastation of her young life cut far too short, Winehouse died a bona fide legend. Some can strive to match that same adoration across an entire lifetime and never achieve it, but all she needed was two albums in her 27 years to soar beyond the stars. After all, it was her voice that did all the talking.

As such, her untimely death in itself cemented Winehouse with an untouchable seismic legacy – joining the likes of Jimi Hendrix, Janis Joplin, and Jim Morrison in the so-called ‘27 Club’, it proved definitively that the singer seemed transplanted from another time and orbit. Her 21st-century surroundings were never quite worthy of her power, and her transcendence as an artist was an unparalleled asset which left the whole world, whether old or new, in complete and utter awe.

From classic crooners to modern pop stars and everyone in between, Winehouse’s ability to capture the world and transport it to an alternate reality was like nothing seen in music before or since. However, with only two albums released within her lifetime, it’s also difficult to cobble together her greatest hits without simply reeling off her complete discography. Yet away from the bright lights of her biggest songs, that’s where you’ll find a selection of some of Winehouse’s most timeless gems.

Five of the most timeless songs by Amy Winehouse:

‘Love is a Losing Game’ – Back to Black

Amy Winehouse - Singer - Musician - 2007

‘Love is a Losing Game’ is easily classed as one of the singer’s crown jewels, but it still harbours much less of a mainstream vibrance than the likes of ‘Valerie’ or ‘Tears Dry on Their Own’. Indeed, it was the lowest-charting effort out of the entire length of Back to Black, but its oozing enamour of blue-eyed soul retrospectively gives way to what should be lauded as one of the greatest songs ever written.

It was a testament to the song’s beguiling heart and power that it most famously captured two of the world’s often most acerbic hearts, in the form of both George Michael and Prince. The former lauded Winehouse as he hand-selected ‘Love is a Losing Game’ as one of his essential Desert Island Discs picks, while the regal monarch of rock himself loved it so much that he started performing it at his gigs, even inviting Winehouse to accompany him in London. In that sense, the track was certainly anything but a loss.

‘Me and Mr Jones’ – Back to Black

Amy Winehouse

Responsible for one of the best – and, in turn, endlessly relevant – opening lines in the history of song, ‘Me and Mr Jones’, “What kind of fuckery is this?”, instantly cemented Winehouse as someone with a definitively original view of the world. It was also fittingly one that she didn’t give two fucks about making clear, which was a major part of the reason that she became such a beacon to the younger masses, as well as timeless to the old. 

Evidently calling back to the likes of Billy Paul with his gender-swapped original, Winehouse’s irreverent ability to turn things around and call out the status quo was not only what made a song like ‘Me and Mr Jones’ so original, but also meant it could have been situated alongside the classics. The lyrics, of course, reflect a searingly contemporary London in the mid-2000s, but it’s almost as though time and place melt away under the thumb of a master. 

‘Stronger Than Me’ – Frank

Camden- Amy Winehouse's spiritual home - 2023

As a whole, Winehouse’s debut album Frank is wildly under-appreciated when it comes into comparison with its follow-up, Back to Black, but ‘Stronger Than Me’ undeniably emerged as its standout as the singer began the process of turning heads. But following much of a similar suit to the likes of ‘Love is a Losing Game’ meant that the transcendent song only received its flowers at a much later appeal. 

Becoming the lowest-charting song of the album, and subsequently also of Winehouse’s entire career, the legacy of ‘Stronger Than Me’ is largely at odds with its initial lacklustre reception. But within this, you also witness a change of the times, because there is enough of an argument to suggest that the world simply wasn’t ready for a song of that nature at the time. Rather than conforming to patriarchal norms, the tune threw the notion of petting man’s ego straight out the window, and thus Winehouse should be considered in her own separate league along with it. 

‘Take the Box’ – Frank

Ranging right from the bottom of the tree of Frank to the top, ‘Take the Box’ may have been the most successful single of that album, but its legacy has somewhat been squandered in favour of its more chart-friendly counterparts. It goes without saying that the song similarly embodies a timeless spirit – but in this sense, now that time has worn on a decent chunk, it’s easy to forget that it is now actually 22 years old. 

Through this lens, looking at the music video for ‘Take the Box’ now, it’s almost disarming to see Winehouse at how young an age she was. Fame and its demons had not yet curled their grip around her – she is fresh-faced, without the hair, the makeup, and much of the exuberant persona. On one hand, it was a tragic prism of what was to come, but also the special realisation of the moment in which a star was born.

‘Body and Soul (ft. Tony Bennett) – Lioness: Hidden Treasures

Tony Bennett - Amy Winehouse - Split

Then, winding right to the end, you get to Winehouse’s final ever recording – her duet with Toby Bennett on ‘Body and Soul’, which was released on the album Duets II by the latter in March 2011.

Subsequently being re-released six months later, after the young singer’s passing and to mark what would have been her 28th birthday, it remains the ultimate swan song for a seismic but all too short life and career. 

Recalling the poignantly-tinged memories, Bennett revealed afterwards that Winehouse said she was nervous at the prospect of recording with one of her absolute idols. But on the flipside, the feeling was clearly mutual as the classic crooner fittingly commented after her passing: “If she had lived, she would’ve been right up there with Billie Holiday and Dinah Washington. It’s just a tragedy.”

As much as this is true, Winehouse’s life was defined by so much more than just its ending. That’s the mark of what makes her timeless – knowing that her music lives on forever.

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