The poignancy of Love is a Losing Game – the Ivor Novello-winning fifth single from Amy Winehouse’s final album Back to Black – only seems to deepen with the passing years. To mark twenty years since Back to Black was released, we’re taking a closer look at this pivotal track, examining how Amy channeled her own heartbreak into one of her greatest ever songs.
Before we look at the song, however, we need to understand the context in which it was written. Amy’s second album Back to Black was made during a period of intense personal tumult for Winehouse. Her tempestuous relationship with boyfriend Blake Fielder-Civil had come to an abrupt end – leaving Amy despondent.
It was a factor, amongst other things, that pushed her deeper into an unhealthy fixation with alcohol and drugs. The pair had split a mere six months after beginning their relationship, with her mercurial partner returning to the arms of his ex. In the fall-out, Amy’s feelings of utter dejection spurred her to write the lion’s share of Back to Black.
Meanwhile, Amy’s label Island Records were growing impatient. Her debut, Frank, had been released to rapturous acclaim in 2003, however Winehouse was retrospectively disappointed with the record’s ‘smooth’ and polished sound – and what she perceived as a bungled marketing campaign.
“You couldn’t rein her in, you couldn’t tame her and there was no point in trying to. She wouldn’t comply, rightly or wrongly, and with the benefit of hindsight that’s someone that knows her sense of self,” remembered Island Records’ A&R legend Darcus Beese in an interview with Music Week. “She was one of those artists where you just had to get out of her way.”
Her next album then, would be something altogether more self-directed, and more in sync with Amy’s increasingly varied musical touch-points. Back to Black’s 11 songs would present a more honest reflection of Amy Winehouse in the mid-2000s, both as a blossoming artist and as a battle-worn, fallible human being.
Initial recording sessions with Frank producer Salaam Remi bottled some true magic. Most notably, Remi and Winehouse crafted the sublime Tears Dry on Their Own (which we’ve explored in depth in a separate feature), Some Unholy War, Me & Mr Jones, Just Friends, and Addicted. But it was the portion of the record that Amy made with her new friend, upstart producer Mark Ronson, that would lead to Amy’s strongest-ever clutch of songs.
Meeting Ronson – with whom she shared a publishing company – the pair quickly hit it off on a creative level.
“Even though I wasn’t a big producer at that time I was just happy to have any gig,” Ronson told NME. “I remember people being like, ‘Oh, you’re working with Amy Winehouse, good luck with that. I heard she’s been working on that album forever’.
“The six songs that we did on Back to Black together, we did in five to seven days,” Ronson continued. “I always think, ‘Damn, I wish it did take longer’, because I would have more memories. Not that we didn’t spend plenty of time hanging out after that, but it was just so quick.”
Working with Ronson at his New York studio, Amy and Mark developed six new songs. Firstly, the gloomy, piano-based title track alongside lead singles Rehab and You Know I’m No Good. Then came Wake Up Alone (co-written with Paul O’Duffy) and He Can Only Hold Her (co-written with Richard and Robert Poindexter).
But, perhaps the song that would go on to have the most abiding resonance would be the shimmering Love is a Losing Game.
Written while Amy was processing the emotional shock of being abruptly discarded by the man with whom she had planned a future, Winehouse poured her feelings of fragility, and a sense of detached resilience, into a lament for love more broadly.
Lyrically, she pointed to the idea of love as being akin to a game, with two players taking a gamble on something impossible to know the outcome of.
In Amy’s hard-learned case, it was a risk that hadn’t paid off…
For you, I was a flame
Love is a losing game
Five story fire as you came
Love is a losing game
One I wished I never played
Oh, what a mess we made
And now, the final frame
Love is a losing game
To compound the analogy, Amy’s allusion to a ‘final frame’ recalled her penchant for a pool table, amid references to poker chips and a losing hand of cards. It was a strong and fitting conceit that revealed much about Winehouse’s own philosophy.
Beyond the personal specifics, Love is a Losing Game also spotlighted Amy’s wisdom. In her words, there’s a sense of cosmic inevitability to the fractured promise of love. Her experience seemed to prove a universal truth, that love is always a game we’re all destined to lose, one day…
Though, though, oh, I battle blind
Love is a fate resigned
And the memories, the memories mar my mind
Love is a fate resigned
Over futile odds
And laughed at by the gods
Despite the contemporary media portrayal of Winehouse as an off-the-rails hell-raiser, Love is a Losing Game’s lyrics demonstrate, perhaps more clearly than anything else, that she was a mature songwriter beyond compare for her age.
Ridden with contemplative emotion, in conjunction with the wistful, jazz-informed chord structure that Amy had crafted the song within, it was firm evidence that Amy’s abilities were flourishing.
“Amy’s musicality… she was like a monster, and I definitely want everybody to know that,” Mark remembered when addressing the crowd during an Amy Winehouse tribute performance alongside Yebba at London’s The Roundhouse, ahead of performing Love is a Losing Game.
“The chords were so complicated and jazzy, I was like, ‘Man, you just play this song. I don’t even know what I’m doing right now.’ So she did.”
Feeling that the song’s simplicity needed to be retained, Ronson recorded Amy performing the song with just an acoustic guitar.
It was perfect.
“I’d become so attached to it that I felt there was no way we could top that emotionally. But there was a part of me that still wanted to hear the sonic of reverbed drums in the background,” Mark remembered in an interview with Performing Songwriter.
Ronson turned to a couple of members of Amy’s then-backing band, the Dap-Kings to figure out if it was possible to develop the arrangement without tarnishing the song’s beauty.
“I sat with [Dap-Kings band members] Gabe [Roth – bassist/bandleader] and Homer [Steinweiss – drummer] and asked them, ‘How can we put a beat behind a ballad like that and not remove any of the sentiment?’ That was a real challenge: coming up with a beat that wouldn’t detract from the song and still become an integral part of it. With a song like Rehab or You Know I’m No Good it’s a lot easier because you can put something hard behind it that’s going to drive the track. Coming from DJ’ing, you’re always thinking about the beat but sometimes I have to shut down that side of my brain and remind myself it’s not about that.”
Realising that the jazzier heart of the song needed to be brought to the fore, Ronson, Winehouse and Roth devised a more instrumentally-coloured arrangement. A steady drum performance was laid down by Steinweiss, with a distinctive fill that opened the song and recurred before each verse. Crystalline electric guitar chops were applied by Binky Griptite and Thomas Brenneck, and understated bass from Nick Movshon.
Wanting to emphasise the emotion even further, Ronson and conductor Chris Elliot penned an orchestral backing. Originally, this was a little more overwrought than the subtler final result.
But Ronson wasn’t sure how Amy would take the idea, having previously heard her being dismissive of the concept of cheesy-sounding strings. Particularly considering the personal stakes behind this stark and deeply emotive piece.
Mark tried his luck…
“I said, ‘I’ll pay for it then. If you don’t like it, we can take it off’,” Ronson remembered in an interview with Red Bull Music Academy. “She was like, ‘Don’t waste your f**king money.’ She really just wouldn’t have it, so I had to do it without telling her. I did the strings without telling her. I went and did the arrangement.”
Having spent a day mixing the new arrangement, Mark was nervous about playing back the results to Amy.
“She didn’t know I’d put the strings down until we’re mixing the final thing. At that point we’d been mixing the song for the whole day. If she’d just come in and said, ‘Take the strings out,’ it would’ve been a pain in the ass and kind of ruined the record. So she’s listening with her head down in the console for two and a half minutes. And I couldn’t see the expression on her face and I’m like, ‘Oh, please, let her like it.’ And she just jumps up at the end of the song and goes, ‘Come here Ronny-chops,’ and gives me a hug”.
Although Amy wasn’t without notes…
“Without missing a beat she says, ‘Just take that Mariah Carey harp bullshit out at the third breakdown, alright?’ and walks out of the room. So that was that,” Mark recalled.
Amy’s long-awaited second album was worth the wait, becoming nothing short of a phenomenon. Topping charts globally, it would, of course, go on to scoop five Grammys and sell over 20 million copies.
Love is a Losing Game would go on to become one of Back to Black’s immediate highlights. For many, it was the record’s emotional centre – the crux of the album’s thematic exploration of heartbreak.
“I had never really made a hit record before,” Ronson reflected in an interview with the BBC. “It didn’t sound like anything else that was on the radio. It certainly didn’t seem like something that was going to be this huge commercial success. It just felt raw and honest.”
Sadly, Winehouse’s unexpected death at the young age of 27 on July 23 2011 tragically ended her journey. Love is a Losing Game, in fact, stands as her final ever single release – chosen as the fifth song to be put out from Back to Black on December 10 2007, well over a year since the best-selling album was released. Thusly, it entered the charts at a lowly 46 – as most people were already very familiar with it.
Even Amy herself apparently saw little point in releasing the single. Personally, things had changed a lot. Now reunited and married to Blake, she infamously never turned up for the song’s planned video shoot.
Lifelong best friend Tyler James shared in his book My Amy: The Life We Shared, that on that day, the onus had been on him to ensure the increasingly unpredictable Amy attended the shoot.
“A huge, elaborate set was hired at Pinewood Studios, a street had been built, there were plans for fake rain,” said James. “As usual, it was all on me to try to get Amy there. Amy had stayed with Blake the night before; I got there in the morning, there were a hundred people waiting for her, and [director] Phil Griffin was frantic. ‘Please, please, Tyler, you’re the only person who can get her here.’”
After calling Winehouse and telling her how brilliant the design for the video looked, Tyler could hear Winehouse asking Blake whether she should go along. Blake said no. Options for how to proceed were limited…
“Me and Phil had to make the video for Love Is a Losing Game,” James recalled. “We had editing equipment installed in a spare hotel room and put the montage of images and performances together. We wanted Amy to be involved. She did come in once. She said, ‘I don’t care, you and Phil do it, you know what I like,’ walked out the door, swung the door back open, and said, ‘Make sure you put in loads of Blake!” And that’s why he’s in it.’”
Interestingly, musical titan Prince soon recognised Love is a Losing Game’s beauty, and took to performing the song in his live set during his 21-night residency at London’s O2 arena in September 2007.
“I love the song,” Prince said during a press conference, and answered in the affirmative when asked if he’d be up for a live duet with Amy herself.
Once she learned of the prospective offer, Amy was flabbergasted. “I’m going to Minneapolis – see you later,” she joked when MTV informed her of Prince being up for a duet. “I hope I can do it, though – I’ll drop everything to do that,” she said.
Although they never shared the stage during Prince’s main stint at the O2, Winehouse did join the Purple One during one of his legendary after-parties on September 22 2007 at the neighbouring IndigO2 venue.
Prince and Winehouse performed the song together on stage (only this grainy footage remains, sadly) with the former in true form – elaborating on the song with a slew of slinky guitar lines and a vibrant solo. “I got tears – I’m gonna have to get my shades on,” Prince said after they’d finished their rendition.
Love is a Losing Game cuts to the very heart of Amy Winehouse, and remains a testament to her talent. Rightfully, it won the Ivor Novello Award for Best Song Musically And Lyrically in 2008. In the wake of her death, the song’s emotions only hit harder.
“I was with her two nights before she died and I spoke to her on the phone two hours before she went to sleep for the last time,” remembered bassist and live musical director Dale Davis in a new interview with The Times. “I wasn’t worried. Completely the opposite. We had such a nice conversation. She rang up, she said, ‘I’ve been watching YouTube clips of myself, I can sing, can’t I?’ I went, ‘Yeah, of course you can sing, you’re the best.’”
