The true story behind two iconic performances in the new Amy Winehouse biopic 'Back to Black'

Critics and fans alike threw around terms like "once in a generation," and with good reason. Nobody, not even the music legends she idolized, sounded quite like her. That signature growl rivaled the tone of Louis' trumpet, marrying blues, jazz, soul, and rock into a modern medley that was entirely her own.

Her potential seemed limitless, but an extreme (and highly publicized) battle with substance abuse and alcoholism ultimately cut her life short. Winehouse died on July 23, 2008, at 27, leaving an indelible legacy in her wake.

Peter Macdiarmid/Getty; Dean Rogers/Focus Features

The new biopic Back to Black tries (and, in our critic's opinion, fails) to reexamine that legacy through a dramatized lens, tracing the arc of Winehouse's upbringing, influences, successes, and struggles. Directed by Sam Taylor-Johnson (Fifty Shades of Grey, Nowhere Boy), the film notably revisits iconic moments from Winehouse's career, including her stellar performance at the 50th Grammy Awards in February 2008. 

Industry star Marisa Abela dons the beehive updo to play the artist, shouldering the unenviable task of singing Winehouse's standards for the film. 

The film recreates two famous Winehouse sets: the aforementioned Grammys performance in 2008 and, just a few months later, her appearance at the Glastonbury Festival, which was equally memorable but for all the wrong reasons. Below, we revisit those two watershed moments and explore their significance in Winehouse's legacy nearly 20 years later.

Winehouse sings "You Know I'm No Good"/"Rehab" via satellite at the 50th Grammy Awards

Back to Black was the singer's sophomore album, preceded by the soulful but less transcendent 2003 LP Frank. Though her debut sold over a million copies in the U.K., 2006's Back to Black was both more guttural and refined, the work of a generational talent coming into her own. The record also made her an international sensation, selling over 16 million copies and earning her a whopping six nominations at the 50th Grammy Awards. 

Due to visa complications, she couldn't attend the ceremony in person. Though U.S. officials reversed their initial denial, the singer — who had recently entered a rehabilitation clinic for substance abuse — couldn't prepare for a performance in Los Angeles. Instead, she temporarily left the facility for the awards show, tuning in to the festivities via satellite from a studio in her native London. 

Peter Macdiarmid/Getty

It was the setting her style of music is meant for, the low light and velvet trappings of an intimate jazz club rather than the commercial expanse of the Staples Center. During the live broadcast, she sang a stunning rendition of "You Know I'm No Good" that seamlessly melded into lead single "Rehab." Winehouse was entirely in her element, swaying to the sultry songs like a furl of smoke and improvising inflections on the lyrics with aplomb. She alternated between crooning staccato and gleeful shrieks as she waved to her loved ones.

The performance was abuzz with kinetic energy, thanks in no small part to her stellar accompaniment, complete with brazen brass horns and live-wire backup singers. Taylor-Johnson brought that same band into the fold for Back to Black (they were present offscreen while filming the iconic Grammys performance). 

"It was priceless but also so emotional to have those guys on set," Taylor-Johnson said in a statement.

Amy Winehouse wins Record of the Year for "Rehab" (among other accolades)

Winehouse took home five trophies that night, joining Lauryn Hill, Alicia Keys, and a handful of others in the ranks of female artists who have won that many victories in a single evening. She notably beat a pre-Fearless era Taylor Swift for Best New Artist and snagged Song of the Year for "Rehab." But her win for Record of the Year was the moment that went down in music history. 

Her fellow nominees were formidable: Justin Timberlake, Rihanna, Foo Fighters, and Beyoncé. R&B artist Natalie Cole (daughter of Nat King) presented the category along with legendary jazz singer Tony Bennett, one of Winehouse's idols and influences. (Her last studio recording was with Bennett at Abbey Road Studios just four months before her death). 

Winehouse watched them rattle off the nominees with wide eyes from her makeshift stage half a world away, gripping the mic stand and, ever one to speak her mind, taking a swipe at fellow contender Timberlake. ("His album's called What Goes Around Comes Around?!"). Her name was last in the lineup, prompting whistles and cheers from the London crowd and a wry smile from the singer. But the room didn't erupt until Bennett announced her as the winner. 

Amy's reaction has gone down as one of the most iconic moments in the award show's history. Her grin settled into a disbelieving, pinch-me-so-I-know-it's-real gape. She stood still and stunned as her band jumped for joy before enveloping her in a loving embrace. Her dad, Mitch, joined the huddle and kissed his daughter on the cheek. She then staggered, arms outstretched, to her mother, Janis, whispering something in her ear while the audience chanted her name. 

She celebrated the moment alongside friends and family but not her husband, Blake Fielder-Civil, who introduced her to hard drugs and was arrested in November 2007 following an attack on a bar owner. "For my Blake, my Blake incarcerated," Winehouse said in her acceptance speech. She also shouted out Mark Ronson, her frequent collaborator and creative partner who produced "Rehab" — who is notably absent from the film Back to Black. 

No matter how many times you rewatch the clip, you'd be hard-pressed not to feel an emotional pang. It's the moment an up-and-comer was forever cemented as one of the all-time greats, displaying humility, authenticity, and ecstasy in equal measure.  

It should have been one of the best nights of Winehouse's life, and maybe it was. She was successful, surrounded by loved ones, and, at the time, sober. However, in the 2015 Oscar-winning documentary Amy, her longtime friend Juliette Ashbya said a dark cloud still hung heavily over the singer. 

"I was so overwhelmed. I was so proud of her. And I was just flashing our whole life, our childhood, and then [Amy] saw me crying. She grabbed me, pulled me up on stage, and took me off the stage. And I was having a bit of a panic attack," Ashby recalls in the doc. "I said, 'I can't believe this is happening. This is amazing. I'm so proud of you.' And I'm looking at her, trying to get some form of reaction, and she went, 'Jules, this is so boring without drugs.'"  

Watch Amy Winehouse win Record of the Year for "Rehab" at the 50th Grammy Awards below.

Amy Winehouse performs (and bombs) at the 2008 Glastonbury Festival

Winehouse's notoriety predictably skyrocketed following her Grammy's sweep, but she had long been tabloid fodder due to her highly publicized bouts of heavy drinking, drug use, erratic behavior, and health issues. Still, the surge in popularity and unrelenting harassment by paparazzi exacerbated her instability and struggle with sobriety, which was apparent during many of her live performances. Such was the case with her infamous set at the 2008 Glastonbury Festival in England, depicted in the biopic Back to Black. 

Along with Jay-Z, James Blunt, and Martha Wainwright, Winehouse was one of the headliners on Saturday, June 28. Tens of thousands of fans gathered for her performance at the Pyramid Stage, which started relatively well with renditions of "Addicted" and "Just Friends." The mood of her set worsened, however, when she brought up her still-incarcerated partner before singing "Back to Black." 

"My husband is out of jail in two weeks," she said to scattered jeers among the cheers, much to her disdain. "Who booed? I'll find you, take your phone, ring your mum, and tell her about your bad manners."

Jim Dyson/Getty

Things spiraled from there as she stumbled and mumbled her way through the rest of her set, making increasingly bizarre comments about having "never loved a white man" before Fielder-Civil and calling Kanye West a "c--t." By the time she closed with "Rehab," Winehouse was slurring the lyrics down at the barricade while audience members in the front row feverishly grabbed at her. She fought back later that evening by throwing punches at fans. Security promptly led her away to another horde of onlookers, and no charges ever came about, but the altercation capped the lackluster concert on an especially bitter note.

It wasn't the first time she had fumbled a set, nor was it the first time she sang at Glastonbury. After making a minor splash at the festival in 2004, her 2007 performance garnered acclaim and was even immortalized with a live album in 2022 for its 15th anniversary. But expectations weren't as high ahead of her 2008 homecoming. Per EW's coverage at the time, her reputation preceded her with a morbid rumor that Winehouse would be a no-show because she had died earlier that day. It was an inhumane sentiment that encapsulated the gross (and, sadly, prophetic) public consensus surrounding her at the time.

Why these performances matter

There's a stunning contrast between her electric showing at the Grammy's in February 2008 and her dilapidated turn at the Glastonbury Festival just four months later. Perhaps that's why Back to Black highlights these specific performances in her stacked but ultimately short tenure as a sensational singer. They paint a portrait of an artist who was simultaneously decorated and dismissed, adored and derided — and would be gone too soon.