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Revisiting the 15 Greatest Amy Winehouse Performances on YouTube

Singer Amy Winehouse
Photo: Ross Gilmore/Redferns

There’s a brief turning point in Amy, the stirring new Amy Winehouse documentary that came out this weekend, where we momentarily forget the embattled singer’s fate. She’s been off drugs for months, living in St. Lucia and starting to look and sound like her pre-fame self. We hear her leave cheerful voice mails to producer Salaam Remi, letting him know how elated she is to be healthy enough to get back in the studio after an extended hiatus. Amazingly, you almost start to believe she’ll be fine. The illusion fades fast as soon as those closest to her — namely her father, Mitch, and manager, Raye Cosbert — talk her into doing a small comeback tour in Europe to convince all her naysayers that we haven’t seen the last of her.

Amy wasn’t ready. One of her best friends makes a desperate attempt to hide her passport so she can’t leave the country. Instead, her family and management check her into rehab — this time she couldn’t say, “No, no, no” — to wean her off booze long enough to survive a tour. That’s when it becomes clear that Amy has lost the will to fight: She’s completely dead-eyed, now doubting her own progress. And so she relapses — hard. During the final performance seen in the film, at 2011’s Belgrade Festival in Serbia, she gives up on herself. In painful footage, we see her barely lucid, refusing to sing, and unable to go on with the show despite her band’s reassurance. Like everyone else in Amy’s life, they can’t help her, and she’s ultimately booed off the stage. The European tour is later canceled, and Amy dies of alcohol poisoning a month later, at 27.

While there’s no way to discuss Winehouse’s legacy without touching on her tragic end, we’d all be better served to spend our time remembering how incredible of a performer she was at the peak of her powers. To that end, we parsed through YouTube and dug up some of her greatest live performances. Her window was brief, but at its best it was beautiful.

15. “Cherry,” Glastonbury, 2007
Amy had a voice forceful enough for an outdoor festival and a stage presence fit for a jazz lounge. She married the two strengths during a statement set at Glastonbury in 2007 by reaching into her back pocket with a bluesy cut from her 2003 debut album Frank. You can skip ahead to 10:05 to catch her woo the crowd with “Cherry,” but I recommend watching the full concert.

14. “We’re Still Friends,” unknown
If the video quality weren’t so poor, this performance — one of the two Donny Hathaway covers on the list — would rank much higher. His influence pierces through her sound, and she interprets his work like a student who’s become the master. (In the lyrics for “Rehab,” she sings, “There’s nothing you can teach me / That I can’t learn from Mr. Hathaway.”) Thankfully, one fan captured her version of his blues staple “We’re Still Friends” for the rest of us to play on loop from now until forever.

13. “Take the Box/In My Bed,” Wembley Arena, 2004
Fans of post–Back to Black Amy might be surprised to learn she’d already been booking gigs at respected venues like Wembley Arena well before her beehive updo appeared. She used to play guitar live, too. Here’s a fresher-faced, confident Amy doing just that with back-to-back performances of songs from her underappreciated first album Frank.

12. “You Know I’m No Good,” Shepherd’s Bush Empire, 2007
Truthfully, Amy was never at her best when performing the hits that catapulted her career to global success. (Recycling a song for publicity purposes will age it quickly.) But there’s something about playing at a favorite hometown venue, as Amy calls Shepherd’s Bush, that can reinvigorate an oldie-but-goodie. The fact that she also filmed this show for a concert film, 2007’s I Told You I Was Trouble: Live in London, probably didn’t hurt. More from that later.

11. “I Heard Love Is Blind,” SWR3 New Pop Festival, 2004
As unforgettable a vocalist as Amy was, she never saw quite the same level of praise for her songwriting — despite writing or co-writing every one of her original songs. This gem from Frank has her offering the least convincing apology for cheating since Shaggy’s “It Wasn’t Me.” But because she turns on her charm so well, it’s hard to find a reason not to play along. This isn’t Amy the singer, it’s Amy the actress.

10. “Valerie,” unknown
How do you improve one of your most well-known covers? Switch it up with what looks like an unrehearsed acoustic rendition that could’ve come about simply because Amy was bored and someone put a microphone in front of her. That’s how good she was.

9. “Rehab,” The Late Show With David Letterman, 2007
When Amy made her U.S. television debut on Letterman, America probably didn’t know what it was in for. A doo-wop-sounding Brit with Aretha Franklin–size chops singing about addiction? Amy never looked more pleased with herself than in this very moment. The twinkle in her eye screams, You ain’t seen nothing yet, wankers.

8. “Teach Me Tonight,” Jools Holland’s Annual Hootenanny, 2004
If anyone was qualified to channel Dinah Washington, it was Winehouse. She was more than an old soul; most of the time she sounded like a time-traveler. Case in point: Her cover of Washington’s “Teach Me Tonight.” If you didn’t know better, you’d think you were listening to one of your grandmother’s favorite old records. In the Amy documentary, Questlove remembers how astounded he was to discover that Amy was a jazz scholar even more knowledgeable than himself, a longtime student of the genre. This is that knowledge on display.

7. “He Can Only Hold Her/Doo Wop (That Thing),” Shepherd’s Bush Empire, 2007
Winehouse and Lauryn Hill never collaborated, sadly, but our ears likely couldn’t have handled it if they did. Luckily, Amy realized they were a pairing fans would enjoy — and then simulated it with an unforgettable mash-up that utilizes Sharon Jones’s incomparable band, the Dap-Kings, to sublime effect. (Don’t forget: They, too, played a crucial role in Winehouse’s success.)

6. “Stronger Than Me,” Later … With Jools Holland, 2003
In a perfect world, “Stronger Than Me,” Amy’s debut single, would’ve been a hit. It never caught on, but Amy’s dominating performance of the song on British TV makes it worth revisiting. With loose hair, fewer tattoos, and a guitar strapped across her body, this Amy might seem unrecognizable given the drastic changes her image underwent during the subsequent years. But it’s the one we should all miss the most.

5. “Tears Dry on Their Own,” Later … With Jools Holland, 2006
Amy almost always saved her best TV performances for her home country, and rightfully so. Americans fell hard for Amy long after she brought down the house on Jools Holland for the umpteenth time. But over in the U.K., she was already a household name. Moments like this are why.

4. “Wake Up Alone,” Shepherd’s Bush Empire, 2007
To know Amy, one can assume, was to know her humor. Over the years, as she receded into the darkness of drug addiction, her playful wit rarely peeked through. But she let it slip while flubbing an introduction to this song. Watching her search for ex-husband Blake Fielder-Civil in the crowd so she could mouth the words I love you said it all — regardless of how dangerously toxic we now know that relationship was for both of them. That dark humor of hers will sink in the second it hits you that the song she just dedicated to the love of her life actually mourns his loss.

3. “I Love You More Than You’ll Ever Know,” Le Live de la Semaine, 2007
The world probably loved Amy more than she ever knew. But there’s no doubting that Donny Hathaway would’ve loved her enough for all of us after hearing this divine homage. If Winehouse didn’t get you excited about the future of the blues, allow her to remind you of what could’ve been.

2. “Back to Black,” Silver Bullet TV, unknown
Winehouse’s early years consistently proved that she never needed much more than a guitar and a microphone to make a statement. Even when you think she’s just standing there totally disinterested in the performance at hand, she couldn’t be more invested in the words leaving her mouth. Her greatest power was making it look so effortless.

1. “Love Is a Losing Game,” Mercury Prize, 2007
When most people think about the night Winehouse truly became a star, one singular image gets triggered: The 2008 Grammys, when a bewildered Winehouse took home five awards and gave us one of the most memorable Grammy reactions of all time. It’s also one of her most unguarded moments. But there’s an even more important night in Amy’s career that predicted her near-sweep at the Grammys. In 2007, Winehouse made the short list for the Mercury Prize, the award for the best album in the U.K. She went head-to-head with the Arctic Monkeys, Bat for Lashes, and more — but ultimately lost to the Klaxons. (Her second loss in four years.) Unfazed, she took the stage to perform “Love Is a Losing Game” for what might just be the best vocal performance of her career — or certainly ever broadcast — with her most trusted stage setup: just her and a guitar. Those Grammys the following year were an added bonus — as this performance proves, Winehouse didn’t need to win anything to get everyone talking about her.

Ranking the 15 Best Amy Winehouse YouTube Videos