Amy Winehouse’s Iconic Glastonbury 2007 Performance

The performance at one of live music’s biggest events captures the singer at the height of her powers.

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Amy Winehouse Live at Glastonbury 2007 cover
Cover: Courtesy of Universal Music

The first half of 2007 was a remarkable time for Amy Winehouse. The year began with her second LP Back To Black comfortably ensconced at the summit of the UK albums chart and in February, the Camden-born singer/songwriter bagged the BRIT award for Best Female Solo Artist. A month later saw Winehouse’s smash single “Rehab,” a frank self-portrait addressing her battle with addiction, conquer America by breaking into the US Top 10 while its parent album Back To Black rose to No. 2 in The Billboard 200, cementing the singer’s international fame. But arguably her crowning achievement came on June 22nd via a triumphant appearance at the world-famous Glastonbury Festival.

Winehouse had performed at Glastonbury before, in June 2004, where she was sandwiched between reggae singer Mikey Dread and blues-rock doyenne Bonnie Raitt in the Jazz World tent and mostly performed songs from her just-released debut album, Frank. Three years later, Winehouse’s career was dancing to a different groove; the languorous jazz stylings that defined her debut album had given way to a more robust retro-soul sound on Back To Black, which instantly chimed with the public and helped transform her into a global star. And she had a new image to go with it; Frank’s long-haired natural look had given way to a towering beehive hairdo and thick eye-liner, which one critic memorably described as “Ronnie Spector meets the bride of Frankenstein.”

Listen to Amy Winehouse’s Live At Glastonbury 2007.

Back To Black‘s success heralded a dramatic rise in Winehouse’s stock and saw the singer return to Glastonbury in June 2007 as a headliner on the Pyramid Stage alongside the trendy indie bands Kasabian and The Arctic Monkeys. Backed by a five-piece rhythm section flanked by three horn players and two sharp-suited male backing singers, Winehouse took to the stage and – against the backdrop of dark clouds and falling rain – kicked off with the uptempo “Addicted,” a song detailing her love affair with “weed.”

That number was just one of ten songs from Back To Black included in Winehouse’s set; the album’s hit title tune and the Motown-channeling “Tears Dry On Their Own” received huge roars of recognition and approval from the “Glasto” faithful but the most affecting performance came in the shape of the outstanding self-penned ballad, “Love Is A Losing Game,” for which Winehouse later won an Ivor Novello award. She prefaced her performance by saying: “This is a song I wrote when I didn’t believe in love and then I started listening to the darkness a lot more.” Her rendition – perhaps affected by her boyfriend Blake Fielder-Civil’s being in prison at the time of her Glastonbury performance – is deeply poignant, revealing a core of fragile vulnerability that lay behind the singer’s brash demeanor.

Amy Winehouse - Love Is A Losing Game

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Elsewhere in her set, Winehouse sprinkled in some arresting cover tunes. A couple of them were associated with the UK two-tone group The Specials: the Coventry band inspired Winehouse’s vibrant revamp of their tune “Hey Little Rich Girl ”as well as her ska-style retread of Toots & The Maytals’ “Monkey Man.” She also reworked soul man Sam Cooke’s 1961 hit “Cupid” using a jaunty reggae groove; Winehouse had previously recorded the song for a BBC radio session and was performing it live for the first time at Glastonbury.

Winehouse closed her set with another cover; a song she described to the audience as “one of my favorite tunes from last year” – “Valerie,” as recorded by the Scottish indie band The Zutons. Only two weeks before her Glastonbury appearance, Winehouse’s producer Mark Ronson had released a solo album called Version that featured her as a guest artist on a soulful repurposing of “Valerie”; it would take the UK singles chart by storm in October 2007.

Winehouse played Glastonbury again. But this was, by far, her best. Live At Glastonbury 2007 is a recording that undoubtedly adds extra luster to her legacy, revealing the London chanteuse as one of the most magnetic and compelling live performers of her generation.

Listen to Amy Winehouse’s Live At Glastonbury 2007.

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