Amy Winehouse’s 10 Best Deep Cuts

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It still comes as a shock that seven years ago today, we lost Amy Winehouse then at the top of her game, at the age of 27. Amid the heartbreak that surrounds this date, one sentiment holds true: the singer’s legacy of bringing modern, sexy blue-eyed soul back into the mainstream will not be forgotten.

When Winehouse first burst onto the scene, the scrappy lass with the smoky, cigarette-coated pipes became emblematic of the streets of North London in the same way Édith Piaf became symbolic of Bellevue. Some would call it sacrilege to even compare the two, but to see an artist so consummate rise from the streets, hit it big and be as disoriented by fame as she was is not an isolated incident: Winehouse’s effervescent life was marked by tragedy and by struggle, too… But let us not make the mistake of leaving out the music.

On the anniversary of her passing, celebrate the legacy of Amy Winehouse by digging into ten of her best deep cuts, below.

  • 1

    “In My Bed” (AOL Live Session), Frank

    This particularly brassy cut from Winehouse’s flawless first effort might be missing the jazz flute that makes the studio version what it is, but it more than makes up for it with a brass section matching the singer’s timeless voice. Early Amy already had her own bravado — a toughened jazz star with all the elegance of the old divas. Pay close attention to her eyes as she sings, “The only time I hold your hand / Is to get the angle right.”

  • 2

    “What Is It About Men,” Frank

    Probably the most relatable ode to doubts brought about by the usual suspect: men. This heavily underrated track from Frank sees Amy playing with the themes of heartbreak, sex, and self-loathing that would go on to mark her entire discography, with nods to the loneliness that would ultimately define her.

  • 3

    “Some Unholy War,” Back to Black

    A torch song for a lover fighting far away, Winehouse sings about standing beside her beloved, patiently waiting for the day that he’ll come back. One of <em>Back to Black</em>‘s briefer moments, it still encompasses the ardor that makes up the rest of the album, and even works as a slight sorbet to the heavier songs at the end of Winehouse’s second and final record.

  • 4

    “Me and Mr. Jones,” Back to Black

    How this one was never released as a single is completely beyond us. Later revealed to be about Nas, this slow-swinging song about loyalty is signature Winehouse: sweltering, seductive and brassy, bemoaning a love gone wrong. Still, nobody stands between her and her man.

  • 5

    “Cherry Wine,” Nas’ Life is Good

    The sexual and emotional chemistry Winehouse bemoans on “Me & Mr. Jones” is also palpable on the fourth single off Nas’ 2012 record. Written fresh after his divorce with Kelis, it can definitely be read as a bold move to include Winehouse of all people on the record. “Where is the man who is just like me,” Winehouse wonders, delivering as much pain as passion. Then again, that was most definitely her preferred currency.

  • 6

    “You Know I’m No Good (feat. Ghostface Killah),” Back to Black

    One of Back to Black‘s most iconic tracks gets a makeover à la Ghostface Killah, and we’re not entirely mad about what he adds to the track even if it feels like it should remain untouched. There’s just something about Ghostface rapping about diamonds and the decadence of New York over jazz trumpets from the other side of the pond.

  • 7

    “Between the Cheats,” Lioness: Hidden Treasures

    A swing-influenced song of sorrow and one of the unreleased tracks off Lioness, this deep cut paints heartbreak in a danceable, sunlit way. A beautiful track that we could easily see on Back to Black, the fact that it hit the world posthumously was an arrow to the heart.

  • 8

    “The Girl From Ipanema”, Lioness: Hidden Treasures

    This cover of the bossa nova classic more than holds its own alongside the original on Lioness. Adding a bouncy energy to the more seductive original, Winehouse’s take on this standard is one of her earliest known recordings. Long-time fans will recognize a less brassy Amy, and will appreciate her successful early attempts at scatting.

  • 9

    “Wake Up Alone (Original Recording),” Lioness: Hidden Treasures

    Much slower and guitar-oriented than the single released on Back to Black, the demo for what would become one of Winehouse’s most painful heartbreak anthems feels even more tender and sensitive. If you listen closely, you can hear the faint crackles of a voice yet to discover its own power.

  • 10

    “Body and Soul,” Tony Bennett’s Duets II

    Winehouse’s last recording is a tear-jerking duet with none other than legendary jazz singer Tony Bennett. The slow track, accompanied only by a piano and her brass-laden voice alongside his smooth, near-talk delivery, is a heartbreaking reminder of what we lost. It’s only fitting that a star who burnt out so fast be said farewell to with a song as slow and peaceful as this one.

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