Amy Winehouse is an artist notorious for her candour. From poking fun at her own misfortune to writing songs that laid bare every insecurity and shortcoming in her own life, she appeared to prioritise (sometimes caustic) honesty over insincerity. It was the antithesis to what she saw, in the early 2000s, as a British music scene filled with fakery. What’s more, she did it all with a laugh: As she once said, adding a punchline to a song was a means of distracting from life’s darkness. Proving this point is Winehouse’s debut album Frank. Filled with the same humour, vulnerability and overly confident postering found in a drunken fight outside a nightclub, it’s a raw, biting and tear-stained snapshot of heartache and the pangs of young womanhood. Winehouse isn’t shy about asserting herself. Not only is this a jazz record (the album opens with Winehouse scatting), but it’s a jazz album that’s crafted by a someone who wants you to know she grew up in the musical melting pot that is London. Awash with hip-hop beats (“You Sent Me Flying”), hazy neo-soul (“Help Yourself”), strobing trip-hop production (“In My Bed”), street-smart pop hooks (“October Song”) and smoky suspended chords (“I Heard Love Is Blind”), Winehouse ties together these seemingly disparate references with her timeless after-hours drawl. That iconic voice, along with her impeccable sense of phrasing, also provides the perfect vehicle to deliver her cutting lyrics. On Frank, she eyerolls at weak men (“Stronger Than Me”), defends a night of infidelity with a wry smirk (“Don’t overreact/I pretended he was you,” she pouts on “I Heard Love Is Blind”) and lovingly mocks party girls on “Fuck Me Pumps” (“Never miss a night/’Cause your dream in life/Is to be a footballer’s wife”). Scrape back the bravado, though, and you’ll find Winehouse’s fraying edges. On “What Is It About Men” she skirts familial infidelity, questioning whether her own poor relationship decisions are hereditary (“History repeats itself/It fails to die”). The gut-wrenching “Take the Box” recounts, in almost painstaking detail, Winehouse returning a box of her ex’s belongings (“The Moschino bra you bought me last Christmas/Put it in the box, put it in the box”). And “You Sent Me Flying” is tortured with doubt and the ache of rejection by an older man, Winehouse admitting, “I’ve never hated myself for my age so much.” Such directness proved too much for her, though, and Winehouse once said that she had never even heard Frank in full because it hurt too much to listen back to. She would later also criticise some of the creative decisions she said were forced upon her (she found the synthesised string section on “Take the Box” particularly egregious). Given her disdain for the album, it was perhaps lucky that her follow-up, Back to Black, was the more commercially successful of the two, although the subject matter of that album clearly took an emotional toll. Still, despite Winehouse’s complaints, Frank remains as scrappy, piercing and desperately funny as it was when it was released.

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