Icon Aughts :: Amy Winehouse and Lil’ Wayne: The Inkwell

Round 3 of “A Dime, A Dozen” brings us to the tatted – but oh so talented – tandem that is Amy Winehouse and Lil’ Wayne: The Inkwell.


Seemingly limitless, infinite, amounts of ungodly God-given talent flow through the veins of these two. Amy and Wayne are those kids in the corner who your parents warned you about – but didn’t need to because they were out of your league anyway, in their own special way.

Amy Winehouse: Amy, Amy, Amy… if Lady sang the blues – this one soaked in them. Winehouse’s first album, Frank, saw a 4 year stint between its 2003 UK debut and its 2007 US release; in the time between, Winehouse didn’t sail across the pond – she swam the blue Atlantic, removed the skepticism from British soul, and brought artistry to a world in the midst of the red hot celebrity. Never had our generation been introduced to such an aged fresh sound. Amy single-handedly brought us back to the Jazz Age. The world wasn’t Winehouse’s stage this decade – it was her speakeasy. Winehouse’s atmosphere was pop’s antithesis: overtly underground, drug-addled, authentic, counterculture, apathetic to everything but the art, forever in a harmonic haze – and a microcosm of a society, hidden in plain view.

2003’s Frank was just that – a no-nonsense tale of twenty-something love – of course, we all know, it was far more than that:

Drake says you can’t bring the future back, but when Winehouse asks of herself in 2003’s Frank: “Where’s my moral parallel?,” she defied that theory. Back to Black was the fateful answer –– the artistic masterpiece, and beautiful disaster –– but as it preceded the U.S. release of Winehouse’s true debut, pre-“Rehab”-Frank became the answer to its own question.

Keep in mind that our one-track-mark-and-mind culture first took note of the songstress in 2005, though, when she brought us Back to Black:

Where BtB was the assumed anti-rehab anthem, it rehabilitated a dead medium. A drug is anything taken to alter one’s current state of being. Where BtB reiterated our current state as a generation, it was also the escapist drug that true music can’t help but be, and yet the detox to the industry that forgot its roots.

While Paris, Lindsay, Mary Kate, and Co. slurred and stuttered over post-rehab statements, Amy said point blank: I won’t go. This foreigner felt so familiar – and that is why she is so iconic. Geographically, ethnically, musically, personally: we had never felt so innately connected to someone so human, yet so distant and unknown. She embodied our culture: immersed in the bright lights, but forever shielding ourselves in lieu of the intimacy of a nocturnal veil. The freaks no longer came out at night, the everyman freed themselves there. The moonlight was our sunlight, it fed and nourished our inner beasts. The world said our behavior was wrong, but it was a world of sub-prime lenders, warmongering politicians, backdoor lobbyists, and neo-conservative wolves in sheep’s clothing – or pseudo-emperors with none at all. Amidst a distorted reality of moral dichotomies we live in a comfort zone of taboos – and for the first time we had someone tell our tale; when Puritanical America was shining a fluorescent artificial light on the country, Winehouse brought us back to reality and Back to Black.

Her conviction, her authenticity, her truth was so desperately needed this decade. She was the anti-autotune embodied: “Fxxk the fluff: I don’t wear makeup, I wear the same ballet flats everyday and everywhere – if at all, I take drugs, I take the blame, I take the mic, I’m the un-airbrushed face that has nothing left to give; I’m not a blemish on the general purity, I’m the rule and not the exception, and I am fresh because I am giving you the grit that you refuse to look at in the mirror – on the television, in the newspapers, in the offices (Oval included), in your home – every morning. It is what it is, and I am what I am: what about it?” She had no ulterior motive. She was so, so very real. She made us look at ourselves again; and though we denied it, we couldn’t deny her.

Then, there is the art. She croons in a way that makes doves cry. Winehouse’s melodies billowed like smoke christening our speakeasy. There’s nothing technical, “industry,” studio, or clean about Amy’s music – which is why it is beautiful, dirty, rich.

Lil’ Wayne: If we are Young Money, he is our older brother who just got their bachelor’s degree. More importantly – especially given this of all decades – though, Wayne is New Orleans: period. He is that Southern off-center, raw, artistic, eccentric, culturally rich, worldly, weathered, worn, eternally young – but forever established, embodiment of the joie de vivre. This decade we had a hub, a microcosm, a timeless capsule of a culture seemingly forgotten – in 2005, we let it sink. This decade we had a materialistic, money-hungry, maven christen the culture with the cries of bling-bling – in 2005, that fireman lit the fuse. Brownie did a helluva job; but Wayne rose Hell to bring NoLa back.

To go over Wayne’s discography of mixtapes alone this decade would be like going over each pair of Hammer’s parachute pants, or GaGa’s wigs: iconic individually, but arguably more iconic as a collective – and more easily summarized. From Droughts to Dedications – and everywhere outside and in between – Wayne brought the underground up top. Even the now-well-mossy Rolling Stone began listing the “Top Mixtapes of the Year:” check – mate, and please.

Tha Carter and Tha Carter II, Star Wars and The Empire Strikes Back: the formal foot-in-the-door, and the solidified foothold. Both sets are cultural phenomena, both interplanetary displays transposed amongst mere Earthlings – giving a glimpse of a distant artistic alternate atmosphere. Then the Jedi returned; then Tha Carter III landed; then the hat-trick – the trilogy, the trinity. Mainstream reception? MTV asked a certain t-shirt wearing country-pop figure at the 2008 VMAs who’s performance they enjoyed the most, she said Lil’ Wayne’s as when he came on stage a “glow” came off him because “this was the man who sold 1 million copies in a week.” 1 album, 1 million copies sold, 1 week, 2008: said. He is the last person this decade to accomplish such a feat – and quite likely ever. Wayne may be the first man to legitimately translate hype and hearsay – anticipation built from perfectly planned mixtape releases – into hard stacks, cash, and sales.

Backed by his Young Money conglomerate – or rather vice versa – Wayne is the second coming of the Carter: Shawn Carter. He hustled his way to the top and kept that hustler mentality with a new-found business man mindset. He set a new blueprint for a new generation – as the peer, not the patriarch.

Amy Winehouse and Lil’ Wayne: an endless well of inked talent. This tandem has scribed some of the most memorable and reflective tracks of the decade and our generation. They represent our raw selves, the most authentic representations of Pop. Wayne took the ice off for a minute and got dirty – so did we; Amy went back to black – frankly, so did weand again. In an era of perception blinding and veiling reality – these two were our moral parallels.


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