Amy Winehouse was arguably one of the decade’s strongest, most nakedly expressive singer/songwriters. Just 27 when she passed away July 23, 2011, Winehouse was a five-time Grammy winner whose multiplatinum Back to Black (2007) reinvigorated a (mostly) British remake/remodel of American soul music. The trend continued with the ubiquitous ascendancy of Adele, herself a progeny of a rich lineage of White (mostly Brit) artists including Annie Lennox, Lisa Stansfield, George Michael, and the late Teena Marie—all of whom easily crossed over to Black audiences.

Though Back to Black was her first U.S. release, Amy’s sophomore album was actually the follow-up to 2003’s Frank. Available through iTunes, Frank was a jazzy, smartly drawn collection which garnered Winehouse fevered attention and praise from the public, press and music industry. All of which meant that by the time of her two sold-out New York City shows in January 2007, the working class Jewish girl from North London was a front-runner in the Next Big Thing (U.K. division) sweepstakes.

The honor was dubious when one considers the status of hyped today, gone tomorrow singers like Craig David and Joss Stone. Frank’s appeal to Anglophile soul heads wasn’t surprising. The years have shown that when it comes to reinterpreting American R&B, the Brits have a darn good track record. But Winehouse’s advance team also included hip-hop fans.

A scant three months before Back to Black’s release, Winehouse teamed with Ghostface on a sinewy, hydro-fortified remix of her bad girl anthem, “You Know I’m No Good,” and it was that partnership—combined with the admiration and strong support of, among others, Mos Def and Jay Z, both of whom attended the NYC shows—that caught the attention of the rap demographic. Till then, the strategy had gone untapped when it came to breaking U.K. pop/R&B.

Winehouse and Yasiin Bey (f.k.a. Mos Def) went way back; she often mentioned they were planning to record a joint jazz album. As for Jay, the then president of Def Jam had unsuccessfully tried to sign Winehouse to the label. Maybe as a consolation prize, he appeared on a remix of Winehouse’s top 10 smash, “Rehab.”

Co-produced by Mark Ronson and Salaam Remi, Back to Black sidestepped the dreaded retro tag by bolstering its pronounced R&B sway and girl group dynamics with hip-hop’s kick and attitude. On the finger-snapping “Addicted,” Winehouse mused unabashedly about her love of weed. While “Me & Mr. Jones (F*ckery)” (the title a reference to her crush on Nasir Jones) found Winehouse righteously, profanely beating down an errant lover who made her miss a Slick Rick show.

Both of its time and yet destined to be timeless, Back to Black found the sweet spot between Motown, Phil Spector, passion and pathos. For all of its clear musical touchstones, it remains a remarkably original album.

I interviewed Winehouse in March 2007, on the day Back to Black hit stores. (Yes, folks still bought CDs six years ago.) Despite her reputation as a hell-raiser, in person Winehouse was shy and uneasy, loathe to talking about herself but eager to discuss music. And because the magazine I was writing for was aimed at a hip-hop audience, the conversation moved to what hip-hop meant to her. The singer had come of age loving Queen Latifah, Salt-N- Pepa, Rah Digga and Lil Mo, and when she was 12, an older cousin took her to see Lauryn Hill in concert. (Years later, Winehouse often performed Hill’s “Doo Wop (That Thing)” at her own shows.) Speaking to those formative years, Winehouse remarked, “I’m really lucky that I’m of that generation that when [Hill’s] album came out, we were young. We were growing up.”

For obvious reasons, comparing Amy Winehouse to Miley Cyrus is laughable. But as the latter’s recent twerk-a-thon debacle so painfully demonstrated, stakes continue to be high for White artists referencing so-called urban culture or Black music. Because no matter how pure their intentions, there’s always the risk that when an artist pays homage, it can be repositioned as tacit permission to step over a line (blurred or otherwise) and enter territory that could—and possibly should—be off limits. One false or insensitive move, and appreciation can devolve into co-opting, or karaoke. 

Much as it had been with Stansfield, Marie, et al., Amy Winehouse never tried to be something she wasn’t. If, as a handful of detractors offered, she sounded Black, I’d argue that what they might have meant, or should have said, was that Winehouse found the truth, and articulated the emotion and depth of experience that’s ofttimes associated with Black music. And audiences across racial lines heard that respect and Winehouse’s pain, and responded. It’s part of the reason why hip-hop appreciated her.

Amy Linden is a pop culture writer and educator whose work has appeared in Vibe, The New York Times, XXL and elsewhere. Follow her on Twitter @notfornothin59.