Taylor Swift & Amy Winehouse: Comparing the Legacies of Two 21st Century Pop Icons

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Taylor Swift and Amy Winehouse.

It felt strange last week to celebrate both the tenth anniversary of Taylor Swift and Back to Black -- two of the most impactful breakthrough albums in 21st-century pop -- within days of one another. Taylor Swift's debut album and Amy Winehouse's first crossover success hardly feel like they're part of the same musical universe, let alone the same exact calendar region. Taylor Swift used Taylor Swift as a springboard to becoming TAYLOR SWIFT, achieving such massive commercial and artistic success that today the album feels quaint and low-stakes by comparison. Meanwhile, Amy's inability to follow up Back to Black before her tragic death in 2011 gives the album an emotional heft and totemic status that seems to only get weightier in the years since.

However, 10 years later, the two albums stand as most of our introductions to two defining artists of the decade to follow — even if their legacies ended up skewing in almost diametrically opposed directions. As she rose from the relatively humble country beginnings of her debut to the monolithic pop of Red and 1989 (with assistance from cohorts like Max Martin and Shellback) Taylor Swift has come to define the sound of modern top 40 -- somewhat ironically, given the purportedly throwback leanings of her latest (and fastest-selling) LP. Meanwhile, Amy Winehouse's breakout represented a sort of updated soul-pop classicism, paving the way for similarly retro-leaning artists like Duffy, Bruno Mars and Adele -- not to mention the eventual U.S. takeover of BTB co-producer Mark Ronson -- in the process.

In method and ideology, the two artists were similarly contrasting. While Swift emerged in the mainstream as a star-struck high school student, she quickly displayed business, media and artistic savvy well beyond her years, with a spotless record (at least until very recently) of shrewd and inspired decision-making, in everything from her live packaging to her album rollouts to her choices of musical collaborators. Winehouse, on the other hand, was as messy and uncalculated as any star performer of her generation, giving emotionally sprawling interviews, getting in trouble with the law, and suffering through a very public battle with substance abuse, which would ultimately lead to her demise. "Taylor Swift is everything Amy Winehouse wasn't," a headline from U.K. publication The Express proclaimed succinctly (if excessively self-righteously) in 2015.

Evidence suggests, however, that the two artists shared a sort of affinity during the same period in pop's mainstream. During a London live date in 2008, Swift actually covered Winehouse's signature hit "Rehab" solo on guitar, a rendition that understandably lacks the grit of Amy's lived-in original, but which still makes a clear connection to the song's spiritually adrift emotional core. A few years later, Winehouse was snapped heading to Abbey Road studios, where Taylor Swift was about to perform for BBC 2's In Concert series. ("One might not necessarily expect the former bad girl... to show support to America's most pristine pop-country superstar," stated an MTV item on the photo at the time. "But Amy Winehouse was anything but predictable.")

Despite their myriad fundamental differences, it's not totally surprising that Taylor and Amy would be fans of one another's music, given that at heart, both of them were pop obsessives. Swift may have idolized James Taylor, Alanis Morissette and Tim McGraw, while Winehouse's north stars were Frank Sinatra, Ronnie Spector and Nas, but both artists internalized the greatest lessons of top 40 history and funneled them into new songs that were just as raw and true as the classics of their heroes. It's not hard to imagine Winehouse relating to the bloodiness of a Swift breakup song like "Dear John" or "Forever and Always," while it's equally easy to picture Swift losing herself in the open despair of "Love Is a Losing Game" or "Wake Up Alone." At the end of the day, both artists were really just great singer-songwriters.

It especially hurts to hold Taylor Swift and Back to Black back to back. If things had gone differently in her personal life, could Amy Winehouse have evolved, expanded, and eventually taken over the way Taylor Swift did? Maybe not -- almost certainly not in the same way -- and it may not have been what she wanted in the first place. But removed from the cruelties of top 40 and the world at large, a decade later we can listen to these albums and remember when Taylor Swift and Amy Winehouse were both newly discovered musical sensations on an even playing field -- each with a handful of some of the best pop songs we'd heard that decade, and likely happy to have one another as company.