Amy Winehouse was one of those once-in-a-generation artists who rerouted the direction of pop music and amassed a worldwide fanbase spanning grade-schoolers to grandmas. Born in 1983, the London-raised singer paid her dues as a session vocalist before releasing her debut album, Frank, in 2003. While Winehouse’s uncommonly gritty yet graceful voice made her a UK sensation (earning her a place on the Mercury Prize shortlist), Frank’s jazzy torch songs and chilled funk atmosphere only teased at the feisty character lurking beneath the surface of cocktail-lounge soundtracks like “F*ck Me Pumps.” However, with the help of producer Mark Ronson and Sharon Jones’ brassy backing band, The Dap-Kings, Winehouse’s outsized persona got the space to fully flourish on her Grammy-dominating 2006 sophomore release, Back to Black. Adopting the soulful sound and sassy spirit—not to mention beehive hairstyle—of ’60s girl groups, Winehouse hit upon an aesthetic that was faithfully retro enough to win over Motown-reared boomers, yet possessed a brash, profane attitude (and the tattoos to go with it) that endeared her to hip-hop heads and indie kids alike. Back to Black transformed Winehouse into the consummate anti-diva, exuding a raw, unfiltered authenticity that was at once cheekily risque (as heard in her definitive anti-sobriety anthem, “Rehab”) and emotionally shattering (the eternally devastating title track). Sadly, Back to Black was both her career apex and her swan song—she died of alcohol poisoning in 2011. But if Winehouse’s star burned all too briefly, it left a never-ending vapor trail across the mainstream, allowing artists as varied as Adele, Janelle Monáe, Sam Smith, and Lana Del Rey to pursue their own singular visions of retro-modernism.