Amy Winehouse was one of those once-in-a-generation artists who rerouted the direction of pop music. 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, Frank’s jazzy torch songs (“You Sent Me Flying / Cherry,” “Take the Box”) and chilled funk atmospheres (“In My Bed,” “F**k Me Pumps”) only teased at the feisty character she would become. Winehouse’s outsized persona got the space to fully flourish on 2006’s Back to Black, which transformed Winehouse into the consummate anti-diva, exuding a raw, unfiltered authenticity that was at once cheekily risqué (“Rehab,” “You Know I’m No Good”) and emotionally shattering (“Love Is a Losing Game” and the devastating title track). Sadly, the album 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 to guide artists like Adele, Janelle Monáe, Sam Smith, and Lana Del Rey to pursue their own retro-modernist visions.