“I love all kinds of music, but when it comes to writing, I’m especially drawn to Amy Winehouse because you feel like you’re listening to a piece of her life. Even if she’s singing about things that haven’t happened to you, you identify with it. Maybe that’s why I write this way. I’m not an abstract girl; I go straight to the point.”
Those were the words of Olivia Dean, the rising singer who has been selling millions of copies lately and was pegged as a Grammy favorite for 2027, when she was just starting out in May 2020. In another interview from 2021—two years before her debut album—she echoed roughly the same sentiment, adding: “I don’t think Amy ever intended to be a pop star. She just wanted to be herself. She had a genuine love for music. It’s clear in her songs that she used it as a form of therapy.”
These recent statements come from a series of short conversations posted on Amy’s YouTube channel, where people as varied as Nile Rodgers, Yungblud, or Jamie Cullum offered their take on her legacy. Given the growing significance of her story in recent times, it’s also worth noting the early contribution of a then-unknown Lola Young, who, very much in her style, praised the sense of freedom Amy inspired: “Watch her interviews and you can see she rejects being anyone other than herself, which is rare, because when you’re an artist, there are plenty of people behind the camera telling you what you should say, what dress you should wear—basically who you should be. She said things no one else did. She was confident, striking, incredibly funny, brilliant, and intelligent.”
Comparisons to Amy have been particularly painful for RAYE, who confronts them at the opening of her latest album, “This Music May Contain Hope,” another entry favored for the 2027 Grammys. As she described in a Billboard interview, the comparisons have genuinely angered her—not because flattery eludes her, but because of all the “hate” she has faced from those who insist she’ll never be Amy Winehouse, a pressure and hatred that, in her view, echoes the harsh scrutiny that Winehouse faced in life.
Adding to the sense that Amy’s influence remains potent is the Rolling Stones’ new version of “You Know I’m No Good,” alongside the unusual popularity of impersonators and tribute performances—some of the impersonations are chilling—suggesting that Amy Winehouse’s legacy is more vibrant than ever. And even news about her estate continues to surface. Recently her father lost a lawsuit against two of Amy’s friends—her stylist Naomi Parry and her housemate Catriona Gourlay—who had auctioned off 155 items the singer had gifted to them during her life: clothes, ballet shoes, handbags, earrings, and makeup. Mitch argued for a share of the proceeds, claiming he hadn’t been informed about the auctions. He never seemed to have enough.
Perhaps that explains why, on October 23, a new reissue of “Back to Black” is arriving, at a moment when there might be little left to add to a record that has seen numerous “deluxe” editions from the very start and has been reissued several times. At some point one must accept that this woman could only produce two and a half albums, painful as that sounds.
Or perhaps it was inevitable that Universal would mark the 20th anniversary of one of the century’s masterworks, a record that sold up to 25 million copies. No, we’ve never encountered another artist as free, singular, and unmistakable as Amy. It isn’t merely the beehive updo, the sometimes exaggerated pin-up line, or the images—often infelicitous or hilarious—still wandering through Camden in practically nothing but a bra and underwear. It’s that hearing her voice means continuing to confront, across its full spectrum of emotions, the pain of “Back to Black,” the jealousy of “Me & Mr Jones,” the optimism of “Tears Dry On Their Own,” the hope she embodied in “He Can Only Hold Her” (Olivia Dean’s favorite), the resignation of “Wake Up Alone,” the addiction of “Rehab,” and the sensuality of “Just Friends.” She was influenced by Ella Fitzgerald, Dinah Washington, or Ray Charles, but she gave those classic sounds bold, fresh, sexually fearless, and irreverent, all wrapped in her uniquely poetic voice. “Love Is a Losing Game” is one of the few songs she wrote entirely by herself. Expressions that have always felt like band tee sayings, such as “you don’t mean dick to me” or “sniffed me out like I was Tanqueray,” still bring a smile.
The forthcoming reissue will feature the original album alongside a wealth of demos—four of them previously unreleased—plus the Paradiso concert in Amsterdam from 2007. There are new photographs from the same team who shot the original session, but perhaps the most intriguing content will be the written notes by producers Mark Ronson and Salaam Remi, among others. Someone recently commented on Popsquare, “The older I get, the more I realize how young Amy was when she died.” It is within this shared sadness that we still feel for her absence that we will perhaps find a measure of comfort.
And yet, although Amy’s legacy remains vivid and her fans are now enormous on streaming platforms (Back to Black nears 2 billion plays), her current streaming statistics don’t always reflect the magnitude of her talent. She sits at a modest 384th place among the world’s most listened-to artists. In Spotify’s Global Top 200, you’ll find three tracks by the late Michael Jackson, four vintage Coldplay hits, eight songs by Bruno Mars (mostly from catalog), three by Arctic Monkeys, two by Radiohead, one each by Oasis, Nirvana, Evanescence, and The Police—yet never any Amy Winehouse. And when a track does appear on the British charts now and again, is it always the Valerie cover?
Those of us who adore Amy’s music never seem to have enough, especially in an era when it feels like only older songs are played. It seems we still await the perfect synchronization with a TV series or film, the timely TikTok trend, that would propel Winehouse back to the top—her position that she held so often between 2006 and 2011, before her passing.
