Up Close and Personal

It's not hard to pick singer-songwriter Andra Day out of a crowd. With her signature '50s-style beehive, slick makeup, and oversize hoop earrings, she's a blast from the past. But there's more to Day than meets the eye. Her arresting alto, which can shift effortlessly from a raspy falsetto to a full-throated belt, has drawn comparisons to Etta James and Nina Simone. "At first I felt pressure to write and sound more like a pop singer," says Day, 30. "But I'm a jazz vocalist. My idols are singers like Billie Holiday and Erykah Badu because there's no gloss on what they do. I've always wanted to be a woman who isn't afraid to tell her story."

On the Move

Six years ago, Day spent her time hustling from job to job—running a paper route, manning the desk in a video store, working at a taco joint—all in an effort to support her music career. "I was willing to do whatever it took," she says, "even if that meant scrubbing apartment floors by day and gigging at night." Then Stevie Wonder's wife caught Day singing at a strip mall in Malibu and recorded it on her phone, which led to a surprise call from Wonder himself. "It's a blur," says Day, "but I do remember him telling me I was talented!" Wonder soon introduced Day to a producer who encouraged her to post her takes on popular songs (like an acoustic version of Eminem's "Lose Yourself") online. A few months later, she inked a deal with Warner Bros. Records. "I spent years trying to find producers and put down tracks," says Day. "That time let me grow—and gave me a lot of material to work with."

Hitting the High Notes

Less than three years later, Day's debut, Cheers to the Fall, is a soaring compilation of inspiring power anthems and jazzy ballads. "The record is a salute to failure and redemption," she says. "It's my testament that if you fall, you will get back up." Day's own vulnerability shines through on tracks like "Gold," where she laments cheating on an ex. "It's never easy to talk about guilt, but finding the courage to tell my story was freeing," says Day. "This album is my autobiography—told in 13 soul tracks."

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