Born and raised working-class in New York City’s outer boroughs, Lauper was too stubborn and strange to succeed at school socially or academically. Her parents, both casually musical, divorced by the time she was five. She and her older sister Ellen spent the rest of their adolescence, in Lauper’s words, “dodging pedophiles and the crazy folks,” including their stepfather and grandfather. Cyndi left home at 17 to live with Ellen on Long Island, where she worked as a “hot walker” for racehorses at Belmont Park, singing Hare Krishna mantras into their ears to calm them down. In her free time, she auditioned for cover bands that traveled the Long Island bar circuit. By 1974, she landed a gig as a backup singer, and was soon asked to step up for brief solos: “Lady Marmalade,” “Tell Me Something Good.” Once it became clear that Lauper’s voice worked best front and center, she became a permanent lead.
Cover bands were an ideal proving ground for Lauper. With her four-octave range and irreverent sense of humor, she reimagined the pop canon, imbuing it with her particular sense of wonder toward the world. Just as she would after finding stardom years later, she twisted other peoples’ words to her own will, cracking songs open to reveal new meanings beneath their popular interpretations. It’s hard to hear her sing Jackie Wilson’s “Baby Workout” and miss how enthralled she seems by her own delivery, adding extra vocal runs as if it’s as easy as breathing. And Lauper’s particularities as a performer offered a counterintuitive kind of universal appeal: If this highly unusual woman with a neon orange buzzcut who spoke like a streetwise Minnie Mouse could convincingly inhabit music from Jefferson Airplane, or the Rolling Stones, or Prince, then maybe those songs were for everyone.
Still, she aspired to more than singing other people’s hits. “If you sing ‘White Rabbit’ one more time, just shoot yourself,” she remembered thinking at the time. By the end of the decade, she had formed her own group, the rockabilly-inspired Blue Angel, with John Turi, a saxophonist from her cover band. Critics loved them; they toured with Hall and Oates and the Human League. Lauper was the kind of singer everyone wanted to sign as a solo artist—“Like Chrissie Hynde and Deborah Harry, Lauper possesses the vocal ability to make her stand out,” Billboard raved at the time—but she held out until Polydor agreed to sign Blue Angel as a full band.
It didn’t quite work out: After a batch of expensive failed demos, a subsequent lawsuit, and a debilitating vocal cyst, Lauper began the 1980s bankrupt and out of the music industry. She started working at Screaming Mimi’s, the Manhattan costume vintage store where she honed her singular sense of style, combining layered neon skirts with punk’s jagged industrial edges. She hired a vocal coach and connected with David Wolff, who became her longtime manager and boyfriend. By 1983, she found herself in the studio with Turi and producer Rick Chertoff, recording her first album under her own name.
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