Cyndi Lauper Illustration by João Fazenda

“It all kinda started a long, long time ago,” Cyndi Lauper said the other day, discussing her commitment to end homelessness, especially among L.G.B.T. youth. Lauper was looking out on the Hudson River from Jane Street, the day after the season’s first snow. A long time ago was 2007, when Lauper was doing a photo shoot for Interview on the West Side piers. “There were a lot of young people—Hispanic, African-American, one East Indian transgender male—and they were homeless, because they had been thrown out,” she recalled. “I’m a mom. It’s not easy. Kids don’t come with a receipt so you can bring them back if it’s not working out, you know?”

Shivering, she went into the Jane Hotel and, in her unmistakable Queens drawl, ordered a hoawt toawddy. She took off her hat to reveal a pinkish pixie cut, and underneath her coat were a biker jacket and psychedelic purple pants. Seeing those runaways on the piers, she continued, inspired her to co-found the True Colors Fund, which supports fellowships for homeless kids and tools for shelters to assess their L.G.B.T. inclusivity. (On December 8th, she will celebrate the fund’s ten-year anniversary with her annual “Home for the Holidays” benefit concert, at the Beacon Theatre.) Gay and transgender youth, Lauper noted, are a hundred and twenty per cent more likely than their peers to experience homelessness. “Like hoawtcakes they get thrown out,” she said, speaking out of one side of her mouth, as if the other held a cigarette.

Lauper herself was briefly homeless during her teens. She left her mother’s house, in Ozone Park, when she was seventeen, after she caught her stepfather spying on her in the bathtub. Taking a toothbrush, an apple, and a copy of Yoko Ono’s “Grapefruit” with her, she crashed at her sister’s place, in Valley Stream, on Long Island, which they shared with a friend called Wha. Lauper was already “freakified,” she said—she wore a seashell necklace as a headband—but she managed to find work as a receptionist for Simon & Schuster in Manhattan. “I was like Gal Friday the Thirteenth,” she said. “No matter how hard I tried, I kept falling asleep reading the mail.” Other ill-fated jobs followed: waiting tables at IHOP, hot-walking horses at the Belmont Park racetrack, selling shoes at a mall. Some nights, she would clean up at a Hare Krishna temple in exchange for meals, but she stopped after the members told her that the women there ate in a separate room after serving the men. “I said, ‘Hey, I’m Sicilian! I left that life. I ain’t goin’ back.’ ”

She bought a tent and brought her dog, Sparkle, to Algonquin Provincial Park, in Ontario, where she spent two weeks camping out and drawing trees. Her sister mailed her her unemployment checks. She caught a “magic bus” back home and moved in with her mother, who had divorced her stepfather. She panhandled in the Village and busked on her guitar, though she knew just two Joni Mitchell songs. Still too young to sign a lease in New York, she got a ride to Vermont and wound up at a youth hostel in Burlington. “That’s when I really saw homelessness,” she said. The welfare office helped her get a job at a kennel and rent an apartment, where she had dreams of Jimi Hendrix telling her, “When are you coming home?”

Through the hostel, she met a fifteen-year-old runaway named Ann Marie, who was dating a much older man. Lauper took her in. “I thought, Maybe I can just adopt her. I’m over eighteen,” she said. “And then I realized that she was a teen-ager, and I would have to provide more than I probably could.” Ann Marie wound up in a juvenile detention center. “She had to euthanize her dog, who she loved,” Lauper said. “The whole thing was so messed up.” Once she moved back to New York, she heard about Ann Marie’s whereabouts in “bits and bobs,” but lost track as rock stardom took over.

In 2011, Lauper helped open the True Colors Residence, a thirty-bed shelter in Harlem for L.G.B.T. youth; a second location, True Colors Bronx, followed, in 2015. “Yeah, the homeless situation gets me,” she went on, buttoning her coat to leave. “Just does. It’s hard to live in the cold. I lucked out. I’m not there. But it doesn’t mean I forgot and that I can’t help—especially kids like Ann Marie, who I failed once. This time I’m not going to fail her.” ♦