The R&B singer’s music and backstory took on a mythical quality when she disappeared from public view. Now a retrospective is retelling her story

Anyone imagining the life of a black transgender woman in the American south of the 1950s and 60s may expect a world of taunts, misunderstanding and fear. Jackie Shane, who lived that life growing up in Nashville, claims she never experienced any of those things. “I’ve never had a problem, not once,” Shane says. “Even in school, the other kids accepted me. So did their parents. There was something about me that drew them.”

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Years later, that something made Shane a highly improbable star, based on a deeply soulful singing voice, and a courtly presence, that drew interest from Motown and Atlantic Records, an invitation to appear on Ed Sullivan’s powerful TV variety show and talks with George Clinton about joining Parliament-Funkadelic. Her music from that period is getting a surprising second life through a compilation of blistering studio and live performances from the 60s compiled by the archival company Numero Group for the new set Any Other Way.

More than five decades ago Shane headlined clubs in her adopted town of Toronto while sporting full makeup, wigs and sequin tops. Her presentation didn’t stop her from performing on television, or from scoring a No 2 hit on Toronto radio with a cover of a soulful song of acceptance, Any Other Way.

The singer – who is now 77 – speaks with a preacher’s belief, filling her conversation with advice and entreaties to “ignore the lies of ignorant people” and to “live and let live”. Shane always knew she was a woman, though others didn’t always identify her as such. “At five years old, I would dress in a dress, hat, purse and high heels and go up and down the block – and enjoy it.”

Shane credits some of her confidence to her grandparents and mother. “They were beacons to our lives,” she says. “They understood me.” That wasn’t always easy to do. “Some adults were afraid of me because I was intelligent,” Shane says. “I thought for myself.”

She proved it in her early musical experiences. Shane first sang in church, where she was placed in the adult choir. Shane began singing secular music at age 13 after hearing a neighborhood boy play blues piano. Entranced, she hung around for hours, eventually banging out drum parts on a chair. The piano player told her she was a natural drummer and asked her to get a set to play. Joined by a guitarist, they became a trio, enjoying local success. “Once we started, the jobs kept coming,” Shane says.

At five​​ years old, I would dress in a dress, hat, purse and high heels and go up and down the block – and enjoy it Jackie Shane

Eventually, racism drove Shane out of the Jim Crow south and Shane moved to Canada, first to Montreal where she met and joined a pumping R&B band led by Frank Motley. They moved to Toronto by 1961, where they began to play the clubs on bustling Yonge Street. Because the bouffant-haired Shane often wore pants on stage “most people thought I was a lesbian”, she says. “One taxi driver said ‘I don’t know why, as pretty as she is, she wears suits.”

Shane never played gay clubs. “I’m an R&B singer, not a mimic,” she says. “I sing the blues. I love the blues. I understand the blues.” Shane not only became successful enough to play Canadian clubs, but to dip back into the States to perform.

But Shane was just as unimpressed by the powerful labels that courted her. Motown representatives came to see her at a Yonge Street club one night. “They had a whole row of champagne buckets,” she says. “They tried to talk to me. But I had been schooled about Berry Gordy taking the entertainers’ money. I wasn’t going to get involved in that.”

Atlantic Records also got the thumbs down. The recordings she did make capture a voice of uncommon soul. Cuts on the new compilation like her covers of Money and Cruel Cruel World reveal a rich and smoky timbre, not unlike Nina Simone’s, as well as a dignified delivery.

Facebook Twitter Pinterest Jackie Shane, who often wore pants on stage. ‘Most people thought I was a lesbian.’ Photograph: Courtesy of Numero Group

Though accepted in the clubs, Shane says she was sometimes hassled by the police in Toronto. “Those creatures on the force, they were gay but will never come out,” she says. “They feel they’ve got to hide, so you should too. They would see me in a motor car with these fine boys and, of course, they’re drooling. They would stop us and try to get these boys to say that I was soliciting. The boys would say you’re wrong. We’re with Jackie because we want to be.”

Shane faced other challenges from her band mates, who often wanted to have sex with her. “I’ve never had a group that didn’t have one member who wouldn’t leave me alone,” she says. “I don’t want you. I will never be with another entertainer or musician – ever!” A member of one group pulled a knife on her and threatened to cut her face. “I told him to make it smooth,” Shane says. “I walked away from that group.”

For a while, the singer based herself in Los Angeles where George Clinton’s band talked about hiring her to be a part of Parliament. (“They had a guy with a diaper on. That’s not my thing,” she says.)

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Shane toured with Etta James for a while, but by the early 70s, the singer found herself increasingly tired of the touring life so, eventually, she moved back to Nashville to care for her elderly mother. To fans, and even old band mates, she seemed to disappear into thin air. Rumors began to circulate that she had been murdered in Brazil, something she finds amusing. In 2010, CBC Radio created a documentary on Shane which couldn’t confirm that the singer was still alive.

Over the last decade, small compilations of Shane’s work came out in Canada but the new set is the first to gain the singer’s approval since 1969. Numero Group A&R man Douglas Mcgowan tracked Shane down through a UK blogger who claimed to be in touch with the singer. Mcgowan spent two years talking to the hyper-reclusive Shane, trying to convince her to finally receive a proper retrospective, complete with liner notes that tell her full story. Only with this release is Shane publicly acknowledging her identity as a transgender woman. In earlier press accounts, her sexuality remained ambiguous. “Jackie’s story rewrites history for people,” Mcgowan says. “It tells young people that some people have been fighting for rights before there were even names for their causes.”

Shane is considering performing again, but has no specific plans right now. In the meantime, she takes pride in her retroactive legacy as a gender pioneer. “People have come up to me and said, ‘Jackie thank you. You made it possible for me to have a life.’ That’s why I was there,” she says. “My whole approach is to get you to go up against wrong. I don’t bow down. I do not get down on my knees. The lowest I go is the top of my head. This is Jackie!”