It was the summer of love: 1967. A crowd had gathered at the Saphire Tavern on a cool July night. Inside the bar, the air was thick with smoke and the sounds of soul music. One of the most exciting bands in the city was onstage. Frank Motley and the Hitchhikers swung with an irresistible blister of horns, guitar, and percussion. But they weren’t the star of the show that night. No, the crowd wasn’t there for the band. They’d come for the singer.
As the Hitchhikers reached the end of their first song — a raucous instrumental introduction that saw bandleader Frank Motley play not just one trumpet, but two at the same time — the moment had come. “It’s just about that time,” Motley announced to the crowd as the band continued to play, “for the star of our review, ladies and gentlemen: Little Jackie Shane!”
Shane had grown up in the musical mecca of Nashville, learning how to sing in church before becoming a staple of the local R & B scene. By the end of her teenage years, she was friends with Little Richard, and had toured with The Impressions and Jackie Wilson. It didn’t take long for it to become clear that Shane was too good; Wilson’s manager paid her to sit out the rest of the tour — she was upstaging the headliner.
She’d known she was a transgender woman for years: she began dressing as a girl at the age of five; by thirteen, she was wearing makeup to school and came out to her mother. “I was born a woman in this body,” Shane explained many years later. “That’s how it’s always been. I’m not putting on an act. I could not be anyone else if I tried. It would be the most ridiculous thing in the world for me to try to be a male.… What I am doing, there is nothing wrong with it. The way others think doesn’t mean anything to me. I’m not hurting anyone.”
In the end, it wasn’t just transphobia that would drive her out of Tennessee. It was racism, too. Nearly a century after slavery was abolished in the United States, the laws of Jim Crow still made segregation a state-sanctioned fact of life. Nashville might have been one of the musical capitals of the world, but it was also a deeply prejudiced place. The final straw for Shane came when she and a friend watched a group of white thugs on a rampage. The gang chased down a Black man, beat him bloody, and threw him in a Dumpster. Then, they dragged Black passengers off a bus and beat them, too. Shane was done with Nashville. “That’s when I started to look for a home.”
Her first step was to join a travelling carnival, performing alongside a snake dancer, a stripper, and a man who ate glass. When they paid a visit to Canada, she knew she’d found the home she was looking for. “I never felt that good before,” she explained. “I felt so free. I just loved it.” When the carnival headed back south across the border, Shane stayed.
It was while walking through the streets of Montreal one night that she found her new backing group, drawn into a club by the sound of soul music. Inside, she found Frank Motley and his band. Motley was a trumpeter from South Carolina who’d studied under Dizzie Gillespie. His unique ability to play two trumpets at once helped his band book regular gigs on both sides of the border. And as soon as they dragged Jackie Shane up onstage to sing with them, it was clear she was going to be touring with them from then on. “Man, let me tell you,” the keyboardist remembered, “Jackie set that place on fire.”
That’s how Shane would end up in Toronto.
Yorkville wasn’t the only neighbourhood where the city’s conservative facade was beginning to crack. By the end of the 1950s, the Yonge Street Strip had earned a notorious reputation as a land of hard drinking and rock ’n’ roll. It wasn’t for the faint of heart: when The Band got their start playing taverns on the strip, they wore brass knuckles onstage, knowing they might have to fight their way out of the bar after their set was done. But those few blocks between Dundas and Gerrard were also an exciting place for anyone who cared about music.
Motley’s band had been playing gigs in the city for years, and Shane fell in love with it. “You see,” she would later tell the CBC, “one cannot choose where one is born, but you can choose your home. I chose Toronto. I love Toronto.” And Toronto loved her.
As her songs climbed the local CHUM chart, Shane became a familiar face on the Yonge Street Strip. She played bars like the Hawk’s Nest, Zanzibar, and the after-hours club where all the best musicians in the city gathered at the end of the night: Club Bluenote. But it was the Saphire Tavern, just around the corner from the strip, where she was most likely to hold court. Tucked into the ground floor of the old Confederation Life Building (which is still there today at the corner of Richmond and Victoria Streets), the Saphire became Shane’s musical home. She played there for weeks on end, drawing enthusiastic crowds in a city that had never seen anything quite like her before.
“She had a lot of fire,” one of her fellow soul singers, Eric Mercury, remembered. “We had never seen anything up close like that in Toronto. It was like a tornado coming through the place. She was brash. She was the centre of attention. She was authentic; she was for real and she was living her life out loud.”
You can still hear it today: her shows at the Saphire Tavern during that week in the summer of 1967 were recorded for a live album. Half a century later, it’s still recognized as a remarkable record, nominated for a Grammy Award when it was re-released in 2017 along with some of her other songs. After Motley’s introduction, she took the stage — all confidence and grace, wearing a sequined pantsuit and false eyelashes. She was a singer who made every song her own, a performer electric with coiled energy, and an entertainer who knew damn well how to put on a show. In the quieter moments of her sets, her confessional banter allowed her to connect with an audience in an intimate way. Whoever they were — whoever they loved — she could make them feel like they weren’t alone.
When she first started playing at the Saphire Tavern, she made sure her queer fans would feel welcome, talking to the owner to guarantee it. “In fact, I told Mrs. Stone,” she remembered, “‘Look, gay people must be able to come and see me. As long as they come just like everyone else and obey the rules and such, I don’t want anyone kept from seeing me. I want them to come.’ We had an understanding.”
Shane drew audiences both queer and straight, Black and white — as well as everyone in between. And when they ventured inside the Saphire, they found her there onstage, blurring gender lines and talking openly about her sexuality. On the live album, her banter with the audience is filled with references to loving both men and women. “I’m going to enjoy the chicken,” she told the crowd, using a slang term for young men, “the women, the chicken, and everything else that I want to enjoy. That’s how I live. That’s why I’m so happy all the time.” And she took that message well beyond the confines of the Saphire. She played in high schools and YMCAs across the city, and toured communities all over southern Ontario. A curling rink in Scarborough. The town hall in Newmarket. A dance club on the shores of Lake Simcoe. As well as her adult fans, she reached countless queer teens who didn’t have many public role models.
It wasn’t always easy. People gawked and snickered, even in Toronto. “You know,” she explained, “when I’m walking down Yonge Street, you won’t believe this, but you know some of them funny people have the nerve to point the finger at me and grin and smile and whisper.” She often presented as a gay man in drag. Local newspapers wrote columns speculating about her gender; at least one sent a journalist to ask her about it to her face.
Not that she would let that stop her. “So, now listen, baby,” she told the crowd at the Saphire, “when you see Jackie walking down the street, or I walk into a restroom that you’re in, I want you to laugh and talk and grin and point the finger at me because if I ever walked out and they didn’t point and whisper about me, I’d go back in and look in the mirror and stick out my tongue because I thought I was sick or something, I done lost my touch.… Every Monday morning, I laugh and grin on my way to the bank.”
Still, she would never become a major international star. When she was invited onto The Ed Sullivan Show, she refused — they wanted her to take her makeup off. When Dick Clark’s American Bandstand came calling, she turned them down, too: they wouldn’t let Black kids appear in their audience. And in the end, she would even disappear from the stages of Toronto. She slipped out of the city one night after a show in 1971 and wasn’t heard from again for decades. There were rumours she’d been murdered. It would be forty years before a reporter finally tracked her down. In the last few years of her life, Jackie Shane would become a public figure once again, embraced by a city that was more ready than ever to celebrate her work. Today, she towers above Yonge Street as part of a twenty-two-storey mural commemorating the musical history of the Strip — and the remarkable decade when she graced the smoke-filled taverns of Toronto.
“I live the life I love,” she told the crowd at the Saphire that night, “and I love the life I live. I hope you’ll do the same.… As long as you don’t force your will and your way on others, forget ’em baby, you don’t need ’em.” In a city where homosexuality was still illegal, where the Toronto Police Morality Squad still stalked the streets, where queer couples would have to worry about their safety for decades to come, Jackie Shane was setting an example. Up there on that stage, self-assured and un-apologetic: a Black transgender woman who knew exactly who she was — and who wasn’t afraid to show it.
At the end of the night, as the band settled into a slow and sultry rhythm, Shane began to sing her most famous song. Her biggest hit was an old soul tune called “Any Other Way.” It would be recorded by several artists over the years. But the lyrics took on a deeper meaning when Jackie Shane was the one singing the words.
“Tell her that I’m happy,” she sang. “Be sure and tell her this: tell her that I’m gay. Tell her I wouldn’t have it any other way …”