How a Black, transgender woman from the American South took the local music scene by storm.
We tend to associate certain historical figures with a certain period of time, as though their thoughts and actions describe the general attitude of an era. Consider how many artists have been designated the “voice of a generation”, for example. On the other hand, we view some artists as “ahead of their time”. Jackie Shane, the American-born soul singer and one of—if not the first transgender musician to hit the charts in Canada and the United States—is definitely part of the latter category.
Jackie Shane combined the frenetic pace of rock and roll with the soulful energy of R&B to become one of the city’s most memorable performers of the 1960s. During shows at bars like the Saphire Tavern in the Financial District, Shane established a fearless persona that remained in the hearts and minds of the patrons long after last call. And between musical numbers, Shane celebrated her sex and sexuality with a confidence you would expect from someone in 2018, not 1968.
In fact, Shane’s music included terms and expressions unique to Toronto’s active but mostly underground LGBTQ2+ community.
Growing up in Nashville, Tennessee during the 1940s and 50s, Shane witnessed the birth and evolution of rock and roll as it spread around nightclubs across the United States. While still in her late teens, she moved to Montreal and joined fellow African-American musician Frank Motley and his backing “Motley Crew” band as a vocalist. They eventually settled in Toronto and established themselves as regulars of the nightclub circuit.
At the same time as Shane’s debut on the Toronto stage, musicians from across Canada and North America packed into sleepless taverns of Yorkville and the seedy cafes located along Yonge Street. Like Shane, musicians like Ronnie Hawkins moved to Toronto from America’s Deep South. A native of Arkansas, Hawkins was a regular at Yonge St.’s Le Coq D’Or and was instrumental in kickstarting the careers of Canadian icons Gordon Lightfoot and The Band. Meanwhile, future folk superstars like Joni Mitchell and Neil Young packed Yorkville’s coffee houses into the early hours of the morning.
But for all the similarities to the Canadian pop culture icons we know today, Jackie Shane’s experience is rarely included among them. While most performers hoped to get their big break in Toronto’s nightclubs, Shane’s success only extended beyond Toronto for a brief moment, even as her collaborations with local R&B musicians brought her to the cusp of stardom.
Partnering with fellow American musician Frank Motley, known for playing two trumpets at once, Shane recorded a series of singles, including her most famous hit, “Any Other Way”. At its peak, the single hit position #2 on the local CHUM radio charts.
For all the original hits and covers she made her own, Jackie’s “Any Other Way” is perhaps the song that represents her story the best. The cover of the William Bell hit peaked at #2 on the CHUM countdown and hit #124 on Billboard’s heatseeker chart. In the chorus, she sings: “Tell her that I’m happy, tell her that I’m gay, tell her I wouldn’t have it any other way.” This lyric is doubly interesting given the dual meaning of the term ‘gay’ in common parlance at the time. In fact, Shane’s music included terms and expressions unique to Toronto’s active but mostly underground LGBTQ2+ community. Though the lyrics were originally not a reference to her sexuality, Shane subverted the original meaning of the song to reflect her identity.
Advertisements for two separate Jackie Shane shows in Toronto that appeared in the Toronto Daily Star (Toronto Daily Star (1900-1971), Proquest)
Certainly, Jackie Shane’s uncompromising statement opposed the general public sentiment surrounding her. While some understood and supported her after witnessing her live, others couldn’t help but take issue with Shane’s gender. One reader wrote to the Toronto Daily Star asking if she was a man or a woman, only to have a journalist personally follow up with Shane.
In 1967, one of Shane’s performances at the Saphire was turned into a live album, Jackie Shane Live. Peppered with double entendres that hint at her sexual orientation, the live album showcases the importance of coded language in the face of bigotry. As one of the most vivid mementoes we have of her music, Shane interweaves her musical numbers with monologues as poignant today as they were back then. During Shane’s performance of “Money”, she sends a clear message to her haters about getting judged.
“You know, when I’m walkin 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. But you know, that don’t worry Jackie, because I know I look good.”
That being said, fellow band members observed general praise from Black Toronto audiences. In the book Any Other Way: How Toronto Got Queer, writer Steven Maynard pointed out that “appreciation might have started with Jackie’s undeniable musical talent, but the Black community took Jackie at face value or, better, with her face on. The Reverend Larry Ellis, former bass player for Frank Motley and His Motley Crew (as the band was known before the mid-sixties), explained that Jackie ‘didn’t hide that he was gay…People were falling in love with him knowing he was gay.’” ( It’s important to note that, at the time, while Jackie has revealed since then that she had transitioned, Shane and her entourage used the ‘he’ pronoun to identify her. Frank Motley said this before she had publicly transitioned).
Frank Motley, the bandleader who brought Shane to stardom (Toronto Star Digital Archive)