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The North American rhythm-and-blues circuit of the 1950s and ’60s had a surprising number of artists pushing gender boundaries. Macon, Georgia’s Little Richard, who’d once performed as Princess Lavonne in a traveling tent show called Sugarfoot Sam's, was certainly the best known. But Richard was heavily influenced by Esquerita, a flamboyant and feminine pianist from New Orleans.  Also from New Orleans were two other artists who were gay or transgender or nonbinary: Patsy Vidalia, born Irving Ale, hosted the city’s legendary Dew Drop Inn and recorded as Pat Valdelar; and gay soul singer and impresario Bobby Marchan regularly switched between male and female clothing—complete wi...

The Beatles changed the world in countless ways, but they also dramatically changed Toronto over three consecutive years of performances (1964 to 1966) at Maple Leaf Gardens. Almost overnight, the city was hit with a cultural shift of seismic proportions: Boys grew Beatle bangs, girls pinned photos of John, Paul, George and Ringo on their walls and parents worried about the sanity of their teenaged children. Canada’s folk darlings Ian & Sylvia had ruled up to that point, but as the male half of that duo, Ian Tyson, remembers, “the minute the Beatles arrived, it was over—well and truly over.” The folk boom slowed, as every kid on the block rushed to form rock bands. Toronto’s music scene ...

By the summer of ’67, Yorkvilleʼs hippies found themselves choking on exhaust fumes from bumper-to-bumper traffic. Reduced to curiosities for the passing, pointing motorists, many resented the way their community was being taken over by tourists gawking at the longhairs. Kids started demanding that Yorkvilleʼs streets be closed to cars. The Diggers seized on this and the issue became the hippiesʼ new mantra. Yorkville had been a thorn in the side of Toronto the Good for some time. But in the heat of that summer, the problems came to a head. Cops in the village started hassling kids with a “move-along, move-along” attitude. Politicians, meanwhile, railed against the presence of runaway youths...

Toronto has a long history of live music recordings, from clubs, coffeehouses and dance halls to football stadiums, hockey arenas and concert auditoriums. Some have been commercially released by record companies, while others have been secretively bootlegged by nefarious fans. The most legendary live recordings from Toronto have been those made with world famous rock, pop and blues acts like the Rolling Stones, who recorded parts of 1977's Love You Live at the El Mocambo club, where more live recordings have been made than anywhere else in the city. Others recording there include April Wine, Elvis Costello, Nick Lowe, the Cars, Big Walter Horton, Whiskey Howl, George Thorogood...

Jackie Shane broke all the rules. An American-born, black, transgender woman, Ms. Shane first came to Canada in the conservative early 1960s and won over audiences with her glamorous image and soulful singing. For the next decade, she packed clubs in Ontario and Quebec and landed one memorable song, the slinky, sassy “Any Other Way,” near the top of the charts. But then Ms. Shane disappeared and erroneous rumours circulated of a possible murder or suicide. For the next 40 years, the mystery grew until word came that the retired performer was living back in her native Nashville. Ms. Shane’s rediscovery resulted in a massive comeback that the former singer never planned – nor actively particip...