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Eddie Cantor, right, appears in blackface in a scene with Ethel Merman from the Samuel Goldwyn film Kid Millions, circa 1935.Hulton Archive/Getty Images

The 100 or so costumed guests at the Halloween party were in a big rented hall in Edmonton huddled in groups, sipping beer and chatting when the lights went out. The opening strains of a Gladys Knight and the Pips song came over the speakers and a spotlight turned on, illuminating a group of young men who twirled and danced into the room lip syncing the song’s lyrics. One wore a red evening gown and a wig, the others were in rented tuxedos. They, like nearly everyone else in the room, were white law students at the University of Alberta. And they had painted their skin black as part of their costumes.

It was 1977. The crowd erupted in boisterous applause and cheering. Peggy Blair, then a 21-year-old law student, remembers the performance as the highlight of the party. It left such an impression that photos of it were published in the yearbook of Ms. Blair’s law faculty. This week, 42 years later, she posted those images on Twitter.

“I certainly didn’t hear anybody [at the time] say, ‘Oh my God, they were in blackface.’ That wasn’t on anybody’s radar,” she recalls from Ottawa, where she now works as a realtor. “It was, ‘Wow, that was a great party, look how many people showed up. Those costumes were wild!’”

After images of Liberal Leader Justin Trudeau wearing blackface on multiple occasions surfaced this week and caused a major diversion in the campaign for the Oct. 21 federal election, Ms. Blair, like many other Canadians, revisited her school days, looking to confirm vague memories of blackface worn by classmates or even teachers in recent decades.

While Mr. Trudeau has received widespread criticism for his use of blackface in 2001, researchers who have traced the history of blackface in Canada say the incidents involving Mr. Trudeau and Ms. Blair’s classmates are unsurprising blips in a long continuum. While the practice fell out of favour in film and television in the 1960s, it has been alive and well for decades and has merely shifted from mainstream entertainment to more private, elite and predominantly white spaces.

“What’s interesting to me is a lot of the most recent incidents are college- or university-educated white people in the context of their education. And they’re hiding it,” says Charmaine Nelson, a professor at McGill University who studies black culture in Canada.

In a statement released this week, the communications director of West Point Grey Academy, the school where Mr. Trudeau taught and which hosted the Arabian Nights fundraiser at which he donned blackface, said the event was meant to be “celebratory and respectful.”

“That said, we recognize cultural sensitivities have evolved over the past 18 years.”

Ms. Blair says law-school faculty would have been involved in preparation of the yearbook in which the photos of her classmates appeared, but recalls no resistance to their publication. She says she believes this is may be because no people of colour attended her law school at the time, so it was easy for casual racism to go unchecked.

“After all, there is nothing more elite than a law school," she said. It was only a decade later, when working in Ontario in the field of human rights, that Ms. Blair came to question the performance and understand why it was racist.

The origins of blackface trace back to 19th-century minstrel shows, when white actors impersonated black people in performances that drew on nostalgia for the days of slavery. These shows often featured violence against black people, who were depicted as lazy, uncivilized and unintelligent. Performers usually darkened their skin by rubbing it with burnt cork and drew on cartoonishly oversized lips.

“It was never meant to look like the range of brown colours of people from Africa; it was meant to be a grotesque mask,” Prof. Nelson says. “How ugly, how uncivilized are black bodies – that was the supposed humour for these white performers and their audiences.”

While completing a research project on blackface in Canada, Cheryl Thompson, an assistant professor at Ryerson University, noticed a quiet period in reported incidents after the 1960s civil-rights movement. But in the past two decades, reports have picked up.

“It doesn’t mean it wasn’t happening in the seventies and eighties," she explained; it’s merely that photographs from these events weren’t disseminated widely. "Then we get to the 2000s and social media. Everyone is like, ‘Where is this coming from?’ It never went away.”

A McGill database logging documented incidents of blackface in Canada includes 343 events from 1841 to 2016. The earliest occurred in Toronto.

In 2015, when Andréa Baptiste was a first-year McGill University student, she was sent a screenshot of a classmate’s Facebook post in which he was dressed as Kirikou, a West African boy who is the central character in a series of animated movies, for a film event. The classmate, a white man, was in blackface.

Ms. Baptiste, who is ethnically Haitian, and some of her friends confronted the classmate online, who responded defensively. He suggested Ms. Baptiste would likely wear white powder if she dressed up as Lady Gaga.

When discussing oppression in and out of school, Ms. Baptiste said, the focus was always on the history of Quebec and the oppression under anglophone rule. Because so many of the people she grew up with view the world around them through that lens, “when faced with someone’s oppression that’s different or worse, they will be quite dismissive,” she said.

Many of the events in the McGill blackface database since 2000 occurred at Halloween parties or frosh week events at Queen’s University, McGill University, Brock University, the University of Windsor, the University of Toronto and Wilfrid Laurier University, spaces Prof. Thompson and Prof. Nelson say epitomize privilege and elitism in Canada.

Joshua Aitkenhead recalls that in 2010, when he was attending Ambrose University, a small private Christian college in Calgary, a female classmate entered the school’s annual Halloween costume competition two years in a row in blackface: first as a basketball player she admired, then a rapper.

Mr. Aitkenhead said he was stunned as he watched her walk down a runway during the contest and observed fellow students laugh at the costume.

He yelled out, “Racism should not get a prize,” but never confronted the student directly, or complained to the school’s administration, something he says he now regrets.

“It was well-received,” he said. He recalls a few black students at the school, but found the population was far less diverse than it had been in Brampton, Ont., where he grew up.

Although Mr. Trudeau said he recognizes now that his use of blackface in 2001 was racist and the photos that surfaced this week were widely condemned, Prof. Thompson said she has little optimism that the practice will end any time soon.

“This is really more ubiquitous than we ever thought it was. I was shocked this frosh week we didn’t hear anything,” she said. “Halloween is coming. Let’s not hold our breath.”