Justin Trudeau has refused to rule out the existence of more pictures of himself in blackface as he said white "privilege" had blinded him to the racism of the practice.
Three separate cases of Mr Trudeau wearing blackface have emerged in the last two days, shredding his reputation as a liberal poster boy a month before the Canadian elections.
During a press conference on Thursday afternoon, Mr Trudeau said he "deeply regretted" the incidents, saying it was the sort of discrimination ethnic minorities "face on a regular basis". "I didn't see that from the layers of privilege that I have. And for that I am deeply sorry, and I apologise".
He declined to be drawn on whether further photographs may emerge, saying "I am wary of being definitive about this because the recent pictures that came out I had not remembered."
Mr Trudeau admitted he did not reveal the episodes to his Liberal Party during vetting processes when he ran for office, saying "I never talked about this. Quite frankly I was embarrassed".
The Canadian leader's political turmoil began on Wednesday night, when Time magazine published a yearbook photograph of a 29-year-old Mr Trudeau wearing robes and a turban, his hands, face and neck coated with brown makeup.
Then a teacher at West Point Grey Academy in Vancouver, Mr Trudeau was attending an Arabian nights themed gala dressed as Aladdin. In the few photos from the event, Mr Trudeau appears to be the only reveller wearing makeup.
On Thursday morning, Global News released an undated, low resolution video of Mr Trudeau wearing blackface, raising his hands in the air and sticking out his tongue. The Liberal party confirmed it shortly afterwards.
“Wearing brownface is an act of open mockery and racism. It was just as racist in 2001 as it is in 2019,” said opposition Conservative leader Andrew Scheer, adding that the prime minister is “not fit to govern”.
Addressing the media on his campaign plane on Wednesday, Mr Trudeau admitted he also “wore makeup” while performing Day-O by Harry Belafonte at a high school talent show, taking the number of incidents to three so far.
“I’m p----d off at myself, I’m disappointed in myself,” Mr Trudeau said during his apology. The prime minister said he did not consider it racist at the time, but knows better now.
Mr Trudeau dodged a question about whether he should resign, responding: “I think there are people who’ve made mistakes in this life and you make decisions based on what they actually do, what they did, and on a case-by-case basis, I think. I deeply regret that we, that I, did that, I should have known better but I didn’t.”
Mr Trudeau is widely seen as a leading exponent of multiculturalism and diversity.
Asked four years ago why he had nominated a gender-balanced cabinet, following his landslide election victory, Mr Trudeau famously responded: “Because it’s 2015.”
“This is the Trudeau brand imploding,” said Stephanie Chouinard, professor of politics at Queen’s University, of the images.
Popular support for Mr Trudeau has slumped this year following accusations he pressured his former attorney-general, Jody Wilson-Raybould, to drop a criminal probe into engineering giant SNC-Lavalin.
The company, which is accused of handing out bribes worth C$47.7m to Libyan officials between 2001 and 2011, employs more than 3,000 workers in Quebec, where Mr Trudeau's own electoral riding of Papineau lies.
In August, independent ethics commissioner Mario Dion accused the prime minister of violating Canada's ethics laws, while the Royal Canadian Mounted Police has reportedly been in contact with Ms Wilson-Raybould - who was expelled from the Liberal caucus in April - to discuss the matter.
Heading into the October 21 election, Mr Trudeau is currently tied with Conservative Mr Scheer in the polls.
With little public support for either candidate, the Liberal party has attempted to fight the election on social issues, accusing Mr Scheer of having archaic views on abortion and same-sex marriage and digging up dirt on conservative candidates.
“Trudeau has not been shy about contrasting his party’s image with that of the conservative party,” said Ms Chouinard.
Against that backdrop, many Canadians will see hypocrisy in Mr Trudeau’s blackface revelations.
Jagmeet Singh, leader of the third-place NDP, called the image insulting. “It’s about every young person mocked for the colour of their skin,” tweeted Mr Singh, who himself wears a turban.
West Point Grey Academy is one of several elite Vancouver private schools, catering to wealthy families in British Columbia, with annual fees of C$23,490.
Exclusive. Sources have confirmed to me that this is THE picture of @JustinTrudeau in blackface from high school that he referenaced in his press conference. From the year book at Brebeuf college. #cdnpoli He is singing Day Oh apparently. pic.twitter.com/ivBPoxbXi8— Evan Solomon (@EvanLSolomon) September 19, 2019
The gala Mr Trudeau attended – which also featured belly dancing, according to a 2001 school newsletter in 2001 – raised approximately $160,000 for the academy.
Earlier this year across Canada’s southern border, Virginia governor Ralph Northam refused to resign after admitting he had worn blackface, following the release of a yearbook photo.
The Liberal Party did not respond to The Telegraph’s request for comment.