Canadian Prime Minister Justin Trudeau has admitted that he cannot remember how many times he has darkened his skin with makeup while dressing up, as the scandal deepens ahead of next month's election.
Earlier, Mr Trudeau said he "deeply regrets" a photo which shows him dressed as Aladdin with darkened skin.
Two further images and videos of the Ottawa's leader have since emerged, leading to him conceding his privilege as an influential white man has given him "blind spots" to those who suffer racism and discrimination.
Addressing the number of times he had darkened his skin, the Prime Minister said he was "wary of being definitive about this because of the recent pictures that came out, I had not remembered".
The revelations have rattled his campaign in a tight election race.
Canadians will go to the polls on 21 October.
Mr Trudeau was photographed wearing a turban with a robe, along with dark makeup on his hands, face and neck to a costume party in 2001.
Trudeau, who launched his re-election campaign exactly one week ago, said he should have known better.
"I'm p***** off at myself, I'm disappointed in myself," Trudeau told reporters travelling with him on his campaign plane.
The image was taken at the school's annual dinner, which had an "Arabian Nights" theme that year, Mr Trudeau said.
The Canadian prime minister, who launched his reelection campaign a week ago, said he was dressed as a character for Aladdin.
He also revealed that it was not the first time he had darkened his face. Mr Trudeau admitted he had previously painted his face to perform a cover of Harry Belafonte's "Banana Boat Song (Day-O)" during a talent show.
Mr Trudeau added: "I should have known better then but I didn't, and I am deeply sorry for it.
"I'm going to ask Canadians to forgive me for what I did. I shouldn't have done that. I take responsibility for it. It was a dumb thing to do."
Mr Trudeau said he has always been more enthusiastic about costumes than is "sometimes appropriate."
"These are the situations I regret deeply," Trudeau added.
But with just a month to go until the re-election Trudeau's main opponent was quick to condemn his actions.
Andrew Scheer said "it was just as racist in 2001 as it is in 2019".
He added: "What Canadians saw this evening is someone with a complete lack of judgement and integrity and someone who is not fit to govern this country."
Another party leader who is a Sikh described the image as hurtful to victims of racism.
Jagmeet Singh, Canadian New Democratic Party leader said: "Seeing this image is going to be hard for a lot of people, it's going to bring up a lot of pain, it's going to bring up a lot of hurt."
"Please reach out to your loved ones, please reach out to people who are suffering in silence right now," he added.
Trudeau's reelection campaign in the balance
Liberal Party spokesman Cameron Ahmad confirmed the photo is of Mr Trudeau.
He says it was taken at the school’s annual dinner which had an Arabian Nights theme that year.
The photo’s publication could spell more trouble for Mr Trudeau, who polls say is facing a serious challenge from Conservative leader Andrew Scheer.
Mr Trudeau has been admired by liberals around the world for his progressive policies in the Trump era, with accepting more refugees than the United States.His Liberal government has also strongly advocated free trade.
But the 47-year-old son of late Prime Minister Pierre Trudeau was already vulnerable following one of the biggest scandals in Canadian political history, which arose when Mr Trudeau’s former attorney general said he improperly pressured her to halt the criminal prosecution of a company in Quebec.